Hit 100 rejections before my first real freelance job. Was it worth it?

I'm trying to figure out if the whole 'grind it out' advice is actually solid or just toxic hustle culture. In my case, I sent out proposals to 100 different people on Upwork over 6 months before one finally said yes to a $400 web design project. That one job led to 3 more referrals, but man, those first 99 rejections felt like a total waste of time. Did hitting a specific number like that actually matter for you, or was it just luck?

3 comments

3 Comments

brooke_murray17d ago

99 rejections and a single "yes" sounds less like a strategy and more like a really expensive lottery ticket that finally paid out. Honestly, I'd say it's a mix of both grinding and luck, but mostly you just got lucky that one person happened to scroll past your proposal at the right time. The grind part is just making sure you're still there when the luck finally shows up.

adam18617d agoMost Upvoted

So you're saying it's basically a numbers game where you just need to be stubborn enough to outlast the no's, @brooke_murray? Does that mean you think persistence matters more than actually improving what you're pitching?

anna71716d ago

Honestly, I've seen a lot of these "99 no's, one yes" posts and they never add up. Nobody is keeping a tally of their rejections like that. You're either trying to sell something bad or you're getting warmed up for real. If you're pitching something solid, you don't need 99 attempts. You need maybe 10 to 15 targeted conversations, not a spam campaign. This whole "grind it out" mindset just makes people feel better about wasting time.