The Rejection You're Most Afraid Of Is the One You're Giving Yourself.
The psychology behind why founders reject themselves before anyone else gets the chance.
A newsletter for founders and leaders uncovering the patterns behind how they lead, decide, and scale. A new issue every week.
Inspired by my recent conversation with Chandrika Maheshwari, co-founder and CEO of Quivly, where she's building an AI workforce for post-sales teams.
How many doors have you quietly closed before anyone else had a chance to answer?
Sit with this question for a moment.
The Belief Worth Challenging
There’s a belief that runs deep in high-performing founders and executives: you need to be ready before you act. Ready before you start the company. Ready before you make the ask. Ready before you put yourself in the room where someone might say no.
It sounds responsible. It looks like preparation. And in many professional environments, it gets rewarded. The person who shows up with the polished deck, the airtight plan, the fully baked product gets praised for their discipline.
But there’s a version of “getting ready” that has nothing to do with preparation. It’s a version where you keep adding items to the checklist because finishing the checklist means you’d actually have to do the thing. Where you tell yourself you need one more credential, one more hire, one more quarter of data before you can make the leap.
The belief is that readiness is a prerequisite for action. But for founders operating at the edge of what they’ve done before, readiness is often just a sophisticated form of self-rejection. You say no to yourself so that nobody else has to.
Chandrika’s journey from consulting to Google to founding two companies reveals something different: the moments that changed her trajectory weren’t the ones where she felt ready. They were the ones where she acted before the checklist was complete.
What It Actually Looks Like
When Google reached out to Chandrika about a product marketing role, she had studied engineering and worked in consulting. She had no marketing background. Her first instinct was disqualification.
“I felt like I had no business even interviewing for that position. I didn’t know the first thing about marketing because I had studied engineering. I’d worked in consulting. I was like, I think they have the wrong person.”
But then she made a small, decisive shift. She hadn’t applied. They had reached out. So instead of deciding for them, she let the process play out. She got the job. She became the first product marketing manager on the ad side of things at Google India, part of a team of twelve doing marketing for all Google products in a country of over a billion people.
It was inside that role that she began to see how deeply the pattern of self-rejection ran. She described needing to unlearn the idea that someone had to give her permission to act. In her words, being “high agency” meant recognizing that no one was going to hand her a green light. She had to move without one.
“No one needs to give me permission to do things. I just need to be able to make those decisions. Being high agency is one of those things I look for in the hires that we bring on at Quivly.”
Later, Chandrika introduced a framework she’d encountered that crystallized this pattern: ask culture versus guess culture. In guess culture, you do the mental work of predicting someone’s answer before you ever ask the question. You only reach out if you’re fairly sure the answer will be yes. In ask culture, you ask the question and leave it to the other person to respond however they see fit.
The distinction matters because guess culture feels like emotional intelligence. It feels considerate. But it also means you’re making decisions for other people based on your own projections. You’re filtering out opportunities before they have a chance to exist.
This pattern showed up again when Chandrika knew she wanted to start a company. She had the desire before business school, but she kept adding prerequisites. Get the visa sorted. Learn product management. Build a track record. Each step was legitimate on its own. Together, they formed a wall between intention and action.
The shift happened at Plaid. She was preparing for a meeting, writing a document, and something clicked.
“I’ve been collecting logos on my resume. I’ve been building all these safety nets. When do I feel like I will be ready? There’s never going to be one day I will wake up and be like, today I’m prepared. Here’s the checklist and I’ve done each one of the things and now I’m ready. So I just have to take the plunge.”
She left to start her first company. It didn’t work out the way she planned. She scaled it for twenty months, hit headwinds in the regulatory and macro environment, and made the decision to wind it down and return capital to investors. Then she started again. She found her co-founder Tanay Agrawal through what she describes as a serendipitous reconnection, went through a rigorous co-founder dating process, and launched Quivly.
When asked what she looks for in hires now, her answer maps back to the same insight: high agency and curiosity. The willingness to act without waiting for a signal that may never arrive.
If this resonates, forward it to a founder who keeps adding one more thing to the list before making the ask.
From the Coaching Room
I was recently working with a founder who was searching for early pilot partners. Without putting in much effort, just attending a few events, she already had a handful of leads. Real people who had expressed genuine interest in what she was building.
I asked her a simple question: what’s stopping you from asking these leads to be part of your pilot? She paused. Her answer was that her product didn’t feel ready yet. She wanted to polish it more before putting it in front of anyone.
But that’s exactly the point of a pilot. You build with real partners who will inform the product. The product doesn’t get ready in isolation. It gets ready through the conversations she was avoiding. In our session, she decided she would reach out to her existing leads and do additional cold outreach to find a few more pilot partners for the next iteration.
She wasn’t self-rejecting because her product wasn’t ready. She was self-rejecting because the conversations are hard, and we feel vulnerable when someone might say no. So we keep perfecting the thing instead of doing the part that’s toughest to do.
What the Research Actually Shows
We Dramatically Overestimate How Often People Will Say No
Vanessa Bohns, a social psychologist at Cornell, has spent over a decade studying what happens when people make requests of others. Across more than 14,000 participants, her research on what she calls the "underestimation-of-compliance effect" found that, on average, people underestimate how likely others are to say yes by approximately 48%.¹
The mechanism behind this is straightforward: when we imagine making a request, we focus on all the reasons someone might refuse. But we fail to account for the social pressure the other person feels to comply. Saying no to a face-to-face request is awkward, and people avoid awkwardness.
