Overcoming Setbacks: 18 Entrepreneurs Share Coping Strategies

Looking back on my entrepreneurial journey, which began in 2004, becoming severely ill was the single greatest threat I faced. When you are the business, your absence can feel like an existential threat to your livelihood. In fact, it truly was an existential threat a few years ago.

After a sports accident, I had to undergo several surgeries over a period of 14 months before I was able to use the upper left side of my body properly again. During this time, I also developed Hashimoto’s thyroiditis, which initially took a very debilitating course. This condition left me with unpredictable energy, pain, and mobility issues. I could no longer sit at a desk for eight hours, nor could I guarantee that I would keep scheduled appointments.

But I didn’t quit, as that would have been the end of my business. I re-engineered my environment and embraced the identity of a “chronicpreneur.”

I moved my operations to my bed or recliner on bad days. I abandoned rigid digital to-do lists that caused anxiety and replaced them with a “String Wall” — a physical string across my room where I clipped index cards with major tasks. I could only take one card down at a time.

This approach greatly helped me confront my feelings of limitation and overwhelm by giving me the necessary structure and a sense of self-efficacy. Chaos became small, manageable steps. Consistent prioritization of tasks also meant that trivialities could be ignored.

By the same token, I implemented a “Light Day” protocol. Instead of cancelling everything when a flare-up hit, I categorized days as “Heavy” (calls, deep work, complex decisions) or “Light” (admin, learning, low-energy tasks).

The outcome, after almost two years of recovery, was this: I sustained my business by molding it to my body’s needs rather than forcing my body to fit the business.

Many solopreneurs have not only survived prolonged illness but also used it to forge more resilient, profitable businesses. I followed their lead and found inspiration for my own struggles.

Adaptation was key for me. I consider it a life-changing lesson that still shapes my solopreneurship and colors the way I face and confront adversity to this day.

One of the biggest setbacks in my entrepreneurial journey wasn’t a single moment — it was the season when everything that had “worked” stopped working at once. A business that had been comfortably at multiple six figures slowed down, a launch I’d poured myself into underperformed, I was exhausted from years of overachieving, and life outside of work was demanding more of me than ever. It felt as though my identity as “the one who always figures it out” had cracked. Instead of forcing another big push, I did something that went against every instinct I had: I deliberately shrank my goals, simplified my offers, and let myself rebuild at a smaller, saner scale. It was humbling, but it was also where my next level of clarity came from.

The coping strategy I’d recommend is what I call micro-stability: when everything feels like it’s falling apart, stop trying to fix your entire life and business with one sweeping strategy. Stabilize tiny, specific anchors first — one daily non-negotiable for your well-being, one simple revenue stream you can lean on, one clear person you can be honest with about how hard it is. Those small points of stability give your nervous system room to breathe, and from there you make much better decisions. Big comebacks are almost never a single heroic move; they’re a series of calm, grounded micro-moves made when you finally stop pretending you’re not underwater.

The biggest setback for me in Tumble’s early days was having to scrap an entire additional inventory run for our first batch of rugs after months of iteration because the materials didn’t pass our spill-proof and washability tests. As a bootstrapped startup, I felt utterly pressured and full of self-doubt that maybe my co-founder, Justin, and I had committed to chasing an idea that wouldn’t work at scale at all. I spent weeks locked in paralysis, which I could probably have termed existential dread.

What got me past that paralysis were narrow, specific targets that, at worst, felt meaningless compared to the giant obstacle I had to overcome but were actually crucial to start moving with momentum again. For us, this meant breaking down the relaunch of the scrapped inventory, which had failed tech specs, into separate goals like redoing a single material swatch and passing it through only one round of stress tests in the laundry. These small wins helped restore our confidence, provided some social proof that we were still moving despite everything, and helped us finally make decisions that got us out of paralysis once and for all. After just a handful of these micro-wins, our momentum started snowballing, and by the four-month mark post-paralysis, we had new prototypes effectively passing tests.

I’ve seen the same approach work for some of my friends who are entrepreneurs, too. The key to overcoming setbacks is breaking down your recovery steps into the most granular levels you can think of. Set the bar for each action so low — at nearly infallible levels — that you can actually chip away at your goals, rebuild your momentum, and shift your mindset away from panic and paralysis and back into movement. The brave front will follow your momentum.

I never expected downsizing to become such a defining part of my career. When you build something from the ground up, closing a location feels like a failure on paper — even when you know it’s the right move. I poured years into running multiple gyms, growing teams, and trying to keep pace with what I thought growth was supposed to look like. When it became clear that the model wasn’t sustainable for the life I actually wanted, I had to make the call to shrink rather than expand. That decision hit harder than I ever let on.

The real setback wasn’t financial; it was about identity. I had wrapped so much of who I was into being the guy with multiple gyms, the operator with big ambitions, the person who could handle everything. Walking away from that forced me to sit in the discomfort of rebuilding — not the business, but my sense of direction.

