You're Not Too Late. But You're Wasting Time Copying Someone Else's Move

The market will always seem crowded. You will often feel too late. If only you had left to join Palantir in 2008. Or maybe you could have gotten into Facebook in 2011. Or SpaceX in 2021.

But does living a fantasy get you any closer to your goal?

In all likelihood, not only is the first or second company you’ll end up at one you’re not thinking about as you read this, but you could easily be in a role you haven’t thought of. Even then, in the beginning, when you’re searching, you can’t control which company hires. And for those that do, you’ll have a limited impact on their overall path to being a unicorn.

That’s because the way you transfer your skills and experience will remain a work in progress. Almost an artistic approach. You’ll go through consistent, laborious reflection and reinvention.

What you can control is the system you build and the diligence you put forth. You can control whether you’re in rooms where people talk about their work. You can control whether you listen to how they actually describe what they do versus the title. You can control whether you’re talking to people before you need something from them. Luck is when opportunity meets someone who’s already paying attention.

Remember, these are efforts you must own. Don’t ever outsource this process. Having someone else do the thinking for you will always end in disappointment. That’s why you need your own path. Yes, informed by the experience and advice of others. But still always yours. Not the carbon copy of a hundred other formers. This is how you end up in a new set of cubicles doing a different version of the job you wanted to leave behind.

Owning the process involves engaging in conversations where you may not yet know what questions to ask. You run the risk of dismissing seemingly solid advice simply because it does not align with your goals, even when those goals are more about how you feel than a specific set of desired outcomes. This requires constantly living with the nagging doubt that you might be choosing the wrong paths, and accepting that progress may appear slower than simply copying someone else’s route.

Of course, copying is seductive. You’ll see plenty of other former feds, apparently satisfied and thriving, as members of a cost center at some impressive private-sector logo. As you pursue these roles, you get to tell yourself you’re being strategic, not just guessing. It’s reassuring to point to someone who appears to have succeeded and say, “I’m doing that.”

Failing to introspect often leads to optimizing for the traditional perks of government work, like job security and status, only to realize too late that the role and company matter less than your true motivations. Alternatively, you may secure a seemingly ideal position but find yourself in an organization where everything moves sluggishly, beset with politics, consensus-building, risk aversion and so on. By then, you’ve invested time and convinced yourself it’s acceptable, even claiming that first post-USG role has given you everything you ever wanted. Without reflection, you risk losing sight of your core motivation for a career transition and settling for less than you deserve.