Challenges Faced by Entrepreneurs and How to Overcome Them

Estimated read time 13 min read

We’ve all seen the cliché entrepreneurship cover story: A founder starts a business, it becomes an overnight success, they scale fast, and so does their bank account. Their rags-to-riches story makes it all look so easy, doesn’t it?

The reality is, not every entrepreneurship venture is that smooth-sailing growth story. For every business owner experiencing sunshine and rainbows, there are many others living under gray, stormy skies.

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Entrepreneurship, after all, is not an easy path. It’s the less-traveled one, with more treacherous terrain. It comes with higher rates of failure, financial instability, unknowns, and stiff competition. And despite what so many say, it’s incredibly difficult to create a successful business.

It’s no surprise then that 72% of entrepreneurs are directly or indirectly affected by mental health issues, compared to 48% of non-entrepreneurs. With the number of entrepreneurs estimated at 582 million worldwide, this issue impacts a hefty 8% of the global population. While self-doubt can be a challenge for virtually everyone, it can be especially hard to deal with as an entrepreneur, which is why talking about the mental and emotional roadblocks of entrepreneurship should not be taboo.

This article covers five of the common mental hurdles experienced by entrepreneurs—and reveals what you can do about them while trying to start and grow your own business.

Table of Contents

Launching a new business can be scary
Entrepreneurship can be lonely
Entrepreneurship is non-linear
Burnout is real
Rejection is not an option, it’s a certainty
Launching a new business can be scary

Putting your hard work into the world is nerve-racking, especially when you’ve taken so much time to build and refine. For many entrepreneurs, it can be a major challenge to simply conduct market research.

Putting your hard work into the world is nerve-racking, especially when you’ve taken so much time to build and refine. You put many hours into building a brand, finding a product, packaging, setting a shipping strategy, and finessing the look of a store to make sure everything is perfect.

Launching a business comes with a whole new set of challenges—all different from the ideation or scaling stages.
And of course, self-doubt. What if no one notices your launch? Or what if they do—what will they think? What if something goes wrong during the process?

These are all valid and normal fears. Shopify has seen many new business owners experience the same jitters before making that final click to go live. Take this future-preneur, for example, who called in to chat with our Support team about the upcoming launch of his online store (voice altered for privacy and confidentiality reasons).

How to cope with the pre-launch jitters
It’s normal to second guess and question yourself leading up to the big moment. But many founders can attest to the importance of getting started as a needed point of momentum for their entrepreneurial journey to take off. After all, the only thing worse than an imperfect launch is not launching at all. Rest assured, no one gets it right on the first try. Cracking the code of business growth is something you have to learn.

The only thing worse than an imperfect launch is not launching at all.
Instead, try using an imperfect launch to your advantage. Take Ryan Zagata of Brooklyn Bicycle Company, for example, who wanted to get his bikes in front of customers as soon as he could to use his learnings for improved, updated products and distribution infrastructure.

“We wanted to get to market as quickly as possible, and our way of getting to market was going to these bike shops, taking that feedback, and putting it out there. After that, we’ve made boatloads of improvements based on customer feedback. My advice would be: Acknowledge that, somewhere along the line, you’re going to put a better product out there. By marrying yourself to your original product and thinking that’s going to be the end of the world, that’s a losing proposition,” he says.

Entrepreneurship can be lonely
When Dave Linton dreamt up the idea for his bag business, Madlug, he had a budget of £500 (about $700) and no background in business. Being from a small town in Northern Ireland that was known for its love of a thrifty discount deal, his friends didn’t think a bag business was a good idea.

Though these initial circumstances may have made Madlug an underdog, Dave’s mission made it hard to quit: for every bag purchased, Madlug donates one to a child in the UK foster care system who would otherwise have to carry their belongings in garbage bags. “I’ve always been passionate about championing and representing the underdog. That’s why I got up every morning,” Dave says.

