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The 7 Principles of an Operator

In my last post I wrote about how I figured out I was an operator. This post is about what being an operator looks like in the day to day.

In my career I have been most inspired by two famous operators. The first is David Sacks, whose essay The Cadence I have read maybe a dozen times. I keep a printed copy of it in my desk drawer. The other is Sheryl Sandberg, whose approach to scaling one of the behemoths of the modern tech world is the stuff of legend.

But Sacks, Sandberg, and most others who have written about running and scaling companies wrote from a seat of real authority. Most of us operating in the real world are operating without founder authority. The mandate is real, but the power is borrowed. We create order, momentum, and follow-through not by decree but by judgment, credibility, and persuasion.

So over my career I have collected a set of principles for operating under exactly that condition. Most of them sound like common sense. All of them are lessons from the real world. In the weeks ahead I will dig into each one with its own post.

1. Get it over the finish line.

Finishing is the only work that matters. Founding teams generate good ideas constantly. We should integrate with this new software. We should build this capability. We should stand up a proper CRM. We should set up profitability models. Yet none of these ideas returns any benefit until it is completed, implemented, and operationalized.

Teams have their own version of the problem: everyone loves starting projects, and far fewer love shipping them. Many organizations have a graveyard of dusty projects that made it to eighty percent and no further.

The operator is the one who puts in the effort to get something from eighty percent to done. The operator also understands two uncomfortable truths: something eighty percent done can be as useless as something never started, and the last ten percent can take more effort than the first ninety.

2. Understand the problem before reacting to it.

People tend to react to problems instead of understanding them. It feels good to fire off an email or make a quick decision the moment a problem lands. Founding teams face a flood of random problems daily, and over time the overwhelm builds until clearing the plate becomes more attractive than sitting with what is actually on it.

The trouble is that a problem reacted to is a problem passed on at full size, or larger, because the reaction adds alarm on top of substance. Every problem that moves through a person comes out one of two sizes: smaller, because they took the time to understand it and handed on the manageable version, or bigger, because they added their own urgency to it and passed the weight downstream.

The operator’s role is to create the process, and enforce the discipline, of taking a beat to fully understand a problem before reacting to it. The mechanism varies, but the simplest version is often just to keep asking what we are actually trying to solve for until the answer makes sense. Done consistently, this is what it means to lighten the load: absorb the noise, pass on the signal, and make sure problems shrink as they move through you rather than grow.

3. Act on signals while stakes are still low.

Every serious problem announces itself early, quietly, while it is still cheap to address. Acting on those early signals is thankless work, and the operator who insists on it risks looking like a pedant.

Early action costs real time and effort on a problem that might never materialize, which can make the operator seem paranoid, or worse, a waster of everyone’s time. And when prevention works, the disaster never arrives, so nobody thanks you for a fire that did not happen. The counterfactual is invisible. You pay the cost in full view and never collect the credit.

But this is the role. Anticipate the pitfalls and sound the alarm, because once a crisis actually arrives, it is almost always worse and lasts longer than anyone expected.

4. Make a move when the cost of waiting exceeds the cost of being wrong.

Standing still is as much a decision as making a move. The discipline is to weigh the worst case of holding the status quo against the worst case of acting. Some problems compound while you deliberate, and for those, hesitation is not prudence. It is the most expensive option on the table.

Ask two questions of every stalled decision: what does waiting cost, and what does being wrong cost? When the first number clearly exceeds the second, move. You will sometimes be wrong, and being wrong will cost less than the waiting would have. This is not recklessness. It is taking the asymmetry seriously instead of treating all caution as free.

5. Fix the system instead of firefighting.

Many leaders are secretly addicted to firefighting, because being needed feels like being valuable. It is a trap. If a problem shows up repeatedly, the part of the system generating the problem is what needs fixing. That fix can be as complex as upgrading a key piece of infrastructure or as simple as giving customers better training so the problem stops arriving at your door.

6. Lead with clarity, not pressure.

When someone is stuck or a team is underperforming, the tendency is to apply pressure: more urgency, higher stakes, a tighter grip. It can work briefly, and it costs permanently, usually by burning out the team. The better lever is almost always clarity: help the team understand what good looks like, and who owns what. Most underperformance is not a motivation problem. It is an ambiguity problem.

7. Let the data shape the narrative, not the other way around.

Organizations run on stories, and stories can trick us into believing things are how we wish they were versus how they actually are. Sometimes activity gets reported as progress, or a forecast gets built backward from the number someone hoped to hit, or strategies assume everything will always go right.

The operator’s job is to hold the line between what is verifiable and what is merely the stories we tell ourselves and each other. Ask for the primary source. Pull the real numbers. Let them overturn the preferred story when they do. Because decisions built on evidence fail differently, and more rarely, than decisions built on narrative.

All seven principles, taken together, are about creating order, maintaining momentum, and keeping the team productive and calm from a seat that earns its influence rather than inherits it. Over the coming weeks I will take each principle, discuss in detail what it looks like in practice and how you can incorporate it into your day to day to build your operator muscle.

How I Learned I Was an Operator

When someone wants to change roles, there is usually something visibly wrong with the job. The pay is too low, the politics are exhausting, the workload is crushing. My case was stranger. Nothing was wrong. I was rated well, paid fairly, and surrounded by good people. Yet every two to three years, I needed a change, and I could not have told you why.

Until now.

Looking back through the last fifteen years, I can see that every time I moved to a new role or a new company, I was answering the same three questions:

Capacity. Does the role use everything I can give, or only a small part of it?
Authority. Can I act on what I see, or only observe and report?
Impact. Does the work I do multiply, or just add?

When all three are present at once, I am fulfilled. When I run into the limit of any one of them, I feel I have outgrown the vessel, and it is time to find a new one.

My whole career, it turns out, was the slow discovery of these three variables, one at a time. And I had to reach each limit before I knew it was there.

Capacity: the analyst years.

My first job out of university was as a business analyst on a risk-rating application.

I walked in knowing just about nothing. Nothing about risk management, nothing about requirements, nothing about how any of it fit together. But by the end I knew the app and the project as well as anyone else in the room.

That arc, drop into something I do not understand, absorb the whole of it, become the person who holds it, would repeat at every stop for the next fifteen years.

The analyst seat was sized for a fraction of what I had to offer. While I could do the slice very well, I could also do a great many other things.

