Part of the deal when you run a business is getting comfortable with the word ‘no’. Clients say no to proposals, investors pass on your pitch, collaborators decline your partnerships, that dream speaking slot goes to someone else, and the article you spent weeks crafting gets returned with a tonne of amendments. It feels like a knockback every single time.
However, if you can learn to embrace rejection rather than avoid it, it might be one of the most valuable skills you can develop as a business owner.
Why rejection cuts so deep
When someone rejects your business proposal, your brain doesn’t process it as “they don’t want this service right now”. Instead, it tends to register as “I’m not good enough”. This isn’t your fault – we’re wired this way.
Entrepreneur Jia Jiang knows this better than most, as a childhood experience of public rejection left him with a fear so deep that it was holding back his entire career. By age 30, despite big ambitions and solid skills, he found himself stuck in a marketing manager role, too scared to put himself out there. His solution was radical: he decided to actively seek out rejection, every day, for 100 days.
The 100 days of rejection challenge
Jia created a list of absurd requests specifically designed to get him rejected: borrowing £100 from a stranger, asking for a burger refill at a restaurant, requesting Olympic symbol doughnuts from Krispy Kreme, and asking to do a staring contest with a CEO.
He filmed every attempt and posted them online to keep himself accountable. The first rejection was brutal when he approached a security guard to ask for £100, got a flat no, and ran away in embarrassment, but he kept going.
Then something unexpected happened: Jia found that by the end of his 100 days, he had actually received 51 yes responses and only 49 no responses. The Krispy Kreme employee not only made his Olympic symbol doughnuts but also gave them to him for free, and the video went viral with over five million views.
More importantly, Jia discovered strategies that dramatically increased his chances of getting a yes, and techniques that made rejection feel less crushing when it did come.
Making rejection your business strategy
While Jia was seeking rejection to overcome fear, author and career transition expert Eleanor Tweddell took a different approach: she built rejection into her business goals from the start.
In 2018, whilst writing her first book, she set herself what seemed like a wild target: get 20 rejections from publishers. She aimed for the 21st pitch to be the one that landed her book deal.
“Every rejection you get is a moment to celebrate because it means you tried,” Eleanor explains. The Do Lectures Publishing was one of her first pitches – they said no – but because she needed to hit 20 rejections anyway, it didn’t feel painful, it felt like progress.
After finding an experienced book coach who became her agent, Eleanor eventually got her yes from Penguin, but by then she’d sailed past her original 20-rejection target. For her second book, she knew it would be even harder, so she prepared herself for 30 big rejections. Over the five years it took to secure that deal, she definitely exceeded that number.
When rejection comes back around
Eleanor’s story gets even more interesting – that original rejection from The Do Lectures in 2018 wasn’t the end. Eleanor had attended a Do Lectures bootcamp in 2016 and felt genuinely drawn to their philosophy. She wanted to be part of their community, not in a “what can I get” way, but out of genuine interest in their thinking.
So she subscribed to their newsletter, followed their speakers, bought their books and attended more of their workshops. She dropped messages to the people involved and kept showing up, even after the rejection.
When her book came out, she pitched directly to their founder to run a course with them about her specialist topics and with no immediate bites, she kept going.
When Do Radio was announced in 2025, Eleanor was giving a talk about change and mentioned her own podcast, Another Door, which had been running for eight years. She casually mentioned she loved audio work and would welcome opportunities to do more.
Soon after, a Do Radio producer messaged her – they were looking for a host for a show about change, and so, eight years after that first rejection, Eleanor became a Do Radio host, proving that sometimes rejection isn’t a door closing – it’s just not your time yet.
What rejection can teach you
Rejection carries data: when your business pitch gets turned down, you’re not just hearing ‘no’, you’re getting information.
Perhaps your timing was off, maybe the market isn’t ready yet, it could be that your messaging needs work, or you’re targeting the wrong audience entirely. Sometimes the person saying no has budget constraints, internal politics, or a hundred other factors that have absolutely nothing to do with you or your business.
The trick is staying engaged long enough to find out. Jia learned that simply asking “why” after a rejection often turned a dead end into useful feedback, and sometimes it even turned the no into a yes.
When you’re rejected, try asking:
- “Can you help me understand what didn’t work?”
- “What would need to change for this to be a yes?”
- “Is the timing wrong, or is it the fit?”
- “Would there ever be a scenario where this could work?”