And so, Dave played the long game. It took him a while to get cash flow management under control, but it was eventually worth it, as that £500 investment turned into £500,000 in revenue six years later. But he remembers many dull, sad, and scary moments that made it hard to keep going. At one point, he found his business cash flow stagnating at a few hundred dollars per month, leaving him helpless and lonely. As a solopreneur surrounded by people who didn’t share his entrepreneurial mindset, he found he had no one to turn to; no business partners or trusted mentors to run ideas or big decisions by. The entrepreneurs’ struggle was very real.

Dave Linton and members of his team pose with a newly fulfilled order shipment outside the Madlug office in Northern Ireland.
Dave Linton and members of his team outside the Madlug office in Northern Ireland.
How to combat loneliness
Working in isolation, can easily become an entrepreneur’s norm. Technology means you can run your entrepreneurial venture without ever leaving your desk or even changing out of your sweatpants. And many entrepreneurs don’t know where to turn to for support (especially solopreneurs like Dave), so they either forge on without a professional network to lean on, or have to build a network while they also build their business.

Similar to what Dave was craving in Madlug’s early days, it’s equally important to surround yourself with people who support your business and your lifestyle. Building community—or joining existing ones—is key to building a better set of resources and connections that will come in very handy when scaling a business, especially in times of isolation. For Dave, it was through his own networking that he eventually built a team of trusted advisers and hired a business coach to help him with Madlug’s key decisions. “I have the support of a board who are nearly more courageous than me,” he says.

Entrepreneurship is non-linear
Fasten those seatbelts: the ride of entrepreneurship comes with ups and downs—many of them. From unexpected logistics problems to sourcing, staffing, financing, and quality issues, you never know what challenges a new day will bring.

When Janna and Shira started Flourist, selling premium quality, traceable grains and beans, and freshly milled flour, they didn’t anticipate so many uphill battles. In the early days, they shipped their goods on Greyhound buses, hand-sewed packaging bags, and went through never-ending hoops before getting their business permits.

Sometimes the lows feel like the whole world is conspiring to keep you from succeeding.

Janna Bishop, Co-Founder & CEO of Flourist
“It could be little, like our mixer breaking the week before Christmas, or a whole batch of bread not working out, or it could be major like the city revoking our occupancy permit on the day we opened our bakery over one missing check mark on a form,” Janna adds. They admit that the highs and lows take a toll on their mental health, typically manifesting in stress or sleepless nights.

How to build resilience
While entrepreneurship may always be fraught with uncertainty, the early stages of starting a business are likely to come with more lows than highs. It’s important to persevere through those bumps, as they typically entail solving foundational problems that are key to getting your business up and running, like figuring out complicated logistics, finding the right suppliers, and hiring employees. Getting those early, hard problems right will pay dividends in the long run.

For Janna and Shira, sourcing and shipping their products are problems of the past. But they’ve learned to expect that other lows are bound to show up just as much as the highs. Luckily, the larger their business gets, the more things steady out. Janna remembers reading a quote recently that said, “How do we build endurance? We endure.” “I think that’s just it. You just need something, anything, to get you to the next step,” she says.

Flourist founders Janna Bishop and Shira McDermott at their warehouse in Vancouver, Canada.
Natalie Gill of Native Poppy knows the importance of resilience, too. When she started her flower business, she drained her savings, plunged into debt, suffered staff shortages, and experienced failed expansion attempts that impacted her health, sleep, and personal relationships.

“There are good days and there are bad days, and to get to where you want to go, you’ve got to climb through a lot of shit piles to get there. It’s not glamorous,” Natalie says.

To be able to grow, you have to be okay with being uncomfortable. And I’m uncomfortable all the time. But it’s fulfilling in a way that no other job has ever been to me.

Burnout is real
From marketing to social media, customer support, web design, packaging and fulfillment, entrepreneurs wear many hats. This, along with having the ability to access your business 24 hours a day, often comes with a packed schedule and poor work/life balance. To top it off, entrepreneurs are typically operating with extra financial or logistical pressures compared to more established businesses.

When that’s your reality, it can be easy to slip into unhealthy habits that involve neglecting your physical and mental health, not eating well, or not resting enough. Dawna Simon of Pink Peppercorn Apothecary shares her story.

