The Uncomfortable Work
on acting on your big dreams and ambition
I‘ve been thinking about this a lot lately: how easy it is to be ambitious and completely stationary at the same time.
It’s not laziness, but it can feel like it… The specific experience of knowing exactly what you want, being genuinely motivated to get there, and still somehow not doing the things that would actually move you forward. You stay busy, you stay engaged but you just don’t move.
I still think about it honestly. Having a plan and working a plan are two very different things, and the gap between them is where most of us quietly live for longer than we'd like to admit. I don't think I'm alone in that, which is partly why I wanted to write this.
So this is me trying to figure out, practically, what actually gets you unstuck.
The readiness trap
The problem with waiting to feel ready is that readiness usually only shows up after you’ve already started. You don’t feel ready for a senior role and then apply. You apply slightly before you feel ready, and then you rise to meet it, or you don’t, but either way you learn something real.
The feeling follows the action. Waiting for it to arrive first is, in most cases, just a stall dressed up as patience.
I think we conflate readiness with competence, and they’re not the same thing. Competence is measurable: you either have the skill or you don’t. Readiness is mostly a feeling, and feelings are unreliable indicators of what you’re actually capable of. Most people I’ve seen make significant career moves did so while feeling underprepared. The ones who waited until they felt ready often found that someone else had already taken the seat.
There’s also a version of this that’s more insidious, where waiting becomes a comfortable identity. You’re the ambitious one, the one with the plan, the one who’s going to make a move soon. “Soon” does a lot of work in that sentence. It keeps the dream alive without requiring you to actually risk anything. I’ve caught myself doing this more times than I’d like to admit.
Getting specific enough to be honest with yourself
What I’ve found more useful than asking “am I ready?” is just getting specific about what I actually want. Not in an abstract sense, not “I want to grow” or “I want more strategic work” or “I want to do something meaningful,” but concrete enough that I could tell someone else and they’d know exactly what to look out for.
There’s something about naming it specifically that forces you to take it seriously. Vague ambition is comfortable precisely because it’s unfalsifiable.
You can’t fail at something you haven’t committed to. But the moment you say something concrete, a specific role, a specific type of company, a specific outcome within a specific timeframe, suddenly there are things you’d need to do, gaps you’d need to close, uncomfortable conversations you’d need to have. It gets real fast. That’s the point.
A useful test: if you wrote down your career goal and showed it to someone tomorrow, would they know what to do with it? Would they be able to come back to you in six months and assess whether you’re on track? If the answer is no, it’s not specific enough yet.
The gap audit nobody wants to do
Once you have something specific, the next honest step is figuring out the gap between where you are and what the thing actually requires. This is the part people most often skip, because the answer is usually uncomfortable. But it’s just information, and it’s the only information that actually matters.
Pull up job descriptions for the role you want. Not to apply right now, just to read them honestly, like a checklist. Where do you have real evidence: shipped work, real decisions, outcomes you can speak to? Where are you papering over gaps with good intentions and future potential? Be honest about the difference.
Better still: talk to people who already have the job. Not to network, not to impress them, just to understand what the day-to-day actually looks like, what it cost them to get there, and what they wish they’d done differently. Most people are more generous with this kind of conversation than you’d expect. And the picture you get from a real person is almost always more useful than any job description or career framework.
The gap audit isn’t meant to be discouraging. It’s meant to replace “I need more experience,” which is vague and endless, with “I need to do X, Y, and Z specifically,” which is actionable and finite. That’s a much better place to work from.
Shrinking it down to what you can actually do
An 18-month goal is real, but it has no gravity day-to-day. The only thing that has actual gravity is what you do this week. So the practice, and it is a practice, is working backwards until you have something small enough to act on: one meaningful milestone for the next 90 days, one thing to focus on this month, and one protected block of time this week that you treat with the same seriousness as a meeting with your CEO.
The failure mode here is overcomplicating the system. A complicated goal-tracking setup with colour-coded spreadsheets and quarterly OKRs is, for most people, just another form of productive procrastination. The simpler you can make it, the harder it is to avoid. One thing at a time. This week, then next week.
It’s also worth saying: some weeks you won’t do the thing. Life gets in the way, work gets overwhelming, you lose momentum. The goal isn’t perfection. It’s returning to it quickly when you drift. The people who make consistent progress aren’t the ones who never fall off track, they’re the ones who notice quickly when they have and course-correct without making it a whole identity crisis.
Saying what you want out loud
This is the one I’ve seen make the biggest difference, and the one people are most reluctant to do. Tell the people around you what you’re working toward. Your manager, a mentor, a peer who’s a few steps ahead, not everyone, but the people whose support would actually matter.
Most people keep their ambitions private because saying them out loud makes them real, and real things can fail. There’s a kind of safety in keeping it internal. But there’s also a cost: the people who could actually help you don’t know how. Your manager can’t advocate for you in rooms you’re not in if they don’t know what you want. Your network can’t open doors for a destination you’ve never mentioned.
You don’t need to make it a formal declaration. Something simple and direct works fine: “I’m trying to move toward X over the next year. If you come across anything that might be relevant, I’d love to hear about it.” That’s enough.
People are generally more helpful than you expect when they actually understand what you’re trying to do. Some will remember and come back to you months later. A few will make introductions that genuinely change the trajectory. None of that happens if you stay quiet.
The uncomfortable work is the actual work
The last thing, and the one I find personally the hardest, is that the work that actually moves you is almost always the work you’re most tempted to put off. The project that’s a genuine stretch. The feedback conversation you’ve been scheduling and rescheduling. The room where you’re clearly not the most senior person and you have to earn your place rather than coast on it.
None of it is comfortable. I don’t think there’s a way to make it comfortable. The reframe that’s worked for me is treating discomfort as a signal rather than a warning, a sign that you’re operating at the edge of what you currently know, which is exactly where growth happens.
If most of your week feels familiar and manageable, your daily work and your long-term ambition probably aren’t aligned.
That doesn’t mean every week needs to be a crisis. It means noticing when you’re chronically comfortable and asking yourself whether the version of you who achieves your goal would be doing something differently right now.
Here’s what I genuinely believe: most people reading this already have everything they need to take the next step. The capability is there. The ideas are there. What’s usually missing is just the decision to stop treating ambition as something that will activate on its own when the timing is right.
The version of you that’s six months into actually moving toward something is going to look back at right now as the obvious moment it all clicked.
Start this week. Even something small. Especially something small.