learn, laugh, scale, earn

I’ve taken a lot of jobs over the years. Some were great. Some were hard. A few were both at once, which is usually when you learn the most. Looking back across almost three decades — from Microsoft to RealNetworks to Sony to BMW to a startup I founded that the pandemic killed to Placer.ai where I am now — the roles I’m most grateful for weren’t always the ones that initially looked best from the job description.

Over time I’ve developed a simple test. Four questions I ask before starting any job search or taking any role. A job worth taking should meet at least one. Ideally more. If it meets none of them, that’s important information too.

If you take the job, are you learning?

The job is teaching you something genuinely new — a new skill, a new industry, a new way of thinking about problems. Early in a career this happens almost automatically. Later on you have to look for it more deliberately, because the default tendency is to gravitate toward roles that confirm what you already know. People will hire you exactly for the skills you bring to the table. That’s comfortable, and comfortable is often a warning sign.

Microsoft was this for me before anything else on the list. I arrived there early enough that the company still felt like it was inventing something — not yet the juggernaut it would become, not yet running on its own gravity. There was no MS Office, no Exchange server, and Windows was just gaining market traction. What I learned there wasn’t a skill set as much as a posture: what it looks like when a platform company is executing at full speed, and what it costs to be inside that when the speed is the point. It set the baseline for everything that came after.

Going further back: joining RealNetworks in 1998 was the same kind of bet. Streaming media was still an experiment. Broadband wasn’t ubiquitous and we didn’t know yet if people would consume video and audio on their computers via their limited connections, let alone pay for it. We figured it out as we went, building the first streaming subscription service alongside a platform that eventually reached 300 million users worldwide. It taught me more than any classroom could have.

My time at INRIX fits this one cleanly too. I came in to lead product and marketing for a machine learning company at the intersection of connected car data, automotive OEMs, and smart city infrastructure — an industry I’d been adjacent to but hadn’t operated in deeply. It was a steep learning curve. I loved it. And the role it unlocked next — founding ReachNow as BMW’s North American mobility startup — I probably couldn’t have landed without it. Learning compounds.

Is this the job that keeps you laughing?

The team is genuinely good. The culture is one where you can do your best work without leaving too much of yourself at the door. This criterion is easy to undervalue when evaluating an offer — compensation is concrete, culture is a vibe — but I’ve come to believe it matters more than almost anything else over a long engagement.

I think about Screenlife Games, where I ran the team making Scene It? trivia games based on Harry Potter, Star Trek, and Twilight. (I have opinions about which of those three is the superior franchise. I’m also right.) It wasn’t the highest-profile role or the biggest team within Paramount. But the team was creative, the work was genuinely fun, and you got to know people were having fun playing with the products you built.

I remember a product review where we were playtesting and someone kept getting tripped up on the same question and the whole meeting just dissolved into people trying to out-trivia each other for the next twenty minutes. That wasn’t work. We were just fully in it. That’s what the laughing criterion actually means in practice. You can’t fake a room like that. And when you’ve been in one, you notice immediately when the next one isn’t.

The laughing criterion isn’t about a workplace that throws ping pong tables at retention problems. It’s about finding people you respect, working on something you believe in, and feeling like the effort is worth making together. When that’s present, hard becomes manageable. When it’s absent, even easy becomes a grind.

Are you scaling to something bigger?

The role is expanding what you’re capable of — as an operator, as a leader, as a person. This isn’t just about title progression. It’s about being handed a larger stage than you’ve stood on before and figuring out how to fill it.

ReachNow was this for me. BMW brought me in to help found and run their North American mobility company — car sharing, ride hailing, and long-term rental from a single app, across three cities, from scratch. I’d led business units before but never built something zero to one inside a global automotive company while trying to operate with startup speed. We grew to over 100,000 members and nearly $20 million in revenue. The merger with Daimler that followed returned 5x on BMW’s investment. None of that would have happened if I’d stayed in a lane I already knew.

Scaling doesn’t always mean running a bigger team or a bigger P&L, though it can mean both. Sometimes it means taking on a problem you genuinely don’t know how to solve yet. That discomfort is usually the point and the fun.

Are you earning what you’re worth?

Sometimes the role is financially compelling enough that even if the other three criteria are harder to find, the long-term value — in salary, in equity, in the options it opens up — is reason enough to say yes. I want to be direct about this one, because people in tech have a habit of pretending compensation isn’t a primary consideration when it almost always is. Acknowledging that isn’t crass. Pretending otherwise usually costs you later.

I’ve had “big-company” jobs where the cash compensation was amazing but the bureaucracy was stifling. I’ve worked in startups where there was freedom to innovate and the promise of a big payday at some future liquidity event that never happened. And sometimes you take a job — or stay in one — for exactly this reason alone: the money is just too good, or the risk of not finding comparable compensation elsewhere is too high. I get it. We all have to eat. Just keep asking yourself whether the money is worth missing out on the chance to learn, laugh, or scale if those aren’t also present.

At least one. Ideally more.

The roles I remember most — the ones that made me better, that I’d take again knowing what I know — almost always checked at least two boxes. Learning and scaling tend to come together naturally. Laughing and scaling can coexist when culture is built with intention rather than left to chance. Earning alone, without any of the others, works for a while until it doesn’t. Money is a band-aid, not a cure.

What I can tell you is that the framework holds up across thirty years of looking back at it. I know which box I was checking at each step, and I know which ones I’m not willing to skip the next time around. The criteria don’t decide anything for you. They just keep the decision honest. And when something genuinely checks all four, you usually don’t need the framework at all. You already know.