How to nurture yourself and your business
Many entrepreneurs like Dawna know firsthand that in the thick of building a business, you can easily forget to nurture yourself. Whether or not we fulfill our basic needs—movement, food, sleep, and human interaction—adds up, eventually impacting how we mentally, emotionally, and physically handle the demands of running a business.

Investing in your wellbeing is just as important as investing in your business. Try a time-management tool to keep your life on track, lower stress, and improve work-life balance.

Rejection is not an option, it’s a certainty
For Denise Woodard of Partake Foods, hearing “no” is an all too familiar response.

“I spent hundreds of dollars and failed horribly,” Denise Woodard said, remembering her early days experimenting with food recipes out of her kitchen. Motivated by her daughter who suffered various allergies, Denise’s goal was to make tasty snacks that were healthy, natural, and free of the top eight allergen foods.

Denise Woodard faced over 80 rejections from investors before getting her business off the ground.
Then came the pleading with allergen-free facilities to give her small operation a shot at partnership—something they were not keen on unless they were manufacturing for a big, established business. With perseverance, she eventually had a winning recipe, a product, and a brand. She remembers driving around to natural food stores in New Jersey and New York every morning with a sell sheet, book bag, and samples to get them to carry it. Even then, the no’s she experienced up until that point were few compared to the ones that followed in the capital raising stage.

For many entrepreneurs, rejection is not just an early stage phenomenon. Entrepreneurs rely on the partnership and persuasion of others at every step to make their business a success. Whether it’s from buyers, wholesale clients, investors, suppliers, or social media, rejection can happen every day, in small and large ways that are difficult to avoid. Their impact can be psychologically taxing, often diminishing motivation, self-worth, and confident decision-making.

How to use rejection as fuel for motivation
There’s no escaping rejection—it will happen—but you can prepare for it. Shift your mindset to acknowledge that rejection is not the end of the road, but rather a key learning opportunity. Research from Carole Dweck, author of Mindset: The New Psychology of Success, supports the notion that those with a growth mindset—people who believe that abilities can be developed and mistakes can be learned from—are more likely to flourish compared to those with a fixed mindset. Those who believe their skills are locked in and cannot change are typically less adaptable to the pivots required in entrepreneurship.

Denise knows the importance of this. For her, “no” means “not now.” She is the type to laser focus on her next step and not let distractions—like no’s—get in the way.

Feedback is a gift. Use every piece of constructive criticism as a reminder that there is room to grow, goals to crush, and opportunities to better your approach for next time.

No one said it would be easy. But it’s worth it.
Entrepreneurship may be the road less traveled, but sometimes the rougher the journey, the more worthy the adventure. Whether you’re in the idea stage or scaling a business, cherish every small win along the way—they’ll make your journey worthwhile.

Just ask Jaime Garrastazu, who took a risk and quit a stable job to start Pompeii, a shoe and apparel brand, with four friends from college.

“It was the best decision of my life,” he says. “And not because Pompeii has been successful—I think success is pretty subjective—but because it’s impossible to think that any other career or profession could’ve given me this level of personal and professional growth.”

Remember to anticipate, prepare, take care of yourself, build your network, and develop a healthy mindset as you go. Every hurdle you overcome is good practice for more complex challenges down the road. An entrepreneur’s life can be incredibly difficult but oh so rewarding.

High levels of stress
Struggling to find product market fit and finding customers
Overworking and becoming burned out
Lack of cash flow
Finding the right business model
How can you overcome the challenges of growing a small business?
Growing a small business can be incredibly challenging. One of the best ways to overcome the challenges of entrepreneurship is by learning from those who have walked down your path before. Surrounding yourself with a great team and understanding the challenges faced by entrepreneurs can really help you get ahead.

How can entrepreneurs deal with loneliness?
Don’t be afraid to ask for help. Surround yourself with good people, whether that’s people you hire or your mentors. Knowing you aren’t alone is an incredibly important factor in dealing with loneliness.

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