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10 Unconventional Strategies for Overcoming Entrepreneurial Challenges

In this article, we delve into the unconventional strategies used by 10 successful entrepreneurs to overcome significant challenges in their journey. From early-stage founders to CEOs, these leaders share their unique experiences and recommendations, starting with embracing breaks during business downturns to organizing reverse-brainstorming sessions.

Dive in to discover these 10 insightful strategies.

Embrace Breaks During Business Downturns

Take a break and smell the roses!

One of the biggest challenges all entrepreneurs face is the downturns when attracting new clients or business comes to a standstill. Every business has peaks and valleys, but it’s the valleys that frighten us the most. This is the time when we must hold steady on our course and not divert from our mission.

When I have faced a long stretch of time landing no new clients, I find it extremely helpful to stop and pause before the frustration and fear overwhelm me. I will take a day off, or even several days, and simply do something that I love, like travel or fishing. I need to reset my mind and spirit by doing something I love or enjoy. Then, I can return to the task of climbing out of the valley, refreshed and infused with new enthusiasm.

It works every time.

Dirk Foster, Founder

Diversify and Maintain Consistency

One unconventional approach that has helped to overcome challenges on my entrepreneurial journey is the strategy of diversification, coupled with consistency. It might seem counterintuitive, but this combination has served as a compass guiding me through the rough seas of entrepreneurship.

Diversification involves trying different solutions to a problem. This process of exploration often highlights the path to an effective solution, even if it means wading through a few that don’t work. It’s like an iterative process, where each attempt, successful or not, brings us one step closer to the ultimate solution.

But diversification alone isn’t enough. It’s the consistency in this process that breeds success. By continuously learning from our past experiences and applying those insights to future decisions, we foster a culture of resilience and adaptability.

Rafael Sarim Özdemir, Founder and CEO, Zendog Labs


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Implement Reverse Mentoring

In our entrepreneurial voyage, “reverse mentoring” was an unconventional approach we utilized to overcome a significant obstacle. Instead of the conventional top-down approach to mentoring, we encouraged our intermediate team members to act as mentors to senior executives, including myself.

By doing so, we tapped into the innovative ideas, fresh perspectives, and technological savvy of our youthful talent. They provided insights that challenged our conventional ways of thinking and introduced a contemporary perspective to problem-solving. This approach not only nurtured a culture of collaboration but also empowered and motivated our junior employees.

The end result was a dynamic and adaptable organization that adopted innovation and responded swiftly to market shifts. Adopting reverse mentoring not only resolved the initial problem, but it also became a lasting practice, enriching our team’s diversity of thought and paving the way for perpetual development and success.

Michael Callahan, Founder and Director, The Callahan Law Firm

Utilize Unique Recruitment Strategies

Once, in my business, I needed to hire a specialist for a specific job. I tried to find this person on regular job sites, but it wasn’t working. So, I did something different. I looked up companies that had the specialist I needed and found out how to contact them. Then, I made a video. In this video, I explained the exciting project I was working on and why I thought they should join me to make it happen.

This unusual method really stood out to the potential employees. In the end, I hired the specialist I was looking for. This showed me that sometimes, you need to be daring to solve tough problems.

Martin Potocki, CEO, Jobera

Focus on Niche Communities

When starting a podcast production agency, the challenge of standing out in a saturated market is often faced. Instead of chasing big clients right away, focusing on niche communities and bringing an A-game to them can be a beneficial strategy. This approach taps into passionate audiences with specific interests, which helps gain momentum and credibility.

As growth occurs, word-of-mouth referrals play a significant role, and it’s possible to start working with big names like PepsiCo and Booking.com. Therefore, the recommendation would be to find a niche, deliver exceptional value from day one, and let satisfied customers become brand ambassadors. It’s an unconventional approach, but it has proven to work wonders, and continued success can be achieved by staying true to a unique podcasting formula.

Harry Morton, Founder, Lower Street

Keep Entrepreneurial Ventures Confidential

When I was first starting CultureAlly, I read everything I could about entrepreneurship. Over and over again, the same advice was given: that the key to success was to network, network, network. However, I did the absolute opposite. I didn’t tell anyone.

For the first year that I was self-employed, my own family thought I still had my old 9-5 job. The reason that I didn’t share the story of my fledgling company is because I was tired of the stereotypes I received as a female entrepreneur. Fielding questions like, “Do you even have revenue?” got tiring. It was like there was some unwritten expectation that I couldn’t hack it.

So, I kept my mission to myself. And I went out and built my company. A tech company. And now that I’m growing and working with incredible people, I am happy to share my story. And hopefully, future female entrepreneurs will get typecast a little less!

Ashley Kelly, CEO and Co-Founder, CultureAlly

Integrate Mental Health Techniques

One unconventional strategy I adopted as an entrepreneur was integrating mental health techniques, specifically for my work-life balance and productivity. I incorporated mindful meditation and deep-breathing exercises in between high-pressure tasks to ground myself. Instead of the usual coffee breaks, I sometimes opted for short nature walks, allowing the serenity and fresh air to clear my mind and sharpen my intuition.

Additionally, spending a few minutes visualizing positive outcomes before diving into challenging tasks helped me stay focused and attentive.

Bayu Prihandito, Psychology Expert, Life Coach, Founder, Life Architekture

Track Time to Manage Work

As an entrepreneur, you don’t need to track your working time, but I’ve found it a helpful tool to manage it wisely. I record every minute spent on tasks like email, admin, projects, business planning, and more so I can review it all and break down my days.

With everything recorded, I can see which tasks are eating up more of my time than they’re worth and focus my efforts to find alternative solutions. Sometimes, I use delegation to manage extra tasks, while at other times, I might find automated solutions or simply restructure my schedule for more effective workflows.

Time tracking gives you the data you need to make smarter decisions about the resource that sometimes seems the most limited – your time.

Marnix Broer, Co-Founder and CEO, Studocu

Consider Quitting as a Strategy

Until just a couple of years ago, I could never fathom quitting anything in my life. No matter what the obstacle was, I would just fight and fight until I overcame it—often at great personal expense.

Then one day, I watched a TED Talk on the power of quitting. In short, the thesis is this: sometimes it makes sense to quit. No matter how much pride we have, it just isn’t efficient to fight against major obstacles. Since then, I view quitting very differently.

You need to remove hubris from the decision-making process. Your time can often be spent more productively in other areas. Think about where you are going to get the greatest return on your inputs (namely, your time). Will it be from fighting tooth and nail for months to overcome an obstacle? Or from pivoting, identifying another ripe opportunity, and capitalizing on that? I think the latter.

So that’s why I say if you come across a significant challenge in your entrepreneurship journey, don’t be afraid to just quit.

John Ross, CEO, Test Prep Insight

Organize Reverse-Brainstorming Sessions

One unconventional strategy I employed to overcome a major challenge in my entrepreneurship journey was organizing a “reverse-brainstorming” session with my team. Instead of trying to come up with solutions directly, we intentionally identified ways to exacerbate the problem or make it worse.

This approach allowed us to uncover hidden assumptions, reframe the issue, and gain fresh perspectives on potential solutions. By understanding the problem’s root causes more deeply, we were able to devise innovative and effective strategies to address it, ultimately leading to a successful resolution and valuable learning experience for our team.

Brian Clark, Founder, United Medical Education

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