2 min read

How to Stop Holding Yourself Back

How to Stop Holding Yourself Back
Image by Anete Lūsiņa

Getting lucky is easier than you think.

I find it remarkable how long people wait to seize the opportunities they want.

A friend recently told me that he would ask a professor for a research position if only he knew his professor better.

If this was a one-off experience, I would have simply told him to just ask and move on. But I've seen this phenomenon time and time again. It's time to fix that.

For some odd reason, people wait for permission — as if someone will drop down from the skies and tell them that they can ask for an opportunity.

Earlier this year, I started to use a new note-taking app, Napkin. I fell in love with it. At the same time, I was applying to a bunch of internships. None of them felt right.

So, I did what anyone should do: I found the founder of Napkin's email and I sent him an offer to join the team. I start in March.

The Worst-Case Scenario

It’s instinctual to fear making big asks. It’s vulnerable. Seth Godin describes this feeling in his Icarus Deception:

Our cultural instinct is to wait to get picked. To seek out the permission, authority, and safety that come from a publisher or a talk-show host or even a blogger who says, “I pick you.”

If you wait to be picked, you’ll die waiting.

The worst thing that can happen in response to making a big ask is an average-sized no.

If you want something, ask often. Send the cold email. Go up to the professor after class. Schedule a meeting with your boss.

Ask big things of big people, and great things happen.


Moonshots are called that for a reason. There’s a very good chance that your email goes unread. But, expected values require that we consider the impact of the positive. If there’s only a 1% chance someone fulfills your ask but that ask would change your career path in a direction you want — make the ask.

Serendipity can’t happen to you if you have a 0% chance of success. It happens to those with the 1%, the .1%, and the .01%.

The Games We Play

So, maybe my friend wasn’t waiting for permission. Maybe, deep down, he didn’t want that research position — he thought he wanted it since everyone else was doing it.

You only have so much time. Your big asks should align with the games you want to play.

It’s your choice. Will you choose to play status games, constantly garnering the approval of others? Or will you choose to play your own game, advancing your just cause?

You Choose How to Spend Your Downtime

Let’s take this one step further.

Don’t ask. Do.

If you have a project you’ve been pushing off, now’s the time to step up and take action. Take the first step.

You don’t need to spend your downtime cold-emailing people to get internships. You can build on your own. Build your own product, audience, brand. Hone your craft.

Or maybe it’s time to relax. You don’t need to fill every moment with a new activity just because someone else is doing it. Find your own flow. But whatever you do — don’t sit around waiting for someone to tell you that it’s ok to act.

If you want permission, this post is your permission.

Stop waiting. Start asking. Start doing.