Many large organizations are built so that a defined role stays defined no matter how much more you bring. It is simply the nature of big institutions, especially in the carefully governed, heavily regulated verticals.

And each time capacity became the limit, what I felt was restlessness.

Authority: the program years.

When I progressed from analyst work to program work and took over a portfolio of improvement initiatives, I found myself running things rather than analyzing them. This was a good fit. For a while it scratched the real itch and I loved making things run better.

But it introduced a constraint I had not met before: lack of real authority over the system.

I could redesign the processes but not the tools and not the people. I could write the requirement strategy but did not have the authority to operationalize it or change the framework.

I could see a better way forward, but was unable to act on it. Even when I could see clearly what would make things better, moving it from idea to reality depended on far more than my own effort.

For what it is worth, I was good at these roles. I moved from a pod lead to a program lead within months of joining one of them, with a top rating in my first year, for example.

The limit I kept reaching was never about whether I could do the work. It was about how much of what I could see was mine to shape. And the lack of authority translated into a feeling of being stifled.

Impact: the thing I did not know to look for.

Eventually I was pulled into a seat that handed me the first two dimensions.

I joined a startup a few years into its life and took on its strategy and operations leadership, with a place at the table for every major decision. The container could finally take everything I had, and I had the room to act on what I saw. For the first time in my career, both boxes were checked.

And checking them taught me there was a third box I had only just begun to understand.

I call it impact, but impact can mean many things. There is one-to-one impact: I put in an hour of effort and yield a benefit proportional to, or slightly higher than, what I put in. I have had plenty of those, and they were deeply satisfying.

But there is a second kind that I am just beginning to learn about. The kind where an hour of effort does not move the number by one unit, it moves it by ten, because of where the business sits and what that effort sets in motion.

For instance, restructuring a pricing matrix thoughtfully can reset the margin on every future dollar, while building a new system of processes, tools, and training can let a company take on ten times the volume without ten times the cost. This is work that bends the trajectory of the P&L rather than improving a single line on it. The same work compounds in one business and just adds up in another.

I expect to spend the next few years figuring out how to create multiplicative impact: not just add to the P&L, but multiply it.

So the three are a kind of diagnostic I now carry through my career. If I feel restless, I know capacity is the limit and my skills are not being fully used. If I feel stifled, I know I lack the authority to fix the system. And I am still learning what it feels like to run into the limits of impact.

What I actually am.

Over the years I tried on the labels. Analyst, delivery lead, product manager. Each fit partway, and none fit all the way. Putting it all together: what I am is an operator. The person who holds the entire system in view and makes it run better. Who fills the gaps, turns chaos into order, and multiplies the effort of everyone around them.

The analyst’s systems thinking, the delivery lead’s results, the product manager’s ownership, all of it, plus the one thing none of those seats had on its own: a mandate to see the whole board. It is what the org chart sometimes calls business operations, or strategy and operations. I think of it simply as operating.

And I had been operating the entire time. I just kept doing it inside roles built to use a fraction of it, in places that did not have a single seat for the whole thing.

In my next post I will write about what it means to be an operator, especially an operator without founder authority, and the seven principles I believe every operator needs to internalize.

Corporate Life 101 – 7 Ways to “Seem” More Likeable

I didn’t fit into the Canadian corporate world naturally in the beginning.

I am unapologetically myself and more than once “myself” was not corporate enough right away.

In my first job at the Bank, one of my bosses compared me to Elle Woods (from Legally Blonde) – which I *think* he meant as a compliment but sure didn’t feel like it at the time.

I was also referred to as “quirky” by another former boss – again definitely not meant in a mean spirited way, but still not quite a compliment either!

And I consistently struggled with tempering my natural intensity to “get going” with a polished “sweetness” that many corporate environments demand.

As a result, MANY times in my early years I was told to “tone down the passion” when having challenging conversations. I misunderstood their meaning at the time, what they meant was the emotions in my voice was making people uncomfortable.

I know I am not alone. Many of you I spoke to struggle with a version of this every day.

(Btw, being “unlikable” as a woman is more detrimental than being unlikable as a man as I have seen male colleagues get away with being far more contentious and aggressive than I was EVER allowed to be)

Regardless, like most things in Corporate Canada – it’s not hard to manage perception, if you have a strategy!

And by the end of my bank career, I amassed enough techniques to navigate the conflict-shy corporate culture, and I was able to maintain my edge without ruffling many feathers.

In this post I’ll share my strategies for appearing more likeable in a corporate environment, without fundamentally changing who you are.

I hope you find some of my strategies helpful!

Channeling an alter ego

I spent my last year at the Bank in a high visibility, large program with several workstreams and a myriad of personalities. Tensions ran higher than usual.

I was in a leadership position and was often asked to opine on strategies or handed deadlines well outside the scope of my control.

What helped me get through these stressful meetings with dozens of people, many of whom in a position to fire me, was “channeling my inner-Stella”.

Stella (a real person but I am using a pseudonym) was a stakeholder in my program with the calmest, most radio-friendly voice I ever heard!

She was pleasant, always spoke in a lower register, carefully enunciating every word. And Stella could get away with saying almost anything without triggering defenses in others.

So, I started practicing my Stella voice!

And whenever I felt I needed to deliver a difficult message or ask a challenging question – I stepped into my inner-Stella. Immediately, I sounded calmer, softer and less confrontational.

Lowering voice and slowing down speech automatically makes things less confrontational, but easiest for me was to actually mimic a real person and make her my alter ego.

It’s sort of the opposite of Beyonce’s Sasha Fierce.

I found consistently channeling my inner Stella in difficult situations allowed me to maintain a “chill” reputation in an easy and fun way, without impacting my sharpness or edge in other areas.

Managing REACTIVE days

I occasionally still have days when I am more reactive than usual, my triggers are inadequate sleep, working too long for multiple days (past 6pm) and missing weeks of workout sessions.

On these reactive days, channeling the inner Stella is not enough.

It is best to go remote, reschedule challenging conversations and keep interactions with others to a minimum.

In a corporate environment we superficially interact with dozens – maybe hundreds – of people over the course of a year. Unlike friends or family, one negative encounter on a bad day can leave a lasting impression on a colleague who doesn’t really know us well.

In my opinion, it’s best not to risk a public display of reactivity and limit interactions as much as possible on “reactive” days.