What helped me cope was being honest about what was happening without catastrophizing it. I let myself acknowledge the loss, the frustration, and the embarrassment, but I didn’t let those emotions dictate the story. I treated the downsizing like any other problem: I assessed it, understood it, and found the next position I could act from. That mindset kept me from spiraling and allowed me to rebuild a business that actually supports my life rather than consumes it.

If you’re dealing with a setback that feels tied to your identity, the best strategy is to separate the role from the person. Your business is something you do, not who you are. Once you see that clearly, you give yourself permission to make necessary moves — even the hard ones — without feeling like you’re losing yourself in the process.

A go-with-the-flow culture won’t get you through chaos. Lock it down instead.

Our worst setback actually wasn’t a single event. It was more of a change in mindset. We’d worked hard and doubled down on early wins, and Kronus was humming along. We had media placements, inspired clients, and a totally relentless team.

When I looked back, however, I saw that we’d gotten lazy. We adopted a “just get it done; we can figure it out as we go” mentality. As we grew, this casing of dirt on a structure’s beams almost did us in. It started small: one missed deadline, an overlooked detail, or a rule we thought we could bend. In the fog of the unknown, roles got blurry, and no one felt fully motivated to check details or enforce the rules.

And then the firestorm hit. It wasn’t earth-shattering, but a bad client launch caused the team to take it personally, and we were broken for a bit. We’d reached our limit of chaos tolerance.

We threw out the go-with-the-flow mantra. We built a roles-and-responsibilities chart for every key job, with escalation paths and a no-excuses approach. And the beauty is that once go-with-the-flow is out, everyone can run at full speed again.

Teams flourish under pressure, especially when they communicate. Clear expectations and full ownership are the fastest way to give people their lane. We continue to operate with this overlap of no-excuses standards, leadership in every role, and magical teamwork every day. When the stakes are high, it’s the bedrock on which we build.

This works for any endeavor in which people are deluded into hustling against chaos. It’s better to build clarity and understanding first.

The one mental trick that actually works:

Founder adversity is around every corner, and if you’re driven, your worst nemesis is you.

When I started, I would overanalyze every error and double down on effort to fix it. The never-enough mindset cleared any space I might have used to build confidence and left me burned out and despairing.

The hardest thing to learn was this: when things go sideways, be as relentless in self-kindness as you are in ambition and drive.

After our setback, I built in a ritual. On the worst days, I would take five minutes to write down everything we got right or a single thing I admired about the team. That breeze of kindness was a tiny sailboat that kept the despair from sinking me.

The setback that shaped our growth the most was losing our biggest client. One Monday morning, they emailed to say they no longer needed our services. It was a $180k-per-year account — 40% of our revenue — and the floor fell out. Panic hit instantly. However, that loss ultimately became the strongest growth catalyst we’ve ever had.

In the days after, I realized the real mistake wasn’t losing the client — it was allowing any single account to hold that much weight. That realization pushed us to adopt a rule: no client should represent more than a small percentage of revenue. Over the next 18 months, the agency expanded its model. We went from three revenue streams to twelve. Instead of chasing only big accounts, we productized smaller services. Instead of working in one vertical, we used early clients as case studies to launch offers across fifteen industries.

The result? Eighteen months later, CSP’s revenue was 250% of what it had been; no client represented more than 11%; and the agency became faster, more innovative, and far more resilient — which paid off again when 2020 hit.

What saved us that first week was a set of brutally honest, collaborative conversations with key team members. We didn’t get emotional or reactive. We created structured time for analysis, thinking, and open debate. On the Monday after the loss, we held several “decision sprints”: quiet time to review what had happened, followed by an all-hands meeting to gather ideas. The rest of the week alternated between focused work and short alignment meetings. That cadence repeated until a clear path forward emerged.

My advice to founders is to create a small circle you can be vulnerable with — people who will challenge your assumptions and expose blind spots. Cycle through honest conversations, reflection, and iteration. Every major comeback at CSP traces back to four or five rounds of this process. The more intentional you are about identifying what you’re missing — or avoiding — the faster you move from panic to progress.

One of the most challenging setbacks on my entrepreneurial path occurred when our early product wasn’t embraced by restaurant owners. We thought we understood the hiring challenges that restaurant owners faced, but the feedback we received made it clear that we had totally missed the mark. This was incredibly disheartening, as we had already dedicated months of effort and a tremendous amount of hope.

What ultimately pushed me through was treating the setback as data rather than a personal disappointment. I went back to basics, spending weeks talking directly with small restaurant owners about what was working and — most importantly — what was not, so we could make our platform better. I asked some uncomfortable questions about the platform and began to recode everything. We built a new process, changed our matching system, and focused heavily on filling roles that restaurants were struggling to fill quickly. The end result was a product that finally resonated with the people we were trying to help.

