11 Struggles These Entrepreneurs Faced (and How They Overcame Them)

Success is often not a straight line; it’s full of ups, downs and plenty of surprises. In entrepreneurship, the path to success comes with obstacles you’ll need to overcome if you want to continue on. Many entrepreneurs share similar obstacles, and some may be more unique to specific situations or people. However, when all is said and done, it’s the way an entrepreneur solves each problem that can serve as a guide for others to solve their own.

Below, 11 members of Rolling Stone Culture Council each share one major struggle they’ve faced as an entrepreneur, the steps they took to overcome it and how other entrepreneurs might learn from their journey. 

Scaling Our First Ticketing Business

One big struggle I faced as an entrepreneur was scaling our first ticketing business. We overcame this by implementing structured processes, leveraging technology for efficiency and building a strong team with clear roles. Other entrepreneurs can tackle similar challenges by focusing on process optimization, investing in scalable tech and ensuring effective team collaboration. – Francis Hellyer, London Theatre Direct

Charging Full Price in a Struggling Economy

One significant struggle I’ve faced is feeling guilty about invoicing full amounts after I’ve developed friendships with clients and then see them cutting costs. While I genuinely want to support them, it’s crucial to remember that providing my best services is invaluable. It’s important to set clear boundaries from the start, and stick to them. – Brianne Dezzutti, Higher Collective

Balancing Entrepreneurship With My Personal Life

One big struggle I’ve faced as an entrepreneur is finding harmony between family, friends and my hobbies while managing the all-consuming demands of entrepreneurship. I prioritize time management and set clear boundaries to overcome this, ensuring dedicated time for loved ones and personal interests. Accountability partners are crucial, calling me out when I am out of alignment with my goals. – Rhett Power, Accountability Inc.

Lacking Confidence as a Leader

One big struggle I once faced as an entrepreneur was lacking confidence. But, I kept working hard and believing in myself, and, sure enough, I took my public relations firm to new heights. I tell everyone to surround themselves with good people and good clients who lift you up. The result: pure magic. Always remember that you are amazing! – Paul Fitzgerald, Salt & Pepper Media Inc.

Gaining Respect as a Woman in Tech

Being taken seriously as a woman in tech was a big challenge. I overcame it by demonstrating expertise, building a strong network and continuously improving my skills. For others, focus on showcasing achievements, seeking mentors and staying resilient. – Jessica Billingsley, Sona Capital

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Checking My Emotional Connection to My Work

When you’re an entrepreneur, it’s really important to strike a balance with emotional connection to the work. I don’t believe work isn’t personal — it is. It reflects time, effort and, hopefully, heart. But, understand that if a person or brand doesn’t buy in, that’s their prerogative, and it’s OK. You and your ideas will be right for someone else, at the right time. – Sarah Jenkins, The Romans New York

Carving Out Space in an Established Market

One of many struggles I faced was taking our product, Blind Tiger, and working to break into a market traditionally dominated by alcoholic beverages. At the onset (and even today) we had to convince consumers of the value and appeal of non-alcoholic options. The challenge was not only in product acceptance but also in securing shelf space. – Rebecca Styn, Blind Tiger, Inc.

Failing Slowly

Failure as an entrepreneur is inevitable. Failing slowly is a gut punch to any business and the biggest struggle I faced in the past. I think if we can fail faster, we can expedite what needs to be adjusted and grow stronger in our individual efforts. If we learn to identify the problems quicker while not being afraid to fail, we create strength and generate growth. Fail faster. Grow stronger. – Josiah Corbin, Elite Multimedia Productions

Generating Revenue and Profits

As someone who has bootstrapped a company, I understand the uphill battle toward generating revenue and profits. To get a business off the ground, you need to develop services and product offerings that benefit customers and are worth their investment. We’ve had to be efficient in our decision-making to guarantee a product-market fit. – Dustin Eide, CanPay

Knowing When to Pivot

Knowing when, how and in what direction to pivot is an age-old struggle. Empowering a core team to share their strongest views with open hearts and without fear has proven invaluable. Whether a board, business partner, leadership team, “kitchen cabinet” or other network, lean in to asking for help from those who have gone before, have keen insight and will speak truth in service of your cause. – Scott Curran, Beyond Advisers

Allowing Time to Pause and Regroup

Many leaders expand on multiple ventures at a time, which means workload, personal tasks and professional duties add up as fast as innovative ideas. Taking even a tiny part of the day to pause and let yourself regroup is simply vital to giving the brain ample time to address and strategize about the problem of not having enough time. – Andy Hale, Hale & Monico