Important caveat here is I am very disciplined about getting enough sleep, avoiding working very late (better to start earlier) and being consistent with my workouts, so bad days are the exception and not the norm.

Offering to Do coffee runs

One of my favourite ways to appear more likeable is to get people coffee!

Corporate Canada has some of the most over-caffeinated people in the world and they LOVE it when you bring them back a coffee. Especially if they are stuck in a meeting and can’t go themselves.

I ALWAYS offered to grab coffees when I went for one myself during my Bank days. In fact, I had informal agreements with several colleagues to bring back coffees for each other.

There is also something “intimate” about knowing how someone takes their afternoon caffeine. I still remember one of my former colleague’s coffee order – double espresso with raw sugar at Starbucks- and it was a superficial bond that made our other discussions more palatable.

Writing nice, polite & pleasant emails

Most of our conversations in the corporate world happen via email and over time, just putting in a touch of niceness in the emails can make a difference in how likeable we seem to others.

Any time anyone mis-spelled my name in an email, for example, I instantly disliked them a tiny bit.

We underestimate how much likeability we can exude by just being “friendly” in our emails, consistently and deliberately.

Writing “nice” emails include:

Writing the recipients name correctly! For example if someone goes by Jen, for heaven’s sake don’t call them Jenn!
Include a hello/hi – a greeting of some type, before jumping into the email. I like a sunny Happy Monday or something that is not immediate cringe-inducing for you.
NEVER randomly ask a person to do something without providing context. It is just rude to ask for something without adding “why” in a corporate environment – even with a subordinate (today’s subordinate is tomorrow’s boss).
Say thank you often (more than necessary) and use at least one random “!” – I don’t know why, but ! in an email just ups the likeability factor (hey, you’re the one who wants to be more likeable!).
Remove any sign of passive aggression – even if you feel it. No “as per my last email” or unnecessary escalations. Your pissed-off-ness is your problem, not poor “Joe the Infrastructure PM”‘s – trust me, he does not care.

Saying specific and nice things about people to other people

One way to be instantly likeable is to say very specific, very nice things about your coworkers to others.

Specificity (and sincerity) is important because a blanket “omg they are so great” is useless and counterproductive. Because the person you’re saying that to may not agree with a general statement and you will surely come across as phony if you overuse it.

Instead pick an ACTUAL nice thing and instead of spraying “omg, Jen is so great!” (which people do ALL the time) say something like “I really liked working on building that deck with Jen, she was so organized and great with visual storytelling”.

In this case, even if Joe thinks Jen is terrible, he can’t deny Jen’s story telling skills. And you come across as astute and kind.

Avoiding complaining AT ALL COST

This one is CRITICAL in a corporate environment.

DO. NOT. COMPLAIN. ABOUT. COWORKERS. TO. OTHER. COWORKERS

Do not do this. Never, ever, ever.

If you must complain or vent, find a secret friend. Best if said friend doesn’t even work at your company.

I have not historically been guilty of this, but I’ve seen people kill their careers with this bad habit.

DO. NOT. COMPLAIN. ABOUT. COWORKERS. TO. OTHER. COWORKERS. EVER.

Making genuine connections with people

This last one is simple. Make some office friends with other likeable people.

Let people see you laughing, talking and enjoying yourself.

Smile. Make Jokes. Join the gang in the kitchen to eat leftover food.

Lighten up.

When in doubt, bring some cookies & feed people.

Finally, remember it is JUST work.

A final note about being “authentic” at work.

Those who genuinely care for us and love us – like friends and family, deserve our authentic selves. Our authentic selves are a gift of vulnerability and humanity that we bestow on special people.

However, there is no need to spring our moment to moment frustrations and/or misery on unsuspecting coworkers in the name of authenticity.

They have lives, problems, burdens that they are also dealing with and they did not sign up to be harassed by our “authentic selves”. Many people in corporate are there to collect a pay check so they can go back to their lives, accept it and respect it.

The good thing about a corporate job is you can always switch to a different role!

A Framework for Making New Friends as an Adult

A well-known psychologist I follow on Twitter posed a question the other day “How do adults make new friends?”

It wasn’t the first time I heard this question.

One of my girlfriends said that it was harder to make new friends as an adult than find a partner.

I may struggle with a lot of things, but making friends is not one of them!

So as a friend making enthusiast, I wanted to write a starter post for those out there struggling to make new friends as an adult.

CAVEAT: This is just ONE woman’s opinion/process – I am sure experts have written many books on this topic, so for something formal and well-researched – feel free to buy a book.

First my Expertise

I was born in Bangladesh and was a shy child.

I had strong bonds with my cousins and a handful of good friends in school. But I left EVERYTHING behind when I moved to Saudi Arabia at age ten-ish. Then I spent the next 5-6 years rebuilding new friendships – in English (a language I didn’t speak at the time), only to immigrate to Canada to restart the process.

My extraversion and easy ability to bond with people is one of my few super powers. And while it doesn’t help me in practical ways, as friendships must never be transactional, my friendships bring enormous pleasure, joy and dimension to my life.

So with that preamble, here is my “Five Step Framework” for making new friends as an adult:

First, decide WHO is qualified to be a friend.
Then, cast a wide net.
Be open to making the first, second & the third “move.”
Then, decide on friendship “potential”.
Finally, nurture the relationship

First, decide WHO is qualified to be a friend

We are not for everyone. And everyone is not for us.

This is a good thing because only the “beigest” of us would be universally palatable.

We can save a lot of time and heartache if we first think about who we want to let into our lives in an intimate way.

I will share my criteria below. Keep in mind everyone needs their own criteria, based on their own morals and values, but it’s important to have a set of criteria because time and energy is finite.

1. I am ONLY friends with people whose company I find uplifting and joyful.

My friends are people I genuinely, deeply like and feel I can be “myself” with. All my friends are kind and intelligent.

They are also strongly opinionated and secure in themselves. So they don’t fall apart or get resentful if I express my own strong opinions.

I walk away from most interaction I have with them feeling good, healthy and connected.

2. I am ONLY friends with people for whom I also bring joy and value.

I fully accept that not everyone will like me.

So the only people I invest in are those who also feel joyful and uplifted in my genuine presence.

Otherwise, I move on and find those who do enjoy my company.

3. I don’t fear giving more, doing more, saying more and loving more.

I try not to care about equal reciprocation.