My most significant coping strategy is what I refer to as a “pause ritual.” When it feels like everything is about to fall apart — or everything is already falling apart — I stop and step away to reset before making a rash decision. For me, that looks like a long walk and a journal entry detailing the struggles I’m going through, being frank and honest about what I’m struggling with. I force myself to create three concrete next steps so that, even if those action steps don’t immediately resolve the situation, the exercise quiets the emotional noise and puts the situation back under my control.

When I launched my coaching business, I assumed the biggest demand was “career-transition coaching for recent graduates.” I built a slick site, filmed a 30-day video program, and ran ads targeting 22- to 25-year-olds. The response was tiny — most prospects wanted free advice, and the market was already flooded with university programs and low-cost bootcamps. Within a few months, I realized I’d picked a saturated, price-sensitive niche and was burning cash without traction.

I paused, reframed the situation as a simple fact (“my graduate-coaching model didn’t achieve product-market fit”), and asked what unique advantage I truly had. My ten years of leading high-performing teams gave me deep insight into executive-level leadership, so I pivoted to strategic-influence coaching for mid-career managers — a segment willing to invest in that expertise. I reached out to a handful of senior professionals, offering a free “Influence Audit,” refined my messaging, and soon secured retainer clients. The micro-reset loop — pause and reframe, take one tiny actionable step, then review — turned a costly misstep into a thriving, better-aligned coaching practice.

When I started my company, I faced initial doubts from others about my unique approach to using creative methodologies in corporate learning and development. The most effective strategy I used was reframing my thinking from, “What if this doesn’t work?” to, “How might I make this work?” This shift in mindset allowed me to think in terms of possibilities and problem-solve to find viable solutions. For example, I began reaching out only to industries and companies that I knew already valued creativity. This transformed fear into productive problem-solving and allowed me to embrace challenges as learning opportunities. I recommend that entrepreneurs facing adversity focus on this question-reframing technique, as it channels energy toward solutions rather than dwelling on obstacles.

I did not just hit a setback; I was dropped into a crater.

In December 2019, while driving home from a ten-day meditation retreat, I learned that my spouse of thirty-one years had burned alive in a car accident hours earlier. With one call, everything collapsed at once. My income was cut in half, my health insurance was gone, and a life built in partnership was suddenly reduced to a single voice in an empty house. Then COVID hit and shut the world down. There was no pause to grieve and no time to stabilize. I still had clients, bills, and a business that needed decisions.

My spouse had also been an entrepreneur, and keeping his business going felt like the right thing to do because people depended on it. I stepped in, did the work, and tried to keep it afloat. The surviving co-owner had other plans: he hired a lawyer and tried to force me out. It got messy quickly. In the end, he succeeded. The business slipped away in a tangle of paperwork and conflict.

The strange truth is this: losing that battle turned out to be a relief. It pushed me back into my own lane — the one I never should have stepped out of. Once the dust settled, I rebuilt. I expanded my coaching practice. I pursued my life and health license, because offering supplemental benefits meshed seamlessly with my work with business clients. I deepened my work as a substance abuse counselor and DOT SAP provider. I even tried a traditional job as a clinical director and quickly discovered that I am not meant for someone else’s time clock. I have been self-employed since 2006; that rhythm is in my bones.

The coping strategy that carried me through it all was equanimity — not forced calmness and not pretending things are fine. The real thing was built through years of vipassana and anapana practice — more than two hundred sixty days in silent meditation.

Equanimity allows you to see clearly amidst chaos. Imagine two pilots whose engines are failing. One panics, spirals, and loses the ability to act. The other stays grounded in reality as it is and works on the problem. Same crisis, different mindset, different result.

That steadiness is what allowed me to pivot, diversify, and adapt instead of breaking.

Adversity will take things from you — sometimes more than you ever imagined. However, with equanimity, you can keep moving, keep choosing, and keep shaping the life that comes next.

One of the biggest setbacks in my entrepreneurial journey happened when a developer I trusted didn’t deliver what was promised, especially at a very important stage of the project. It caused delays, stress, and extra work, and for a moment, it felt like everything was falling apart. What helped me overcome it was staying calm, focusing on solutions, and reminding myself that challenges are part of building something real. I learned how important it is to choose the right partners and to protect my work with proper checks and handovers.

My advice to anyone facing adversity is this: slow down, take a breath, and deal with it one step at a time. When you stay steady, you think more clearly. And try to keep supportive people around you — sometimes just one good conversation can give you the strength to move forward again.

When my company introduced a new service line that failed to generate anywhere near the number of customers anticipated, that shortfall became an obstacle to the company’s progress. While it was not a total disaster, it was sufficient to impede the company’s momentum. I took a step back and viewed it as a sign — an indicator that we needed to make some changes — rather than as a complete failure. Therefore, we changed the service offering by removing two features that were adding to the product’s complexity for founders. The change also provided the team with a way to describe the value proposition much more clearly. After a couple of weeks, the conversations felt less complicated, and the conversion rates continued to increase at a steady pace.