Annual review 2023 - 3) Career

This post is part of my annual review process for 2023. This year, I’ve committing to writing a more comprehensive review, but to do so I’ve structured myself into particular areas that I think are important to cover.

To read more,

  1. Intro
  2. Best of and memories
  3. Career
  4. Relationships
  5. Health
  6. Personal growth


2023 was an uncertain year for me professionally. On most traditional metrics, it was likely a resounding success. I delivered my projects, the clients were happy and I am well liked within my company.

At the same time, I had a bit of existential crisis, was told that I didn’t belong at the company, would never make VP and sort employment elsewhere - ultimately ending with better paying job offers, that I turned down.

The year of efficiency

Net, net, I feel like I’m in a better place than I was last year. At least in terms of headspace, even if not tangibly much further along.

And I believe that was the crux of the problem. I’ve reached an inflection point in my career, where no longer is growth attached to a rocket ship. Instead, things have shifted to more of a refinement process phase. I think this is reflective of myself personally in my journey, the journey of the company but also of the wider economy.

To take those in reverse order. Funding for early stage tech ventures practically evaporated overnight, as venture capital looked decidedly unprofitable in the face of rising interest rates. Meanwhile big tech embraced the year of efficiency by laying off tens of thousands of employees. All in all, it hasn’t been a full-blown tech winter, but we’re far from the boom of a few years ago.

My company too, has reached an inflection point where everything is slowing down, to focus on efficiencies and processes. Ultimately, this is the preparatory stage that is required for the next round of explosive growth in a few years time.


Personally, I’ve been flirting with tech leadership and management off and on for what feels like at least 5 years. This was recognized with a promotion last year to a position that most would consider an Engineering Manager (but all orgs call things slightly differently). That was very nice and all but it felt like a stepping stone to the Director title.

My performance review this year decided to not give me the title this year, instead telling me that I needed to smooth off some of those rough edges. At the time, I felt slighted, like a personal attack had cost me my chance.

Bitter, I looked at those around me and tried to tear them down rather than focus on what I could be doing differently.

Now, I’m more philosophical about it. I realize that had I got the title, then or now, the day to day of the job wouldn’t have actually changed I’d still be doing the same thing, with the same folks, the only thing what would have changed is the amount of ego I had as I strutted around. And let’s be honest I’ve got enough ego to spare.


So what did go well? Fundamentally, the biggest, most tangible win of the year has to be the delivery of an AI solution for promotion pricing to one of Canada’s largest supermarkets. Objectively, within the first few months, our solution was returning something to the tune of $20 million dollars of profit via smarter pricing and reducing waste. It’s pretty hard to deny those numbers. Most projects from the big-boy consulting firms will get green-lit if they see a return-of-investment over 3 years. In fact, a 5 year ROI would be enough to get a project started, just with a couple of difficult questions. We returned the investment in under 4 months. If that’s not a resounding success, I don’t know what is.

A client happy, with noises to the affect of wanting us to hang around is a great success. Heck! A solution they keep using after we leave is a success.

Of course, what everyone forgets is that back in October, there were very real conversations taking place on our side about whether we even thought the project was possible and perhaps we should cut our losses and admit we couldn’t do it. At least that way, we would at least maintain credibility with the client.

Earlier in the year, I was a little worried that my reputation might be outpacing me and become my own undoing. To pull off a miracle once, is lucky. To pull off a second miracle is shocking. But a third miracle is just flat out implausible almost to the point of guaranteed failure.


However, when I reflect back upon the year, the thing of which I’m most proud is the mentoring. Whilst not part of my official job description or responsibilities I’ve found myself spending a lot of time in bringing up the generation behind me.

I remember how hard it was for me when I first took over a team. I did so in an environment where I didn’t have any mentoring, or even any role models to try and copy. No, I spent the early days of my leadership journey frantically reading books, HBR articles and 2x listening through the Manager Tools podcast. And despite all that extra curricula work, it was still a bumpy ride, with a lot of mistakes and unforced errors.

The best I can say, is that it was humbling. It was a struggle, and a reality check, but I’m too stubborn and proud to fail, so I made it work.

Now the tables have turned somewhat, and I find myself in a position where I can see the next of young leaders starting to take their first steps. In my own way, I’m trying to be the support structure for them that I wish I had when I started my own journey.

Am I perfect? Hardly. Will they still make mistakes? Certainly.

But if I can shortcut some of the learnings. Reduce some of the pain. Guide them around some of the more obvious traps, then I think that it will be time well spent.

That’s not to say that I don’t find it fun either. My nature tendencies towards gossip and wanting to be involved in everything are nicely rewarded with coffeeshop trips and an occasional lunchtime beer. Just recently, of the one day a week that I find myself in the office, I’m rarely having lunch outside of the context of an intimate one-on-one.

My mentoring isn’t limited to new team leads either. I’m growing an increasing pool of mid and junior level mentees with infrequent but meaningful depth. Some of these were direct referrals at one point or another, some are former team members that I’ve never really lost, and some I’ve just collected along the way.

I can honestly say, that it is these conversations that keep me at the company.