I am fine if my friend does not return a text because she is busy. I don’t mind going the extra mile for someone’s birthday and not have that returned.

I am happy to check in first, to make the plans, to meet more than half way (metaphorically and practically), and to make more time.

None of the above I do out of guilt or obligation: I need my friends. I am happy to invest in my friends. And I also fully accept everyone will have practical and spiritual ups and downs.

4. However, I WILL redraw boundaries that no longer work for me and toxic behaviour is a deal breaker

If I feel I can no longer be myself around a friend, and it doesn’t matter why, I redraw my boundaries.

It can mean I reduce how often I see them, or the type of activity I do with them, or it can mean respectfully ending the friendship entirely.

I give my friends benefit of the doubt but also any display of toxic behaviour – such as passive-aggressiveness, talking behind my back or silent treatment is usually a one way ticket out of my life.

Then, cast a wide net

Since I only have four criteria for friendship, literally every person I meet is a potential friend.

I have wonderful friends whom I’ve met through work, through other friends, who are parents of my children’s friends. I even have a friend I met randomly while waiting in line to vote (I ended up attending his wedding a few years later).

I typically don’t look for common interests while making friends, and simply focus on character. I have enough breadth of interest that I’ll eventually find something in common with a new friend.

It’s also fun to be introduced to random hobbies by a friend (e.g. CrossFit and Salsa dancing) and fail/succeed together at it.

Many people try to find friends via shared interest which actually may be limiting unless their lives revolve fully around that shared interest.

For those looking for new friends, it might be easier to find a person whose character meets the friendship criteria first THEN find common interests to share.

Be Open to making the first, second and the third move

Most people make the mistake of trying to connect one time and then dropping the relationship if there isn’t any reciprocation.

As a successful friend maker, I suggest initiating at least three times before giving up on a potential friend.

It can look something like this:

Move one – Say hello and start a conversation.
Move two – If you like them, ask them for coffee/drink.
Move three – If that goes well, suggest a third thing (e.g. visit to a museum).

By the third thing, it’s obvious if there is enough raw material for a friendship.

In my case I try to evaluate if they are kind, intelligent, and fun. I see if they like me and find me fun. Most importantly, I see if I can relax around them and say what I feel, without eliciting an unexpected reaction.

Key here is to evaluate if the person meets our own criteria for friendship. It’s not about feeling rejected, rejecting someone or overthinking.

Then decide on an intimacy potential

Not everyone can be or want to be your “bestie”, even if they are super awesome.

Some friends will only be good for a group hang. Some friends you will see regularly for a specific activity (e.g. bi-monthly museum visits).

Some friends will feel like life-long soul mates.

Trying to evaluate where this person may fit will give you an idea of how much effort to put into the relationship.

It’s okay to think someone could be your best friend and later realize they’re not, and vice versa. This step is only needed to understand how to divide your attention in the beginning.

Finally, nurture the relationship according to the intimacy potential

After my family, my “life long soul mate” friends are my highest priority. I exert consistent effort to make them feel appreciated and cherished.

Not just through words but with actions of showing up for their life events big and small, celebrating their milestones, and providing support through their hard times.

For all my friends, I check in with them regularly. I make plans to see them. I share articles, news or memes based on their interests. And over time, the relationship blossoms into something special.

Making new friends as an adult can be done with the right mindset – it just takes time and consistent effort. The critical piece is to nail down the type of person we want as a friend, then investing seriously in those relationships while letting go of the rest.

1 Year Review: A New-ish Me

^{I took this selfie in Miami at the All-In Summit 2022 – my first tech conference since Grad school.}

I left a decade plus bank career in 2022 to join Pllenty – a fintech “startup” in it’s 7th year. Join me as I reflect on how the last year shaped me. I wrote about the five things I love most at Pllenty in my previous post. In this post I look at how I have changed as a person as a result of my career shift.

The work we do shapes who we become.

When I started my career in 2007, I interviewed at three different jobs:

One was at a small marketing agency.
One was at the Provincial Government.
One was at BMO’s Technology group, where I was hired.

If the first two jobs worked out, I would have been a VERY different person today.

When I left my bank job in 2022, in addition to doing something different, I knew I wanted to also BECOME someone different.

My role at Pllenty is flexible enough to let me explore paths completely closed to me at the Bank. And within a year, I am already different from who I would have been if I spent this last year at the Bank!

I am now a person who knows a lot about the Canadian non-profit landscape

Last year this time I knew almost nothing about Canadian non-profits. I donated to several organizations and had cursory awareness of the United Ways and YMCAs of the world. That’s about it.

Over the last year I have learned an incredible amount about charities in Canada. I learned how they help build communities and the nearly insurmountable barriers they face everyday.

Canadian charities are especially underserved technologically. Not just compared to the for-profit sector but also compared to US-based charities.

As a result, I have a worthy mission to enable Canadian NFPs exceed their fundraising goals while helping Pllenty become their number one tech partner.

I am a now a person who knows how to collaboratively build usable software (with the dev team)

I spent a chunk of my career as a Business Analyst – so providing requirements and testing things were always in my wheelhouse. However, I had minimal control over what the final products looked like or how quickly they were delivered.

I don’t code – so I hesitate to take too much credit here.

Yet, over the past year, I learned how to work with a solid dev team to produce usable, elegant software – with real life utility – quickly and efficiently.

Building capabilities real people use every day is so satisfying, especially when working with a bad-ass team.

I am a now a person who is growing a network of social innovators, technologists and entrepreneurs

I love my banker buddies. Nothing will ever change that. And I respect the hell out of what they do and the value they bring to society.

When I first left the Bank (and 80,000 colleagues), I was shocked by how tough it was to meet new people. Pllenty has a small team (half of them are well under 30) and except for a few partners, for months I didn’t get to meet anyone new.

As a result, I started to host and attend networking events and conferences. It is still so tough to build a meaningful relationship based on one shared drink at a vendor holiday party. But slowly I am beginning to feel like part of a community.

And this new community of people are those making daily dents in the world by starting charitable organizations, building a startup or investing in cool companies.

In the up coming year, I plan to continue to grow my network and contribute to this community even more.

I am a now a person who has a business partner

Dan Lee, the CTO of Pllenty, is a friend of almost 20 years.

I’ve known him through his wild University days, the young entrepreneur days, I partied at his wedding and our sons are now close friends.

