If you have ever tried to cross the street with me at a non-designated crosswalk, you’ll know that I really hate breaking the rules - especially when it comes to safety.

I’m so safe that I will wear my bike helmet in the car on the way to mountain biking.
I’m so safe that as an adult, I will wear my lifejacket in a boat and while on land within 100 meters of water. I have a reflective safety jacket in my trunk in case of emergencies.

Unfortunately, this comfort zone I’ve created has been getting a little too safe and comfortable. I’m an entrepreneur and this means that in order to grow, I have to take risks. I have to try things that might not work, and deal with the consequences of getting rejected or failing.

So I set myself a challenge.
I had to get five rejections in a month.
Five clear “no’s.” Five moments where I asked for something and didn’t get it.

Shockingly, out of 20 attempts, I managed to get… three rejections.

I showed up early to an appointment and asked, very casually, if there was any chance I could be seen sooner. Insane, right? They looked at the schedule… and took me early.

I asked someone for a networking call who I genuinely thought was out of my league. I assumed I’d either be ignored or declined. They said yes.

That was the pattern over and over again. The things I was most convinced would fail… didn’t. And the few things that did get rejected? They weren’t nearly as bad as I’d built them up to be in my head.

Now, am I sharing my actual rejections here?
Absolutely not - I am not quite that emotionally evolved.

It turns out this discomfort around failure is very human.

Psychology research shows that many of us grow up with a fixed mindset - the idea that being good at something means it should come easily, and struggling means you’re not cut out for it. In that framework, failure feels personal. Embarrassing. Like proof that you shouldn’t have tried in the first place.

But people who adopt a growth mindset (who see skills as learnable) experience failure differently. To them, failure isn’t an identity statement. It’s feedback.

There’s also a growing practice in academic and professional circles called a “Failure Resume” which is a document where people track rejections, missed opportunities, and things that didn’t work.

When you actually write these things down, you start to see something important:

Everyone who’s doing interesting work has a long list of things that didn’t pan out.
(We just usually don’t see that list.)

Now, if you’re doing a “Failure Resume” as a solo activity it can be soul-crushingly depressing.
Cut to me, in a dark room, listing all my failures and rejections in an excel sheet and listening to my “Sad Girl Indie” playlist.

This is why I recommend sharing this document and doing this exercise with a buddy.
The other person can help cheer you on and hype you up when you’re asking for something, give you perspective if you do get rejected, and help you process things.
You could even plan a fun event when you hit 10 combined rejections - treat yourselves to a nice dinner out!

Getting started is the easiest part.

Create a simple shared Google Doc.
Find an accountability buddy.
And aim to collect five real rejections each.

Not hypothetical ones, or things you almost tried, but actual asks that could reasonably result in a “no.”

Some ideas:

Log each attempt, whether it results in a yes or a no.
Once rejection becomes the goal, everything shifts.
You keep going for bigger and bigger things, and don’t let your self-rejection kick in.
You let others people reject you, and you don’t reject yourself.

Failure, it turns out, isn’t something to avoid, it’s a sign that you stepped outside your comfort zone.
And if you’re willing to track it, share it, and even celebrate it a little, you might be surprised by what you’re capable of asking for.