How to make rejection suck less

“We regret to inform you…” is not my favourite thing to read when I open an email. Unfortunately, rejection is a part of life, and it’s definitely a part of life if your life involves pitching or applying to things. It’s never a particularly enjoyable feeling, but the good news is that there’s a lot you can do to take the sting out of things. One of my favourite reminders is that rejection is just redirection, and that’s proven to be true for me multiple times, no matter how frustrated I was at not getting the opportunity. Things really do have a way of working out one way or another.

Almost a decade ago, I applied to a job in Amsterdam that looked perfect for me. I got through about six interviews and tasks (in the days before remote interviews were acceptable, no less), and was in the final two. I spent a week praying to higher powers that I’d get the job. When I got the rejection email, I was pretty frustrated, but later that day, the hiring manager called me on her personal phone. She wanted to give me a heads up that she was leaving, it was an awful place to work, and that she was relocating to Chicago to work at her dream company. A rollercoaster of emotions that day, for sure, but it all worked out.

Other things in my museum of failures include:

• 90% of my article pitches getting rejected (pretty standard really)

• Almost getting kicked out of my Bachelor’s because I failed a core course twice (Predicate Logic, something that has had zero relevance to my life in any capacity)

• Lots of cold messages that never got responses

• We didn’t get what I thought was my dream apartment in Paris, because the landlord decided to let her relative live there after all

• Getting rejected from my Master’s degree in 2018 because I didn’t meet the admissions requirements… I had to challenge the rejection four times with increasingly creative approaches before they relented and admitted me

None of these things have particularly negatively impacted my life, but they didn’t feel fun at the time. If fear of rejection is stopping you from going for the things you really want, here’s what you can do.

First things first, a mindset shift. Let’s look at some of the classic statistics around failure. It’s a well known fact that 90% of startups fail, but did you know that over 75% of venture-backed startups fail? This means that three quarters of startups who have successfully raised VC funding—where a number of analysts or investors or whoever have done a lot of number-crunching and decided to invest—still don’t make it. Even so, over 5 million businesses are founded every year in the United States alone. These people are chasing success, and accept that failure is an inevitable part of the journey. As Walt Disney once said, “The people who succeed are the ones who keep going after everyone else has stopped.” You’re going to get rejected one way or another, whether it’s for jobs, romantic relationships, grants, funding, friendships… you’ve just got to find ways of handling rejection.

There’s this really great challenge going viral at the moment, where people try and get rejected 1000 times during 2026. It’s become so far-reaching that it’s even been covered in Vogue. Since you obviously can’t guarantee rejection, the idea is to apply for as many cool opportunities as possible, and to shoot your shot where you usually wouldn’t. In racking up rejections, you’ll desensitise yourself to the feeling, but of course in practice you’ll end up scoring a few (or more!) big wins. I love the idea of this because—if it’s the idea of rejection that’s stopping you from putting yourself out there—the challenge totally reframes the process so that rejection is something you’re actually seeking. In doing so, you’ll get used to all the ‘no’s until it’s just water off a duck’s back (an expression I hate, incidentally).

One of my favourite hacks when I’m pitching for freelance work is to set myself up for success either way. This is not official advice, so don’t quote me on this, but I usually price projects depending on how much I want them. If there’s a big name brand involved that I’m dying to have on my CV, I can flex my daily rate a little. If there’s a project with an NGO whose mission I’m passionate about, I can slash my rates as needed, as long as I have the time. And if a project comes across my virtual desk that I’m not very keen on, I’ll often send a proposal at double my normal rate. This sets me up for a nice win/win situation: either I’m too expensive for them, and I don’t have to do the project, or they say yes (which has happened a surprising number of times), and I get double the money for a project I’m not that excited about. Over time, this averages out to mean I’m working on a really interesting range of projects that keep me inspired, motivated, and well-paid.

This is one of my not-so-secret rules to live by. Whenever you want something, make sure you’ve always got more irons in the fire than you think you need. This goes for most things. If you’re applying for jobs and you’re in the final round for two or three, keep applying—it’s not over until you’re physically walking into the office for your first day. The same applies for finding freelance work: it always takes a little more work than expected to land your next great project.

This is why I love the 100 Connections Challenge, my handy little approach to changing your life. The reality is that you likely won’t need to speak to 100 people in order to achieve your goal, but it never hurts to play it safe. By pushing yourself to speak to 100 people (rather than 20 or 30, for example), you open yourself to exponentially more opportunities, including those that will germinate later down the line. This is something I used to do when applying for full time jobs in the past; every time I’d get a rejection email, I’d immediately apply to three more roles. There’s something about the momentum that keeps your spirits up. Or, as Newton’s Law of Inertia says, things at rest stay at rest, and things in motion stay in motion. As much as a rejection call or email might sting, you always feel better knowing you’ve got lots of other irons in the fire.

This is perhaps the most important one of all. We’re all human, and no matter how thick your skin, rejection can get you down if you get multiple blows in a row, or if the opportunity was something you really wanted. The antidote is to come up with rejection rituals: little pick-me-ups that make you feel better every time you get that “sorry but no”. This could be anything from a commiseration cocktail to a ranting call to a friend (my preference), or the more zen approach of taking a yoga class. I’ve heard of people allowing themselves a 30 minute pity party where they can feel sorry for themselves, but once the clock is up they’ve got to get on with their day. For the pyromaniacs among us, I’ve also heard writing something on a piece of paper and then burning it (outside, safely, blah blah blah) can help. Google suggests dancing to energetic music like “Good as Hell” by Lizzo, but I think she might still be cancelled (it’s hard to keep track these days), so proceed with caution.

So there you have it — no one enjoys getting rejected, but it’s the price you’ve got to pay if you want a big and exciting life. Keep putting yourself out there, try not to let the bad news get to you, and aim for multiple shots on goal—you’re bound to hit the jackpot.

On the Connection Pending Substack, we unpack the art (and science) of connection: from who to meet and how to meet them, to building your own ecosystem and creating those right-place-right-time moments that spark opportunity, whatever your goals in work of life. Start here with The 100 Connections Challenge — it might just change your life... You can find Phoebe at the imaginatively named phoebedodds.com.