But over the last year, we developed a business partnership.

Just like how life is better with a fabulous life partner, work is better with a fabulous business partner!

We compliment each other’s blind spots. Have mutual respects for our skillsets. We are aligned in our vision of excellence. And we are learning when to apply pressure… but also when to back off.

For the first time in my career, I feel like I am going to “make it” (whatever making it means) and Dan is a big part of this.

I am a now a person who is not calculating vacation days and retirement plans

I remember 10 years ago writing my ideal retirement age down, then working backwards to see how often I would require a promotion to save enough money for retirement.

Even last year I was calculating how to strategically use vacation days to maximize 4-day work weeks.

All that calculating stopped when I joined Pllenty.

I still LOVE going on vacations but I no longer NEED to go on vacations.

I don’t have the need to calculate anything as I am focused on a very different process of learning, creating, and growing.

I enjoy my job Pllenty. I was perfectly fine with my Bank job also. But now I feel I am at the start of the right journey and I don’t care about the end.

1 Year Review: 5 Things I love about Working at a Small Company

^{My first work selfie that I ever posted to my socials, after a project for Terry Fox Foundation.}

I left a decade plus bank career in 2022 to join Pllenty – a fintech “startup” in it’s 7th year. Join me as I reflect on how the last year shaped me in my next few posts.

I want to start this series by describing five ways my role at Pllenty brings real satisfaction to my day-to-day, most of these I think will resonate with anyone working for a small company.

Making easily identifiable Impact

It is tough to measure the influence one person has on a corporation. We tend to celebrate corporate wins as large groups, without truly knowing how our individual acts led to a specific result.

At Pllenty (and I suspect in most small companies) it is very easy to trace one’s activities to an outcome. As a result, I can see how even my tiniest action directly link to a positive result for the company.

I review a form for five minutes, it leads to a bug fix earlier in the process.

I tidy up a slide from an old deck, it enhances all future presentations a little bit.

I read a case study on a fundraising campaign, we improve a small step in the donor experience.

Any time, any of us at Pllenty take ANY action correctly, it makes a visible positive difference, often creating a virtuous loop that is quite satisfying.

2. Constant, Sustained Momentum

A small company relies on finishing things quickly, so every team member is invested in speed. A very full plate with many deadlines looming is the stuff of sleepless nights.

So, communication happens fast.

Decisions happen fast.

Work happens fast.

We measure things in hours and days. Not weeks and months.

It is a state of existing, not for everyone but exhilarating for those who truly thrive in a “fast paced environment”.

3. Sweating only the leverageable Stuff

I no longer have time to do one-off things to perfection.

Every task I spend a lot of time on are all leverageable for the future- either directly (e.g. enhancing the way we onboard clients) or indirectly (e.g. learning about peer to peer fundraising platforms in Australia).

All other tasks fall into the adequate bucket.

4. Intense and Genuine Teamwork

When the team is small, each relationship becomes personal – for better or worse.

When someone is sick, there is genuine concerns. Conversations are have inside jokes and sentences often start with “remember when…”

Politics does not exist, because masking around the same 5 people is exhausting and unsustainable.

On the flip side, it is easy to accumulate frustrations and beefs.

Everyone remembers the “historical context” for every f*ck up. And we all know who “screwed up” when things fall apart.

However, as we know ~60% of startups fail within the first three years. Which means behind every startup that succeeds, there is ALWAYS a team of exceptional people.

Pllenty is now in it’s 7th year of surviving (and growing) and it is truly because of the exceptional individuals I work with.

And I get to work with them, learn from them, help them, support them while seeing their blunders and idiosyncrasies (and displaying mine) every day!

Even on my worst day at Pllenty, I can’t think of a better place to be.

5. Finally the Anti-boredom

I have never been this NOT bored in my life.

Even when I worked in Cap Markets risk management, arguably one of the most stressful (non front-office) bank jobs with OSFI breathing down our necks, I had days when I did little or something repetitive I didn’t want to do.

These days I have the opposite problem. I need to watch out for not burning out because of working too much.

Working with a small team with high daily stakes, there is ALWAYS a new, random challenge. Literally every day at work in my past year with Pllenty, I learned something new.

In my next posts I will describe some of the potential downsides of working at a small company and describe ways I was able to grow in this very different environment.

My Own Personal Career Pivot – Part 3

In part 1, I wrote about the early days of my career – starting at BMO and then at TD.

In Part 2, I wrote about finding out what was next and reaching my immediate financial
goals.

In this post I’ll describe the steps I took to leave the corporate world and join a start-up and end with my evaluation process.

By the end of 2021, I had set up a secondary revenue stream via my condo and bought the house I planned to live in for at least the next decade. I also sold my old house for more than expected and used the extra money to set up an emergency fund and improve my savings.

I was ready to focus on my career and take some risks.

In part 2, I wrote about exploring consulting to earn extra income and expand my skillset. During that exploration period, I became deeply familiar with two companies.

The first company provided recreation services to children, looking to spin up a tech arm to rebuild their software. And the second company was a fintech start up with a payment and communication platform, branching out to work with larger NFPs.

Both companies had innovative, hardworking founders with an interesting vision for the future and a history of success. However, it was clear to me that I was a better “fit” for the fintech company – even compared to what I was doing at the Bank.

That fintech company was Pllenty, where I currently work!

I had access to inner workings of both companies through my personal network. And the more I learned about Pllenty, the more I felt this COULD be the place for me!

So, at a 1-1 with my contact at Pllenty, I expressed my interest in working with them “one day”. I didn’t know exactly when that “one day” would be. But I followed up regularly with my contact throughout the next months to keep my interest top of mind.

The more I learned about Pllenty and the payments, the more I liked what I was learning and wanted to learn more. For example, after having an in-depth conversation with my contact about the payments space, I joined a Fintech book club online and bought my first book on payments (Anatomy of the Swipe).

However, when I received the call from my Pllenty contact winter of 2022 for a potential job opportunity, I totally wasn’t ready!

At TD, I had an awesome salary, a fabulous boss, a leadership position in an interesting and career defining program rolling out Salesforce. While I wanted to take a career risk, I didn’t expect to cross that bridge for at least another 18 months!

I had been gathering intel on Pllenty for over three years, so I HAD to explore this opportunity now that it had presented itself.

