Helping a Dev Rediscover His Entrepreneurial Drive
How I coached a burned-out developer to overcome perfectionism, find clarity, and pursue his passion.
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Are you an experienced software engineer frustrated with the hiring practices in our industry? Companies seem to ghost you in the middle of the interview process without any effort to provide feedback. Even if you do land a job, you might find yourself laid off within a few months. It’s a frustrating cycle that so many developers face.
Today, I want to share a real coaching session I did with a client named Matt, who has been through similar situations over the last couple of years. I’ve worked with him off and on during that time, and he’s done some amazing work to bring himself from a pretty dark place to a much better one.
As you read this, I hope you’ll look for your own career story within the themes Matt’s facing. I think you’ll find that a lot of Matt’s struggles and breakthroughs are relatable. His courage to share his journey here is something I really appreciate, and I hope it inspires you to keep going through whatever you’re dealing with.
Rediscovering Progress in a Low Period
When Matt and I reconnected, it had been a couple of months since our last session. As he brought me up to speed, he told me about his latest round of job applications. Predictably, he had been ghosted by companies despite pouring effort into interview preparation.
Rather than getting bogged down in frustration, Matt used this downtime to focus on personal development. He started working with a new counselor, dug into some deeper issues he’d been avoiding, and channeled his thoughts into extensive journaling. The result? Clarity.
Burnout had been holding him back more than he realized. His old habits—eating out too much, avoiding exercise—were actually symptoms of burnout rather than causes. Once he recognized this, he made changes. He began exercising more consistently, eating healthier, and embracing a slower pace to allow for mental recovery.
He also recognized that recovering from burnout can take years, not weeks or months. That realization helped him be kinder to himself during the process.
The Trap of Perfectionism
One of Matt’s most significant breakthroughs was recognizing how perfectionism was sabotaging his progress. He had long seen perfectionism as a sign of high standards or even ego. But what he came to realize is that it was rooted in self-doubt.
Perfectionism can become a form of avoidance. When you’re afraid of failing or not living up to an impossible standard, it’s easy to retreat into planning, learning, or “waiting for the right moment.” For Matt, that looked like obsessively journaling and trying to construct a perfect career plan. He wrote 26 journals, each around 10 pages, within two months.
“Taking imperfect action is always better than waiting for the perfect moment. Sometimes, you just have to get moving and adjust as you go.”
He found himself at a crossroads where he realized the journaling had become another avoidance tactic. Instead of moving toward action, he was stuck in analysis. He decided that it was time to shift gears and focus on tangible progress.
Shifting Focus from Career to Self
Much of Matt’s initial coaching focused on figuring out his career path as an employee. He wanted to transition from backend development to full-stack development and broaden his skill set.
But over time, it became apparent that Matt’s real interest was entrepreneurship. This wasn’t a new discovery. It was something he had been passionate about since childhood but had buried under the more conventional approach of pursuing “stable” employment.
The more we talked, the more it became clear that Matt thrived on building things from scratch. What excited him about software development was the potential to create a product or service that could make a real impact. The entrepreneurial side of the work was what got him motivated.
The False Sense of Security in Employment
Matt was wrestling with a tough question: Should he continue trying to find a job or should he go all-in on entrepreneurship? He had been laid off from a previous role after just five months, despite being excited about the culture and leadership.
That experience highlighted a truth many developers ignore: the illusion of stability in traditional employment. It’s tempting to see a job as a safer option than striking out on your own. But Matt’s recent history demonstrated how fragile that stability can be.
I challenged him to consider whether he was clinging to the idea of safety by pursuing jobs that may not actually be safer than pursuing his entrepreneurial interests.
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Exploring Business Ideas
Matt’s interest in entrepreneurship aligned with his personal experiences. He had recently been running a small interview study group where they would practice mock interviews, work through problems together, and provide each other with feedback.
This led him to an idea: a flashcard-based tool to help developers with interview preparation. By offering something simple yet effective, he could create a valuable resource for developers who are struggling to navigate the interview process.
Even more importantly, Matt was excited about the idea. His own frustration with job hunting and helping others through the same struggles gave him a genuine sense of purpose and passion for the project.
The Bigger Challenge
But having a good idea isn’t enough. Matt needed to think beyond the tool itself. What could he offer that would be 10x better than what already exists? Could he make the experience so compelling and helpful that it stood out from other interview prep solutions?
I encouraged him to consider how his solution could differentiate itself not only in functionality but also in user experience, aesthetics, and customer care. Was there a way to offer something truly unique and valuable to both developers and employers?
Moving Forward
The next step for Matt is to do more research, brainstorm improvements, and validate his ideas. Even if this particular project doesn’t work out, the process of developing it will provide him with valuable skills and insights he can apply to future endeavors.
As someone who’s been through my own ups and downs with career transitions and entrepreneurship, I can tell you that taking imperfect action is always better than waiting for the perfect moment. Sometimes, you just have to get moving and adjust as you go.
I hope Matt’s story gives you the same encouragement it gave me. No matter how tough things get, there’s always a path forward if you’re willing to look for it.
About the THRIVING TECHNOLOGIST show
On YouTube and all major podcast networks, Jayme shares teamwork and leadership strategies, guidelines for healthy company culture, and stories about real projects so you can have a sustainable career in the software industry.
Jayme Edwards
A family man and veteran of nearly 40 software projects, Jayme experienced many wins and losses over his career as an architect and consultant.
Now he's coaching software developers, managers, and business owners to overcome challenges in the IT industry - so they keep growing.