For founders, this means the cold email you didn’t send, the partnership you didn’t propose, the investor you didn’t approach likely had a much higher chance of landing than you assumed. The cost of not asking isn’t neutral. It’s compounding.
Action Doubts Are the Real Bottleneck Between Intention and Entrepreneurship
Michael Frese and Michael Gielnik's comprehensive review of the psychology of entrepreneurship, published in the Annual Review of Organizational Psychology and Organizational Behavior, examined a decade of research on what separates people who intend to start companies from those who actually do.²
Their findings center on action regulation theory: the critical gap isn’t between having an idea and wanting to act on it. It’s between wanting to act and actually acting. The primary inhibitor is what they call “action doubts,” a state of uncertainty about whether you’re ready or capable of implementing your intention. In contrast, self-control and what Frese terms “personal initiative,” defined as self-starting, proactive behavior that overcomes barriers, strengthened the connection between intention and action.
The research suggests that the founders who succeed aren’t the ones who eliminated doubt before starting. They’re the ones who started while the doubt was still there.
How to Stop Rejecting Yourself Before Anyone Else Can
Chandrika’s story and the research point to the same conclusion: the biggest barrier to action isn’t external rejection. It’s the internal kind. Here are four ways to interrupt that pattern.
Name the projection before it becomes a decision. The next time you catch yourself deciding not to ask for something, pause and ask: am I responding to real information, or am I guessing what the other person will say? Chandrika’s suggested framework of ask culture versus guess culture distinction is useful here. If your reason for not reaching out is based on what you think someone will think or feel, that’s projection, not data. Write down what you’re assuming and notice how often the assumption is doing the work of a decision you never actually made.
Separate legitimate logistics from emotional safety nets. Chandrika needed to sort out her visa status before starting a company. That was a real constraint. But she also told herself she needed to work in product management first, build a longer track record, and accumulate more experience. Some prerequisites are structural. Others are ways of staying comfortable while feeling productive. Audit your own list of “things I need to do first” and honestly label each one: is this a real dependency, or is it a way to delay the vulnerable part?
Set a “decision by” date for open questions. One of the reasons readiness traps persist is that they never force a decision. There’s always one more thing to learn, one more conversation to have, one more quarter to wait. Put a date on it. Not a deadline to be ready, but a deadline to decide whether you’re going to act or not. The date removes the illusion that you can indefinitely prepare without choosing. When the date arrives, you either go or you consciously decide not to. Both are better than drifting.
Make the first ask small and specific. Self-rejection often comes from imagining the biggest possible version of the ask. You don’t picture sending one email to one potential partner. You picture the entire fundraise, the full go-to-market, the public launch. Scale the ask down to its smallest honest version. One conversation. One pilot request. One intro. Bohns’ research shows you’re already underestimating how likely people are to say yes. Start with a version of the ask that feels almost too easy, and let the momentum build from there.
The Bigger Picture
There is a particular kind of courage that doesn’t look dramatic from the outside. It’s not the grand leap or the bold public declaration. It’s the moment where you send the message instead of editing it one more time. Where you ask for the meeting instead of waiting until you feel more qualified. Where you start the company instead of adding one more line to the resume.
Chandrika built and shut down a company, then started another one. She took a role she felt unqualified for and grew into it. She left a comfortable position at a company where the golden handcuffs were already forming. None of those moments came with a guarantee.
“There are never any guarantees in life. And if this is what I really want, I should not let fear keep me from pursuing my dreams.”
That’s the real inner game here. It’s not about becoming fearless. It’s about noticing the moment you start doing someone else’s job for them, deciding in advance what they’ll say, and choosing to let them answer instead.
The checklist for readiness will never be complete. At some point, you have to check yourself and ask: are these valid reasons for not starting, or am I just holding myself back? The founders who build things that matter are not the ones who waited until every condition was perfect. They’re the ones who decided the ask was worth more than the comfort of never having to hear no.
Founder Circle
If something in this newsletter hit close to home, you don’t have to sit with it alone. Founder Circle is a 90-minute live session where ten founders each bring one real challenge and leave with the clarity to act on it.
P.S. What’s one ask you’ve been putting off because you’re not sure how it will land? I read every response.
I’m Dar Patel, an ICF-certified executive coach (PCC) and founder of Little Pursuits. I partner with founders and executives through the leadership inflection points: the identity shifts, the hard conversations, the decisions you keep carrying alone. This newsletter is where that work meets the page. Find me on LinkedIn.
If you want to go deeper to check out the references used in our research:
¹ Bohns, V.K. (2016). “(Mis)Understanding Our Influence Over Others: A Review of the Underestimation-of-Compliance Effect.” Current Directions in Psychological Science, 25(2), 119-123. A review of multiple studies finding that people systematically underestimate others’ willingness to comply with direct requests, with the average underestimation at approximately 48%.
² Frese, M. & Gielnik, M.M. (2023). “The Psychology of Entrepreneurship: Action and Process.” Annual Review of Organizational Psychology and Organizational Behavior, 10, 137-164. A comprehensive review finding that “action doubts” inhibit the translation of entrepreneurial intentions into action, while personal initiative strengthens it.
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