I kicked off the exploration process with some real talk with my Pllenty contact. I asked probing questions about what was working and what was not working. I asked about the team and who they were. I asked about the history of the company and the vision for the future.

Then, I put myself forward for a conversation with the President & COO of Pllenty. He was an acquaintance and already a person I admired and respected. But in our 1-1 I was blown away by how he was able to walk me through the past, present and future of the company in a 45-minute conversation. For me, this was a sign of a leader who wanted to go somewhere, and I felt excited to be part of the journey.

After I felt “the feeling”, the rest was an exercise in satisfying the rational parts of me and identifying blind spots.

I had a solid career trajectory at TD but at Pllenty I had a tremendous chance to grow as a leader more immediately.

TD provided me with stability and predictability, but Pllenty will provide exposure to all parts of a business – from the early sales calls to discussions on infrastructure.

I would be more vulnerable at a start-up if things didn’t work-out, but I also had a chance to be participate in tremendous upsides if they did.

As part of the blind spot evaluation, I had an hour-long conversation with my smartest and most brutally honest friend with a tech background and whatever downsides they could come up with didn’t sound all that bad.

I am not privy to what the conversations were like on the Pllenty side. But both parties saw a fit, took a chance, and I was offered a job!

I gave my start date as April 18th to allow me 3 weeks of notice at TD, plus two weeks off to decompress.

That was now 3.5 months ago, and I haven’t looked back! It has been an intense ride so far and I enjoyed almost every moment of it.

Looking back, I can summarize my evaluation process (whether to stay at TD or join Pllenty) from three angles:

1. Financial

My medium-term financial goals such as buying real estate and a substantial emergency fund were all met before leaving the Bank. If I still had such financial goals, I may have tried deferring the move for 1 or 2 more years.

I also focused on adequate cash-flow vs total compensation to ensure we could maintain our current lifestyle (e.g., equity vs salary). Taking a big pay cut in exchange for more equity, for example, would not have worked for me.

Finally, I looked 5-10 years ahead and saw which would bring me more upsides. I felt that while steady ladder climbing at the bank would be great, I had a higher chance of being part of something more rewarding in the long term by joining Pllenty.

2. Flexibility

Pllenty offered more flexibility of working hours compared to the bank.

Most of my meetings at Pllenty are concentrated between the hours of 10am and 4pm, Tuesday to Thursday. So, by working a few hours on the weekend, I can significantly improve the flexibility of my days outside of those core hours.

I also influence the efficiency at Pllenty, as we are a small team. So I feel more confident that I can continually improve efficiency over time in ways impossible within a complex corporation.

3. Growth

Finally, the nature of a start-up offers tremendous opportunity for growth. Any problem that occurs in the company, we need to solve ourselves – there is no X department (looking at you TRMIS) we can do an intake with. Additionally, origin of every mistake is painfully obvious – so there is no where to hide either.

I find that I have learned something new literally every day since I started, and I have not scratched the surface of all there is to learn.

That’s it! I hope you enjoyed my three part journey from a Corporate lifer to a start-up “newb”.

Thanks so much for reading, please keep reaching out with your comments and questions.

My own Personal Career Pivot – Part 2

In part 1, I wrote about the early days of my career – starting at BMO and then at TD. In this post I’ll get into the critical three years where I achieved my financial goals and started thinking about what was next.

In 2018 I was 37, my sons were out of the baby stage, my mortgage was well under $100K and I began to wonder what the next stage of my life will look like.

I started simply by listing out what I wanted to do more of: writing, travelling, and meeting new people. And I analyzed how much money I needed to support a
comfortable lifestyle for myself and the family.

I gave myself three years (or until 2021) to figure out how I was going to get there. The illusive goal was to make more money while also having more time to write, travel and meet new people.

First, I explored increasing my income by doing 10 hours of consulting work a month, in the evenings and weekends. I set my rate at $75/hr and started asking friends if their companies needed some help.

I quickly learned that working longer hours for more money aligned poorly with my overall goal.

Also, once I started a project with a company, 10 hours/week of sporadic work was not enough time to do a good job.

Finally, TD had policies against moonlighting, and I wasn’t sure I wanted this extra money enough to deal with the “paperwork”.

So, I went for door #2: that is get paid more for my 9-5.

Once I made the decision, it was a relatively easy process. I applied to several internal positions and then landed a new role at TD that paid more, with a higher bonus and more earning potential.

In the meantime, I kicked off my pvot40 blog to fulfill my writing aspirations and interview interesting people. I also started booking more trips to satisfy the travelling dream.

Things were progressing well. By early 2020, I had a better salary, tripled the number of trips and written several well received articles on my blog.

Then the COVID19 pandemic hit! ALL my plans had to stop.

The kids needed my attention with virtual school, traveling was not possible, and I was just too busy and anxious to write.

However, as the chaos of the lockdown settled, I noticed that our expenses were down drastically: no daycare, no travel plans, no dining out or even driving. In parallel, the Toronto real estate market was taking a temporary nosedive.

I realized that one way I can make money without working longer hours was to
own Real Estate!

In fall of 2020, I engaged our Real Estate agent (the best one in the city), and by January 2021 we had a beautiful condo in downtown Toronto. It was a fantastic deal – the condo was priced $100K lower than even today and we snagged a 5-year fixed mortgage rate of 1.99% thanks to my AMAZING broker.

The condo increased our household income by almost 30K a year (our expenses also increased, but in a few years the condo will be cash-flow positive while raising our borrowing powers and net-worth).

But with travel plans still mostly on hold and lockdowns continuing longer than expected, I was aching for more outdoor space that my little townhouse was sorely lacking.

A bigger house meant bigger expenses! And it led me to go for round two of
job hunts in just 3 years. I lucked out and landed a new job March of 2021, with
a substantial increase in both salary and bonuses.

Armed with my new salary, I bought a detached, mid-century house, with an
amazing outdoor space and a fully finished basement for the kids to roam
free on September 1st, 2021.

I also happen to sell my old house a few weeks after purchasing the new house and we benefitted greatly from this minor arbitrage (in a rising market) because the sale of our house exceeded ALL my wildest expectations! And we were able to use the mini windfall to establish a good emergency fund, add to the RRSP, pay off consumer debts and set aside money for future house repairs.

By the end of 2021, we were in a great place financially.

I looked at our household budget spreadsheet and the projected surplus at the end of 2022 looked better than ever before!

