The dilemma
I’ve been stuck in deciding my next professional step. Do I focus on coaching and facilitation? Do I focus on trying to move closer to C-level where I can have a very hands-on impact? Or maybe project management? What about AI and data science?
I’ve seen other respected friends and colleagues with a clear idea of exactly where they want to go – why don’t I know that? How do I figure that out? I’ve spent the last six months puzzling over these questions, feeling the pressure to find the “right” path.
I’ve gotten to the point where I know I need a change. But knowing that I need a change and knowing what that change needs to be are two very different things!
The pit stop perspective
I had opportunities, but I wasn’t sure they were the right fit. Initially, I was thinking about them as pit stops – necessary but unpleasant pauses on the journey to my ultimate destination. I don’t know about you, but I’m not a fan of pit stops. Highway bathrooms tend to be awful.
This perspective left me feeling stuck and uninspired. I was waiting for the perfect opportunity, the clear path forward that would align with my imagined “main quest.” But then, something changed.
New quest available: explore a side quest
I was discussing a potential job opportunity with a colleague. While it seemed to be a good fit for my skillset, I felt unsure because it didn’t align perfectly with my long-term goals. That’s when my colleague, Jaco, offered a simple yet powerful analogy that completely shifted my thinking: “It’s like a side quest in a game.”
In video games, side quests are awesome: they tend to give flavor and nuance to the game world and can be even more interesting than the main quest. They offer opportunities for growth, unexpected rewards, and new perspectives. Of course you should pursue side quests!
Suddenly, my outlook transformed from “Ew, highway bathrooms,” to “I’m going on an adventure!”
Embracing the adventure
You can build on this metaphor further: in games, you can have multiple quests in your quest log. You don’t have to tackle them all at once – you can even choose to drop them if they’re no longer interesting or relevant.
Applying this to my career, I realized that exploring AI doesn’t mean I have to abandon my interest in facilitation. I can add both to my quest log and see where they lead. Maybe one will reveal itself as more aligned with my goals, or perhaps they’ll combine in unexpected ways.
I’m starting to think (based on all of that personal exploration, which may be a completely new blog post) that my main quest is a thirst for knowledge and new experiences. The more dots and data points I have, the better I can connect them. Who knows? Maybe what starts as a side quest will turn into the main quest of my career journey.
The power of reframing
It is incredible how a simple reframing completely shifted the way I saw my options. I went from feeling closed off, blocked, and frustrated to being curious and interested again. I’m back to being willing to jump and figure it out on the way down.
This new perspective has reignited my enthusiasm for exploring different career paths. Each opportunity now feels like a potential adventure—a chance to learn and grow—rather than a risky commitment to an uncertain future. I’ve always been curious about what lies around the next bend, and career paths offer far more intriguing twists and turns than any highway ever could.
I can’t believe I’m saying this, but maybe it really is more about the journey than the destination.
Embrace your side quests
As I set out to discover what interesting quests I can find in my professional journey, I invite you to consider your own path through this lens. What side quest have you been hesitant to pursue? How might viewing them as opportunities for adventure and growth, rather than distractions from your main path, change your approach?
Remember, in both games and careers, it’s often the unexpected detours that lead to the most rewarding experiences. So why not embrace your side quests and see where they take you?

I like the analogy! Just keep in mind that like a side quest, there can be penalties to your main quest when you take such a detour.
In my case, it was management. When you’re at my level, everyone wants to hire you as a manager and (at least for me) it suuuuuuuuucked! Taking a job and then bailing after only a few months can hurt your CV, and in my case I did this twice in a row, first with being a manager and then again at a Big Tech company as a staff engineer. The former was terrible because (as it turns out) I hate (nearly) everything about management, and in the latter case, the culture and architecture literally gave me nightmares.
So now my CV has two back-to-back 3 and 6 month side quests that will inevitably inform future options.
I don’t want to put you off side-questing, because you do learn a lot about what you want. Indeed, look what I’ve learnt from the above), but I just want you to go in with your eyes wide open.
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Thank you! I was wondering about those jobs in your history. I think the side quests need to make sense: I’m unlikely to go be a kindergarten teacher, for example.
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