How I think about careers
A career is the longest strategy you will ever run, and most people run it the way bad companies do: no stated aspiration, decisions made by default, course corrections only when something breaks. There's a discipline for this, personal strategic planning, and it isn't self-help with a spreadsheet. It's the same work I do with companies, applied to a single life: figure out what you're actually trying to build, get honest about your position, and then run the plan like it matters.
Start with the aspiration
Every plan starts with the question most people have never answered out loud: what are you actually aspiring to? Not what's achievable from here, what you'd build if constraints didn't vote. I ask people to take real solitude with that question, write down a vision, a purpose, the values they'd refuse to trade, and then test it on the two or three people who know them best. Not to edit it. To validate it, and to provoke what got left out.
Build the plan
Then the honest look, the same one a company gets. Inside: what resources and capabilities the aspiration requires, which you have, which you'd need to build. Outside: the environment you're operating in, the market for what you want to do, where it's heading, who else wants the same ground. From there, a roadmap: multi-year, phased, with milestones, check-ins, and the resource needs written down in advance, the certification in year two, the network that has to exist by year three. Small enough to fit on a page. Real enough to argue with.
Run it
This is where careers, like strategies, usually die, so this is where the ongoing work lives. Regular check-ins where I serve as quality assurance on the plan: are you moving, what's changed, and does the change warrant revising the plan or just your patience? New information arrives, circumstances shift, and the discipline isn't rigidity, it's deciding deliberately instead of drifting. And we mark the wins, because motivation is a resource too, and it compounds.
Start with the aspiration
✳︎
Build the plan
✳︎
Run it
✳︎
Start with the aspiration ✳︎ Build the plan ✳︎ Run it ✳︎
One thing I've learned to do early: after the first conversation or two, I ask for something substantial, usually the aspiration work itself. What comes back tells me everything. Some people want a plan handed to them in an hour; this isn't that, and I'd be wasting both our time pretending otherwise. The people this works for are the ones who do the assignment. The plan is theirs; my job is to make sure it deserves them.
My longest-running mentee started as a college senior with no idea what came next. We did exactly this work: the aspiration, the honest analysis, a phased plan, and then years of running it, internships, networking, the resume, the interviews, and the moments where new information changed the plan itself; the focus she started with isn't the one she has now, and that's the plan working, not failing. Today she's a manager at a consultancy with her MBA, and we still meet, because the strategy didn't end when the first goals fell. It just got a longer horizon.
I mentor a small number of people through this, students, former students, and professionals from my network, and the roster stays small on purpose. If the way this page describes the work sounds like the work you're ready to do, get in touch and tell me where you are.