Yet, I was not travelling more or writing more or meeting new people. And being on a complex program, with 100+ people and executive scrutiny at work meant almost non-stop online meetings.

I was also seeing that all my additional income was likely go into buying more stuff: more expensive restaurants; Smythe instead of discount Banana Republic; luxury car instead of our 2010 RAV4.

I was happy but not 100% aligned with where I wanted to be…

Stay tuned for part III.

My Own Personal Career Pivot – Part 1

In spring, I resigned from my corporate job after 15 years to start a role in a startup.

Over the next few posts, I am going to talk about this pivot and give updates on what I am learning from this new “world”.

First a little story about my career so far.

I started my first corporate job at Bank of Montreal (BMO) in 2007 as a Senior Business Analyst with a salary of $60,000.

Money had never been a big motivator for me and in 2007 I was married, living in an adorable apartment and a respectable job that paid well was more than enough to make me happy.

BMO was a blast for me.

We were several years past the dot com crash and at the height of the bubble that eventually led to the 2008 financial crisis.

It was a fantastic time to be at a financial institution. I was part of a cohort of New Grads in Capital Markets Tech. And we were treated like the “best of the best” and we were a group of fun-loving young people – smart, ambitious, energetic with a good future.

We were unencumbered, loved life, saw corporate success as a worthwhile ambition and loved being part of the Bay Street glamour.

I am friends with many of my former BMO colleagues 15 years later. I still adore every one of them and rejoice watching them blossom into their best selves (often on LinkedIn).

The early years went by quickly amidst a haze of good times.

There were poker nights, happy hours, and club nights.

There were tacos and margaritas and deep conversations about life, career, nature of humanity.

There were inside jokes and being squished in the backseat of a cab illegally with too many people.

There was Beatles Rock Band.

It all changed when I had a baby.

At 28, I was the youngest one of my peers to have a baby. The first maternity leave was an excruciating adjustment (but I survived and eventually thrived). But when I returned from my maternity leave, everything felt different.

Most of my friends had moved on to a different role or moved into senior positions, and I was now a mom who couldn’t go anywhere.

There was already a cohort of “new grads” who saw me as a boss type – a woman in her 30s with a child and a grown-up life.

So, I left it all behind and moved to TD and joined its insurance group. I spent the next 9 years of my life there in a variety of positions.

TD gave me some wonderful friendships that I still hold dear, but I never felt that sense of community I did at BMO. (I realize with some sadness that what I experienced at BMO was a product of my age and environment and I am unlikely to get there at work ever again.)

Still, there were lunches and pubs and at least one house party where there was dancing on a kitchen countertop.

The corporate environment, especially TD, gave me an enormous sense of stability.

It allowed me to make good money (salary grew at a steady pace) while having a manageable workload as I raised my children and dealt with my father’s cancer.

TD corporate culture was polite and organized. And I am so grateful for everything I had because of it.

Even as I write this, it is obvious that much more than the work, what made my corporate career satisfying were the friendships.

So in 2018, as I approached 40, I realized I could not picture myself climbing the corporate ladder for the next 20 years of my life. I needed something more.

Thus, I kicked off a major career pivot without even realizing it…

Stay tuned for Part II

Lessons Learned from Buying an Investment Property

Mid-January I became the owner of my second ever property.

I bought a house back in 2008, a little Townhouse where I grew my family. And when I saw that our mortgage was about to finish, I thought why not get a new mortgage!

I like mortgages. They are a big pile of money a lender lends you, with a low interest rate (at least these days). In return you get an asset that increases in value and brings in some rental income!

Let me share with you my adventures in real estate and some lessons I have learned along the way.

The Whys

A very clever fellow named James Clear once Tweeted “Instead of working toward retirement, work toward your ideal lifestyle. There is usually a path to get there in a few years instead of a few decades.”

My ideal lifestyle always included a house in the Toronto Beaches neighborhood and a condo downtown.

Yet, considering how hot the downtown market has been the past decade, a downtown condo was not a realistic purchase for us. My value conscious, immigrant mind, could not justify paying $600K+ for a one bedroom in Liberty Village.

So, focus was on the house at the beaches. That was tough but achievable. We had good family incomes; we were lucky to buy the first house right before the R/E frenzy. And our most expensive years, two little ones in daycare, were behind us.

But buying a new house was not supposed to be for another few years! The kids were still in part-time daycare and we had grand plans to travel the world. I expected to move into our Beaches dream house when my older son was in high-school and that was still over 5 years away.

Then Covid happened.

Day care, vacations and travelling all became a thing of the past. We stopped going out. We stopped spending money. And with the mortgage nearly complete, an investment property seemed like a good place to funnel the savings.

Assembling the Team

Key to all successful projects (missions or heists) lies in the assembly of the team. We kicked off our investment property project by engaging a real estate agent.

I find Real Estate agents are often unusually beautiful, impeccably stylish and highly driven (shout out to my mother-in-law). And our agent, Tori Nguyen, turned out to be one of the most beautiful, stylish and driven in the city (follow her on IG)!

Tori brought a wealth of Real Estate experience to the table. She knew all about renovations, noticed details we missed and was a master at seller psychology. She was also super generous, hard working and always prepared. Attending showings, even when the city was in lockdown, was easy and painless thanks to her.

Tori was just persuasive enough to help us overcome the fear of making big decisions. She helped us by asking questions, being totally honest, moving quickly, pivoting when needed and by being available.

Second member of the project team was my brilliant friend Quyen Taylor, who is a mortgage broker. This woman knew her mortgage products inside out and without her expert advice I doubt that we would have gotten so far.

Quyen’s real estate and financing lens is unique. She came to us with financing options normally unbeknownst to a layperson.

An independent mortgage broker is helpful for all buyers but can be especially invaluable for a second property or exceptional cases.

Finally, I downloaded an awesome little app called HouseSigma to browse real estate.

HouseSigma shows the listing, provides high level market analysis and provides past listings on the property, including leases.

The user interface is delightful and easy to navigate. If you are browsing real estate in the Ontario market, I recommend this app.

The Homework

Next step in the buying process was understanding our financial current state.

Buying a house 12 years ago was so much simpler as we had no money and only two bank accounts. Now we are a mess of checking accounts, savings accounts, RRSPs and Credit Cards and digging through all of that was not fun!

On the bright side, reviewing our finances did motivate me to get my RRSPs organized, so that was a bonus!