If you avoid the temptation to run and stay in the conversation, because most people actually want to help if you make it easy for them.
Building rejection resilience
The more you experience rejection, the less it hurts. Your first business rejection probably felt devastating, but your twentieth probably felt annoying, and your hundredth might barely register.
This is why some business owners adopt their own version of the rejection challenge. Set yourself a target: get rejected 10 times this month. Or 20. Or 100 if you’re feeling particularly brave!
Make ridiculous requests you expect to be turned down for:
- Ask for discounts you probably won’t get.
- Pitch to publications slightly out of your league.
- Propose collaborations with businesses you admire.
- Apply for opportunities you think are long shots.
Then track your rejections. Designer Liz Mosley even created a rejection sticker chart specifically for this purpose (available at lizmosley.net/rejection-sticker-chart). Every time you get a no, you stick a smiley face on your chart. It’s oddly satisfying, and it reframes rejection as progress rather than failure.
The abundance mindset
One of the biggest shifts successful business owners make is moving from a scarcity mindset to an abundance mindset when it comes to opportunities. If you’re pitching to one potential client and they say no, that rejection carries enormous weight because you feel like you’ve lost your one shot. But if you’re pitching to 20 potential clients and 16 say no, those four yeses feel brilliant and the rejections barely matter.
This doesn’t mean spray-and-pray; it means not putting all your eggs in one basket and building systems that create multiple opportunities rather than banking everything on a single big break.
Practical strategies for handling rejection
- Set rejection goals
Turn rejection into a game you’re trying to win. Eleanor’s approach of targeting 20 or 30 rejections before expecting a yes completely reframes the experience. Each no becomes a tick on your list rather than a blow to your confidence. If you’re not getting rejected from something every week, are you even trying?! - Keep a rejection list
Eleanor kept track of who rejected her book, then reframed it: “HarperCollins replied to me.” That’s a different relationship than “HarperCollins rejected me.” You’re collecting responses from impressive companies and people, building a list of organisations that know who you are. - Acknowledge the feeling
Don’t bottle it up. Scream into a pillow. Go for a run. Talk it through with your business friends. Let yourself feel disappointed for a defined period, then move forward. Eleanor’s advice: you’re allowed to be sad, annoyed or frustrated when rejection comes your way, but only for a short moment. Then get back up again and keep going. - Get a rejection buddy
Eleanor worked with her agent to manage the rejection process together, which reduced the deflation. Collaborations, community and cheerleaders help minimise the wallow time. Find someone who gets it and process rejections together. - Separate yourself from your business
Your business getting rejected is not you getting rejected. They’re passing on the opportunity, the timing, or the fit, not on your worth as a person. - Review what happened
What can you learn from this? Is there a pattern emerging? Are you targeting the wrong people? Is your messaging unclear? Be honest without being brutal to yourself. - Stay in the conversation
Just because someone says no today doesn’t mean they’ll say no forever. Eleanor kept engaging with The Do Lectures for eight years after her initial rejection. She attended events, subscribed to newsletters, and built genuine relationships. When the right opportunity came up, they thought of her. - Be intentional about who you want to work with
Think about who you want to collaborate with and hang out with, and spend time reading their content. Surround yourself with the right energy. Build genuine interest in their work, not just what they can do for you. - Plan your next move
Channel the frustration into action. What’s your next step? Who else can you approach? How can you improve your pitch? What tweaks would make a difference? - Keep asking
The only guaranteed way to never get a yes is to stop asking. Every successful business owner you admire has been rejected hundreds of times and they kept going. - Reframe rejection as practice
Each no gets you closer to a yes, each rejection teaches you something, each uncomfortable conversation builds your resilience. - Celebrate your courage
You put yourself out there and that’s worth acknowledging. Most people never try because they’re too scared of rejection, so you’re already ahead.
Building a rejection-proof business
While you’re building your personal resilience to rejection, you can also build business systems that protect you from letting rejection derail everything.
- Create multiple revenue streams so one no doesn’t threaten your entire income.
- Build a pipeline of opportunities rather than depending on a single big break.
- Develop relationships with multiple potential clients rather than fixating on landing one dream account.
The goal isn’t to never experience rejection but to make rejection feel like a normal, manageable part of doing business rather than a catastrophic event. As Jia and Eleanor demonstrate, rejection can be a long game and it can be a gift.
