There Is No Medium Risk

Every job is a bet. Every path is uncertain. And not betting is a bet too.

Early in your career, it’s tempting to optimize for safety. You want predictable hours, a name-brand employer, a path you can explain to your parents or that looks good on LinkedIn. But optimizing for what feels safe often leads to a pretty dangerous outcome: capped upside with real downside.

And, listen, we’re not advocating taking reckless swings or quitting your job on a whim. But it is worth asking the question: If every path involves risk, which risks are most likely to pay off big if they work?

Nail Down the Risk

Most conversations around career risk include things like:

• Leaving a stable job for a startup

• Choosing a role where you don’t meet 100% of the qualifications

• Taking on a tough challenge where you might fail publicly

But here’s what people don’t often consider:

• Spending five years in a job that doesn’t stretch you

• Building your resume instead of your skills

• Being so careful that you never become irreplaceable

• Having no upside when things go well

Those aren’t safe moves. They’re expensive ones. You’re paying in time, energy, opportunity, and long-term compounding.

Think of your early career as a series of bets. Some will fail. That’s okay. The goal is not to avoid failure – it’s to uncap your long-term upside. What you’re trying to do is understand the type, magnitude, and probability of the risk you’re taking — each of us has some risks that are bigger than others, and some that matter more than others.

Ask yourself:

• If this works, how much better does my life get?

• What skills, relationships, or reps will I gain – even if it doesn’t work?

• What’s the worst-case scenario? Can I live with it?

A smart early-career risk is one where you have limited downside, and massive potential upside – not always financially, but in terms of leverage: skills, experiences, mentors, autonomy, and credibility.

Understand the Upside

That doesn’t mean doing something “cool” or “edgy” just for the story. Nor does it mean chasing trends like crypto, creator brands, or AI just because they sound exciting.

Just like in investing, you want upside variance – not noise. You want to be in situations where your work can disproportionately impact your trajectory. Where if it goes well, it opens doors that would’ve otherwise stayed closed.

That usually means:

• Working under someone who will teach you more in 2 years than you’d learn elsewhere in 5

• Getting into a role or environment where outcomes are visible and ownership is real

• Choosing a team that’s small enough for your contributions to be evident

• Accepting a stretch role where you’re a little in over your head, but supported

• Saying no to paths that sound impressive but don’t stretch you, or roles where there’s no room to run even if you succeed.

These aren’t always easy metrics to judge, especially not immediately.

Bet Where It Matters

Every career decision has a cost. Not just in salary or title, but in what it costs you in momentum, agency, learning, and growth. How you think about risk is intimately related to how you think about the long term. At Permanent Equity, we regularly talk about the fact that there are some businesses we would have sold at various points if we had had an option to do so. While we’re committed to long-term thinking and acting, that commitment is sometimes supported by an unintentional Ulysses contract – our hands are tied against the call of a siren’s song (or the screech of a risk that looks like it’s on its way to zero in the short term).

To illustrate through another mythological reference, if you make a list of all the potential risk areas, it’s easy to feel like you’re flying too close to the sun… all the time. Equally risky is the inverse: under-appreciating the impact of one or more elements of risk.

For every decision you’re making, there’s a vast buffet of risks you’re taking. From that smorgasbord – and this is the important part – you’ve got to determine what the controlling factors are for you. What factors do you care about for success, even if everything else goes to hell, and what factors must go right for you to say a risk has paid off? And what, really, are you betting?

These are the things where you say “If we get those right, we can accept almost any other types of risk. But if we get them wrong, there’s no amount of upside that will make up for it.”

Articulating these non-negotiables – really knowing them and not underselling them – forces you to think about what it means for a risk to pay off for you and your company, even if that payoff doesn’t meet others’ definition of success (or your keep-you-up-at-night risk doesn’t meet others’ definition of risk).

Before making a decision, ask yourself:

• What am I really betting on?

• If I’m right, what do I gain?

• If I’m wrong, what do I lose?

• And am I playing a game that gets better over time?

Don’t aim for “medium risk.” It doesn’t exist.

Aim for smart risks with uncapped upside – the kind of bets that might not show up on a resume, but compound for decades.

Because if you can tilt your early moves toward learning, leverage, and long-term opportunity, you won’t just have a job. You’ll be building a career that keeps getting more interesting—and more valuable—with time.