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Rebuilding Your Identity Beyond Success: A Founder’s Guide

Founder Identity

Identity reclamation. That’s what I thought when reading Loom co-founder Vinay Hiremath’s story about reaching financial success and then feeling utterly lost. It resonates deeply with the founders I’ve worked with as an executive coach. While most don’t experience the kind of financial windfall Vinay did, many face the same existential question when they reach “the other side”: What do I do now?

You can read more here: I am Rich, and I Don’t Know What To Do With My Life.

The journey of building a business is all-consuming. Over time, your identity becomes entwined with your company. Your purpose aligns with the firm’s goals, and your personal needs and passions often take a backseat. Then, when the business no longer dictates your every decision, you’re left wondering who you are without it.

Vinay’s story illustrates this vividly. After exiting his business, he found himself searching for direction. He writes candidly about how the euphoria of success gave way to a void. He experimented—trying out new pursuits, but ultimately, he found his next chapter in an unexpected place: studying Physics abroad. It wasn’t about filling the time but about reigniting curiosity and finding something that truly inspired him.

For most founders, the solution isn’t necessarily a return to academia, but the principle is the same. To rebuild your sense of self, you have to look inward—to rediscover the interests, talents, and aspirations that may have been neglected.

My Experience: Building a Life with Layers of Purpose

I don’t have the kind of financial cushion Vinay does, but I’ve been fortunate to find fulfillment through a diverse range of passions. By wearing many hats—executive coach, tech founder, screenwriter, DJ, and music producer—I’ve built a life that energizes me. And because I’m happy and engaged, I’m also a better dad to my kids and a more creative husband to my wife (or so I hope!).

But I’ve been through moments where I felt subsumed by the business grind. We’ve all been conditioned to prioritize performance—whether as employees or entrepreneurs—to the point where our identity becomes one-dimensional.

Rebuilding Your Identity Starts with Small Steps

If you’re feeling lost after stepping back from your business, here are three practical steps to help you rediscover who you are:

(a) Find Out Your Natural Skills (Not Just Your Business Ones)

Strip away the skills you’ve developed for work and ask yourself: What do I enjoy doing, even if there’s no tangible reward? This could be creative pursuits, problem-solving, teaching, or tinkering with new ideas. These skills can reveal passions you’ve ignored.

(b) Meet as Many People as You Can

New ideas and perspectives come from new interactions. Connect with people outside your usual circle. They don’t need to be “useful” in a traditional sense—sometimes the most inspiring conversations come from unexpected places.

(c) Make as Many Mistakes as You Can

Experimentation is key. Allow yourself to try and fail without judgment. Whether it’s learning a new hobby, exploring a different field, or simply traveling somewhere unfamiliar, mistakes are opportunities for discovery.

Rekindle Your Spark

Rediscovering your identity is not about rushing to find the next big purpose. It’s about creating the space to explore what truly excites you. As Vinay’s journey shows, the path forward might not be linear, but the destination is worth it: a life that feels authentically yours.

If you’re in a similar situation and want support in finding your way forward, write to me. Let’s work together to help you rediscover your spark.

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Hutton Henry
Hutton has worked with Private Equity Portfolio firms and Private Equity funds since 2015. Having previously worked in post-merger integration for large firms such as Ford and HP, Hutton understands the value of finding issues prior to M&A deals. He is currently the founder of Beyond M&A and provides technology due diligence for VC, PE and corporate investors, so they understand their technology risks before entering into a deal.

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