Latest / Job Hopping with Fexingo: Tenure, Loyalty, and the Modern Career Resume / Why Job Hoppers Should Write Career Investment Memos
Transcript
- Lucas: Luna, I want to pitch you a career tool that sounds a little finance-bro at first, but I think it's genuinely useful for job hoppers. It's writing investment memos about your own career moves. Luna: Investment memos — like the documents venture capitalists write before they put money into a startup? Lucas: Exactly. VCs don't just write checks on instinct. They sit down, articulate the thesis, list the risks, define the exit scenarios. Most of us leap between jobs without any of that structure. We rely on gut feel, salary bumps, or recruiter persuasion. A career investment memo forces you to treat yourself as the portfolio manager. Luna: I love the analogy. But is it practical for someone who changes jobs every eighteen months? That's a lot of memos. Lucas: It's not a long document. I'm talking maybe a page, tops. The real value is the mental discipline. You write it before you take the job, then you revisit it six months in and again when you leave. You compare your thesis against reality. That's where the learning happens. Luna: So it's like a pre-mortem mixed with a post-mortem. I can see that cutting through a lot of hindsight bias. Lucas: That's exactly the insight. Charlie Munger talked about the power of inversion and mental models. One of the most dangerous biases in career hopping is the 'narrative fallacy' — we construct a story after the fact that makes our choices look inevitable and smart. A written memo from before you took the job is your best defense against that. Luna: Let me guess — you've actually done this. What did your last memo look like? Lucas: I wrote one two years ago when I moved from a large media company to a smaller startup. My thesis was that I'd gain hands-on experience building a podcast network from scratch, which would accelerate my skill development faster than staying in a structured role. I listed risks: smaller salary, less brand cachet, potential instability. I set a two-year exit horizon. Luna: And did the thesis hold? Lucas: Partially. The skill acceleration was real — I learned production, distribution, and analytics in ways I never would have at the big company. But I underestimated the emotional weight of losing institutional support. No HR, no legal, no marketing team. That wasn't on my risk list. The memo helped me see the gap between my expectation and reality, and that reframed the whole experience from a mistake into data. Luna: So you're saying the memo is less about predicting the future and more about calibrating your own decision-making. Lucas: Exactly. And that's especially critical for job hoppers, because we make more career decisions per decade than the average worker. Each decision is a data point. But without a memo, you're relying on memory, which is famously unreliable. Confirmation bias smooths over the rough edges. Luna: I want to push back on one thing though. A lot of career advice tells us to keep a 'brag document' — a list of accomplishments for performance reviews. How is your memo different? Lucas: A brag document is backward-looking and self-promotional. It's about polishing your story for an external audience. An investment memo is forward-looking and analytical. It's for your eyes only. You're supposed to be honest about doubts and weaknesses. In fact, the more critical you are, the more useful the memo is. Luna: That's a key distinction. A brag document makes you feel good. A memo makes you think. But let's talk about structure. What should a job hopper actually write down? Lucas: I'd suggest four sections. First, the thesis — why this move makes sense for your career arc. Be specific: 'I want to move from operational marketing to brand strategy, and this role gives me direct ownership of a product launch.' Second, the risks — list at least three things that could go wrong. Third, the milestones — what would you need to see at six months to feel the thesis is on track. Fourth, the exit criteria — under what conditions would you leave earlier than planned. Luna: That exit criteria section is brutal. Are people actually honest about that when they're excited about a new offer? Lucas: That's the hardest part. When you're in the honeymoon phase of an offer, you don't want to think about failure. But the best investors do exactly that. They write down the scenario that would cause them to sell. It's called the 'buy case and the sell case.' If you can't articulate the sell case, you haven't done the work. Luna: Give me an example of a sell case for a typical job hop. Lucas: Sure. Say you're moving to a startup as a senior individual contributor. Your sell case might be: 'If the company doesn't hit its Series A within eighteen months, or if my manager leaves within the first quarter, I'll start looking. The thesis depends on stability and funding trajectory.' That's specific. It's not just 'if I'm unhappy.' It's a trigger. Luna: I can see that being really grounding when things start to wobble. It removes the emotional panic because you already have a plan. Lucas: Exactly. And when you do leave, you go back to the memo and compare. Did the thesis change? Did a risk you didn't see emerge? That's where real career intelligence builds. Over three or four moves, you start to see patterns in your own decision-making. You learn, for instance, that you systematically underestimate cultural fit or overestimate the value of a title change. Luna: That's powerful. But I wonder — does this work for people who are job hopping out of necessity, not strategy? Like someone who's been laid off and needs a paycheck quickly? Lucas: In that situation, the memo might be shorter, but it's still useful. You can write: 'Thesis: I need income within six weeks. I'm taking this role because it pays the bills and buys me time. Risk: the role may not build my skills. Milestone: within three months, I'll assess whether I can grow here or need to keep looking. Exit criteria: if I find a role aligned with my long-term goals, I'll leave even if it's been only six months.' That honesty prevents you from getting trapped in a job that's just a lifeline. Luna: I like that. It gives permission to treat the job as a temporary stop rather than feeling guilty about leaving quickly. And that's especially relevant for frequent movers. Lucas: One more layer — you can also write a memo when you decide NOT to take a job. That's actually really informative. Why did you pass? Was it the money, the culture, the commute? Over time, you build a personal investment philosophy. You start to see what you truly value in a role. Luna: That's a great idea. A 'deal book' of declined offers. I can imagine looking back at those and seeing how your priorities shifted as you gained experience. Lucas: Right. And speaking of priorities — this show stays ad-free and listener-supported. A small group of listeners already chips in monthly at buy me a coffee dot com slash fexingo, and that's what keeps us making deep dives like this. If the show's helped you think through a career move, no pressure, but that's the engine. Luna: Yeah, it's a good model. Clean, no interruptions. And it lets us go into the weeds on tools like investment memos without having to squeeze in a commercial break. Lucas: Exactly. So back to the memo — I think the hardest part is actually sitting down to write it. Most of us would rather scroll LinkedIn or daydream about the new job than do the analytical work. But that's exactly why it's valuable. The friction is the point. Luna: I want to try this on my next move. What format do you recommend? A physical notebook? A digital doc? Lucas: I use a plain text file in a folder called 'career memos.' Date-stamped. No fancy templates. The simpler, the better. You want to reduce the barrier to actually writing. A Google Doc works fine. The key is that it's searchable and you can revisit it years later. Luna: What about privacy? Some people might be paranoid about putting their job search thoughts in writing. Lucas: Fair concern. If you're worried, use a local file, not a cloud service. Or write it by hand. The important thing is that you're honest with yourself. If you're sanitizing it for an audience, you've defeated the purpose. Luna: So the memo is a tool for self-accountability, not performance. I think that's the core insight. It's easy to rationalize a bad move after the fact. The memo locks in your thinking when it's fresh. Lucas: And that's why it's especially powerful for job hoppers. We make more moves, so we have more data points. But we also face more cognitive biases because each decision is emotionally charged. A disciplined memo practice turns those moves into a learning system rather than a blur of transitions. Luna: Alright, I'm sold. I'm going to write a memo for my next move, even if it's just a hypothetical one to practice. And I'll report back. Lucas: Do it. And if listeners try it, they might find that one page of honest writing changes how they see their entire career trajectory. It's a small habit with compounding returns. Luna: Speaking of compounding — that's a good note to end on. Thanks for bringing this one in, Lucas. Lucas: Always a pleasure. See you next time.