Armed with all our financial info, Quyen was able to strategize the best way to fund our new purchase. She showed us how we can pay off our current mortgage six months earlier than expected. And how we can use a combination of our home equity line of credit and savings to manage the down payment and closing costs.

On our side we created a spreadsheet with a detailed breakdown of our income and expenses and added easy ways to evaluate the affordability and profitability of potential properties.

We set an absolute maximum budget of $750,000 based on what we could afford comfortably.

The Search

Initially it made little sense to buy an investment property that did not generate a profit. And as homes in Toronto were hella expensive, Tori suggested we look to Durham region to find a “deal”. We investigated purchasing a small detached house, turning it to a duplex and collecting two rents.

Oshawa seemed perfect. It was a developing town with a bright future. Houses were reasonably priced. It was still a short commute from Toronto. As a bonus, Tori was experienced in the rental market in Oshawa and we trusted her judgment.

However, shortly after our first evening of showings, the Oshawa market skyrocketed. Properties started selling for $200K over asking and even before renos they were already outside of the budget.

Oshawa market was too hot, and the pressure showed me that I was not ready to bet it all on Oshawa. Yes, it had good potential to make money, but the cost of buying, renovating and managing the rentals was still high. A house in Oshawa brought nothing but the possibility of a positive cashflow. And it really did not seem enough.

I was ready to wait.

But as the Oshawa market heated up, the downtown Condo market was cooling down. Inventory was piling up as people exited the city. Rental demand for small condos were dwindling with everyone working from home and sellers were ready to offload.

The more we looked at the downtown condos, the more it felt right.

Sure, it would not get us the positive cashflow that two units in Oshawa would, but it would be a step towards our ideal lifestyle. A condo at the heart of Toronto would be an investment in our future. I found it was easier to decide when the value was more than just monetary.

We narrowed our search based on a few criteria:

Close to subway
New building (under 7 years)
Low monthly maintenance
Has a parking spot, a good-sized bedroom, more than one room and a balcony.

We landed on two possibilities: first was on Richmond, few blocks east of Yonge. This condo was a bit cheaper, a bit bigger. But with no balcony and the location was still developing.

The second was on Adelaide, near John, it was a smaller unit, higher floor, more expensive but with a beautiful balcony and the most perfect location.

Now I must pause to express my love of Adelaide street.

Adelaide street, from Church to Spadina, is my downtown Toronto. Adelaide is humble and unpretentious. It does not have the edge and angst of Queen West, nor does it have the corporate coldness of King. Adelaide is full of heart, charm and innovation and merely blocks away from everything important.

Once we saw the location and the building, decision was super easy. I wanted it.

I could see myself living there happily if I were alone. And even if we made little in rent, it was worth it to own a piece of a street that I love.

The Offer & Aftermath

Sellers were asking for $689,000. With Tori’s expertise, we put in an offer, and after some minor negotiations we settled on $675,000 with condo fees of ~$480 a month.

I felt good about it.

We asked for a 4-week closing period to get everything in order. Selected First National as our lender. Engaged a lawyer and an appraiser etc. Now we are mere weeks away from getting our keys.

Making the Decision

Looking back, I basically used three questions to make my decision.

First question was Can we afford it? Not just in the best-case scenario but under some stress.

I am naturally risk averse and for me this was the most important question (may not be for everyone).

We evaluated our incomes, expenses, debt repayment and additional expenses of owning the condo. Then we ran our calculations through three possible scenarios:

1a. Can we afford it if we did NOT have a tenant for a period of time?

1b. Can we afford it if we temporarily became a one income household?

1c. Can we afford it If 1 & 2 happened at the same time?

With our primary mortgage paid off, the answer to all three question was yes but with various degrees of belt tightening.

Second question was Is the property worth the price?

We relied on Tori’s expert judgment to determine a good price for the condo. An appraisal following our purchase concurred with the price we paid.

We additionally looked at historical price of similar condos in the same building. We tried to envision the value of the amenities in a post-Covid world. We invested in features we felt were valuable, like a bigger bedroom, a giant balcony and a parking space. We chose a location that was most likely to recover quickly (compared to other downtown pockets).

Overall, we bet on the city returning to pre-Covid vibrancy eventually and that the property will appreciate.

And the final question was am I getting something beyond just money when investing in this property?

Whenever I envisioned my future, I always saw a house in the Beaches and a condo downtown. And this little condo fulfilled a part of that vision. When I think of future moments in this place, even if we rent it out for the next few years, it makes me smile.

I can see one or both of the boys living in that condo when they go to school or start their first jobs.

I can see date nights or girls nights downtown ending with cocktails at the condo.

I find myself already call the building, our building. It feels right.

Lessons Learned

In summary, here are the key lessons I learned from the process of buying a second property:

You have thousands of options available in a place like the GTA. Take time to dream about your future and explore different options. Let your imagination guide you to what is possible and eventually you’ll land on something that fits.

When ready to start the purchase process, assemble a good team first. I recommend an experienced real estate agent and a knowledgeable mortgage broker, especially for an investment property.

Know what you can afford. Spend the time to dig into your own finances and be hyper realistic about your budget. When buying real estate, going too cheap is not necessarily a good idea. But maxing out your budget can be even worse.

Be reasonable with your fears. When evaluating your worst-case scenario, try not to think of catastrophes. The only decision when faced with a catastrophe is to do nothing. Conversely, you will own this property for a few years, so account for realistic set backs.

Trust the experts to guide you. Be very selective when assembling your team of experts, but after that trust their judgment and ask for recommendations. If you feel the urge to second guess your expert, ask a lot of questions instead. It is very likely they know something you don’t.

Give yourself time and be patient. It can take months to find the right property.

But decide quickly when you find something you want. All the preparation you have done up front should help because real estate moves quickly – be decisive and stick to your criteria.

Make sure your team compliments your blind spots. I am naturally very risk averse, so I appreciated a real estate agent who was bolder. On the flipside, I knew little about the mortgage world, so Quyen’s vast knowledge of mortgage products filled me with comfort.

Aim for the best you can afford. Think in dimensions of what can you comfortably afford versus what is the best you can afford. Buying a slightly cheaper property in a shittier neighborhood or without the things you truly value is probably not that great. You get what you pay for.

Finally, buying an investment property can be exciting and fun. Try to enjoy the process and learn along the way.