How do nineteen months fly by so quickly? In some ways it feels like just yesterday that I made the difficult decision to leave my old role and, after over twenty long and fruitful years with my first and only real professional role, simply stop for a while.

In the over year and a half that followed, the world around me changed dramatically. The AI hype cycle truly took off with an investment bubble that has seen untold billions sunk into startups, large established players, and the picks-and-shovels companies that underpin the industry. In parallel, we saw increasing evidence of a white collar recession taking shape, with the software industry no exception. While I don’t personally believe the former trend has played much of a part in the latter, these parallel trends have seen the software industry disrupted in a way it hasn’t been since the dot-com crash of 2000.

Meanwhile, the political landscape has been utterly transformed. As the alt-right continued to rise and eventually take power in our neighbour to the south, we’ve seen sustained pushback against diversity, equity, and inclusion (DEI) policies and practices, and a decline in support for investing that takes into account environmental, social, and governance (ESG) factors, with some of that pushback taking the form of real changes to the legal and regulatory landscape in the US.

As if that weren’t enough, in the first quarter of 2025 we’ve seen a sustained attack on Canadian sovereignty, as the new American administration has begun to wage an economic war on this country while cozying up to strongman dictators across the globe.

I genuinely don’t remember the last time the world felt this… precarious.

As you can imagine, given this context, I was more than a little anxious about beginning the hunt for a new job.

So imagine my surprise, back in late November, when a former colleague reached out after noticing I was open to work…

Back in August of 2024 I wrote a little retrospective blog post about the first year of my break, the state of the tech industry, and what I’d love to find in a new prospective employer:

Well, as I look at my future, I am certain of one thing: with at least fifteen to twenty years still remaining in my career, whatever I do, it must be in service of building and creating and raising up those around me rather than simply making ends meet and enriching myself.

I went on to say that:

At minimum that means a change of industry. Whether it’s something like healthcare, or elder care, or education, I truly believe technology still has enormous potential to have a positive impact, so long as those wielding that technology focus on building and supporting people and communities and not simply lining their own pockets.

Unfortunately, given the shifts in the broader industry, these words were feeling increasingly unrealistic. After all, with the alt-right ascendant and the job market thinning out, it felt less and less likely that I’d easily find a position in a company with values that closely aligned with my own. Compromise seemed inevitable.

As the summer turned into fall, I started to make some token efforts to get the job search started. I attended various events during Edmonton Startup Week, which was a lot of fun and a great way to build out some connections here in the city. I did a bit of work to polish up my resume and (to a lesser extent) my LinkedIn profile. And, of course, I started trawling through job postings on LI to get a feel for the types of roles I might want to explore.

But, if I’m being truly honest with myself, I really wasn’t putting in the kind of effort required to land something in the prevailing job market, especially given the rise of ghost jobs and the AI-powered arms race that’s made both applying and recruiting for jobs an absolute nightmare.

Amidst all this, in early October, I decided to reach out to a mentor, former manager and colleague, and old friend of mine, Mr. Dan Wilson. As a general rule, I’m pretty bad at keeping in touch with folks, and Dan is no exception. Over the break we’d had coffee a half dozen times, and I realized it was about time we caught up once again. As always, the conversation meandered, but the topic of the impending job hunt came up and I talked a bit about what I was looking for in a new position. At the time I didn’t think much of it, other than that Dan might have a little advice for an under-motivated job seeker.

Then, in late November, I got a message from Dean Bittner, current CTO of RUNWITHIT Synthetics and another former manager and colleague from my old INVIDI days, enquiring about my open-for-work status and if I’d be interested in a conversation. And of course I said yes, if only because, many years ago, I set a rule for myself that if anyone opens a door for me, I’d walk through it, just to see what was on the other side.

I wouldn’t find out until much later that Dan is the one that suggested to Dean that it might be worth reaching out.

That first call went well, with both of us believing it was worth continuing the converation, but then, I suspect due to interruptions around Christmas, the lead went cold.

Finally, in early January, I decided to reach out again and see if I could get the conversation restarted, and that’s when things really started moving ahead in earnest.

As the conversations with RWI started to heat up, I decided to do what I often do with a new lead: e-stalk the company.

Fortunately, with resources like LinkedIn and so forth, you can learn a great deal about a prospective employer before ever walking through the door, and so I spent a fair bit of time trawling through RWI’s website, current and former staff LinkedIn profiles, and so forth.

And the more I learned the more interested I became.

RWI has found a niche doing synthetic data generation, modeling, and forecasting for human populations in their lived environments. Or, to put it in more familiar terms, think SimCity but a lot more sophisticated.

Using this technology, RWI was able to, for example, model the human impacts of a major power outage during a cold snap in the Nashville area, including identifying at-risk populations who simultaneously lacked the necessary social infrastructure that would support them through such an event. Similarly, RWI runs the REAL Edmonton Regional Lab, where RWI brings together stakeholders in the city and uses its technology to answer real and pressing questions impacting the capital region, most recently by modeling the impacts of impending caps to the number of international students entering Canada.

These projects are just a couple of examples of RWIs overall business, which is to put tools and data in the hands of decision makers who are trying to create, as they put it, “resilient, equitable, and sustainable futures.”

And so I found that, as I learned more and more about RWI, the more I felt that this was a company that also “[believed that] technology still has enormous potential to have a positive impact, so long as those wielding that technology focus on building and supporting people and communities.”

On top of that, it seemed to be the case that RWI didn’t just believe in the values of diversity, equity, and inclusion–values that, in my opinion, have never been more important–but lived those values every day, and expressed them through their products and services. In a corporate world that seemed to be increasingly rejecting these values, RWI seemed to be a shining example of a group embracing them.

As if that weren’t enough, RWI was also small. While INVIDI wasn’t huge by the time I left, it was big enough that I found it increasingly difficult to enact positive change in a meaningful way. Big ships are just much harder to steer. So I knew that, wherever I landed, my preference was for a smaller company, and at just twenty to thirty employees, RWI sounded just right to me.

And finally, as the cherry on top, RWI is also a remote-first company. While I had resigned myself to the possibility of having to return to an in-office position, a hybrid or remote arrangement was definitely preferable to me, and somehow RWI managed to tick that box as well.1

After that second call with Dean in early January, I had a follow-up chat with a number of their more senior leads that, I thought, went very well (and left me quite impressed with the group). They were then kind enough to invite both Lenore and I to their Q1 2025 REAL event where I got to see their team in action as they presented results to their stakeholder group and facilitated some fascinating conversations around the topic of Canada’s international student population. Then, finally, I was able to chat with Krista, their head of HR (who was on the previous group call but never managed to get a word in edgewise…), where it became increasingly clear that we shared a lot of the same values regarding staffing, team building, organizational culture, and so on.

At this point, I was feeling the strangest combination of both confidence–that I’d be invited to join the team over and RWI–and nervousness–that I’d completely misread the situation and that I’d have to turn back to searching for a job in earnest.

I was also surprised to discover just how ready I was to start something new. Instead of mourning for the end of this career break, I found myself more and more bored and I looked forward to starting a new challenge. It seems the timing really was right.

Fortunately, my confidence was well founded, and in early February I received a formal offer of employment. It was official, I was going to be taking on a product role at RWI!

As those conversations turned toward the shape of a job offer, I made one unusual request: at the suggestion of a friend who also took a (much shorter) break for personal reasons and then went through the challenges of going back to work, I asked if it would be possible to arrange a gradual start, working 50% time in the first week and 75% time in the second, as a way to build the mental stamina I knew I’d need to make it through a full day.

And, to my great fortune, RWI found a way to make this work.

And man, I can tell you, I am very grateful. Having onboarded many staff over the years, I know how mentally taxing starting a new role can be, but that’s doubly true if you haven’t worked in a while.

This post is actually being written after my first week at RWI, and so far I can say those early impressions during those interviews and at the REAL event have born out.

I particularly enjoyed two things during the week. The first was a chat on Tuesday with some of the leadership group as I tried to get a handle on the shape of the current and future business. During the conversation I was truly impressed by how open and transparent everyone was. Coming from a company where getting basic financial information about the business outside of extremely structured quarterly updates felt like pulling teeth, RWI’s approach was truly refreshing.

The second event was on Friday morning, when the technical staff hold their “Win Day” meeting, during which each person on the team shares and celebrates some win from the week. As a team building exercise, it really was delightful, but more importantly: they’re small enough that they can just get the entire technical team together on a call to pump each other up and find joy together! I hadn’t realized how much I missed that.

Otherwise the week was characterized by four major threads of activity: getting through the usual onboarding tasks (filling out forms, completing trainings, etc); having conversations with senior stakeholders to get their perspectives on the business and my role in it; coming to grips with the current business practices, products, technology, and gaining some sense of where things are headed; and digesting, synthesizing, and writing down everything I was learning as part of my process of building a mental model for RWI as a company.

It was… a lot!

Fortunately, in the early part of the week, Krista was kind enough to gently remind me to leave after my half day was done2, as the temptation to keep going was difficult to resist given how much is in front of me. Yet, even working at just 50% capacity, I found myself quite tired by Friday. Work, man. It really is a lot of work.

And in addition to having to rebuild my mental stamina, I was surprised to discover I’ve also lost some of my ability to compartmentalize, which meant I spent much of Saturday morning involuntarily thinking about work. I expect I’ll have to consciously practice rebuilding that skill, as it really is critical to maintaining a good work-life balance.

Now, you’ll notice I haven’t mentioned much about what the actual role is, and to some extent that’s because I think these early days are a process of figuring that out. While the job description in the offer describes a classic senior Product Manager role, it’s not yet clear what that means in practice, today, versus, say, a year from now, in part because RWI itself has entered a real inflection point in their business, with my role being part of their response to navigating through that. As a result, it was well understood even in our earliest conversations that what I came in to do might differ wildly from what I end up doing. Fortunately, this ain’t my first rodeo in a startup, and learning and adapting as the needs of the business change is part of the fun of small company life.

Of course, I will miss the enormous amount of free time that the career break afforded me. After all, it’s already Sunday, and I barely feel like I’ve had a chance to take a breath. And I don’t look forward to threading cycling training, household chores, and all those other tasks of daily living around a full-time work schedule.

But the time has come. I’m genuinely surprised and deeply grateful that it came so naturally and easily.

  1. Though it’s worth noting that for the first 3-4 weeks I made the decision to go into the office full time as part of trying to rebuild my work routine, after which I’ll find some hybrid schedule that works. ↩

  2. Which is just another little demonstration of the way they value their people. ↩