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12 Unexpected Challenges Entrepreneurs Overcame

What is one unexpected challenge you faced as an entrepreneur and how did you overcome it? 

To help you overcome unexpected challenges as an entrepreneur, we asked business leaders and founders this question for their best insights. From the business model not working to the difficulties of online networking, there are several unexpected challenges entrepreneurs faced and the ways they have overcome them.

Here are 12 unexpected challenges entrepreneurs overcame:

  • Business Model Wasn’t Working 
  • The Concept of Remote Work
  • Hard to Let Go and Delegate Tasks  
  • Hiring Top Talent 
  • Taking Financial Risks 
  • The Entrepreneurial Mindset
  • Creating the Right Team
  • Partnership Agreements 
  • Limited In-Store Purchases 
  • Whether to Give Resources to Clientel or Internal Operations  
  • Offering Attractive Benefits 
  • Online Networking 

Business Model Wasn’t Working 

Shortly after we started, it became clear to us that our model wasn’t going to work. The marketplace started to get more and more crowded and we weren’t capturing enough people’s attention, which was evidenced by our low subscription numbers. Instead of focusing on a direct-mail discount card system, we transitioned into a digital company. We went from relying on a more traditional model to becoming more like the Kayak of digital health. Not long after such a pivot, a completely different subscriber base started to take form. The shift worked. We were unafraid to scrap the old way of doing things and start something drastically different – and that’s because we refused to surrender to failure.

Chris Riley, USA Rx

The Concept of Remote Work

Having started my entrepreneurial journey in the early-2000s, the concept of remote work and remote employee management is something that I definitely didn’t expect to have to deal with. Now, more than 20 years later, technological advances have enabled the vast majority of my workforce to work from home.

Learning how to adapt my management style to remote workers was definitely a challenge, however, I ultimately found that the benefits of facilitating remote work far outweighed the downsides.

Establishing strong communication channels and workplace cultures (in spite of physical distance) are two things that helped me overcome the challenge of managing remote workers. Expanding out from generic email and encouraging more modern forms of communication, such as video calls and instant messaging threads, enabled better communication between colleagues. These platforms also served as the basis of virtual team building activities, which built and maintained workplace culture.

Teresha Aird,

Hard to Let Go and Delegate Tasks  

As a geeky techy person, I have a strong psychological need to control my environment, master my technology and be self-reliant. These are skills that serve me well as an individual contributor. But as a lifelong entrepreneur, I have to work constantly at letting go and delegating.

The book ‘Turn the Ship Around’ powerfully demonstrates the benefits of ‘stepping back so others can step forward’. As a reaction to reading that book and to the management coaching I have had, I am getting better at not trying to solve every problem, give an opinion on every question and spin every plate.

Matthew Stibbe, Articulate Marketing

Hiring Top Talent 

It was phenomenally difficult to hire a top-quality CTO for my startup due to the extremely competitive market for this talent. I struggled with this for months and conducted dozens of interviews with little success. In order to overcome the challenge, I made myself a commitment to find the right person within 30 days. With that self-imposed deadline, I hustled on the problem like I had no option but to succeed, looking everywhere for the right person. I followed every lead, posted the job everywhere I could find, read hundreds of resumes, and worked my network. Ultimately, I found my CTO within my deadline and he started last week. The lesson for me was that when something isn’t working organically, to set aggressive but achievable goals and work determinedly to meet them.

Ken Fichtler, Gaize

Taking Financial Risks 

I was completely unprepared for the difference between managing personal finances and my business finances. For my personal finances, I rarely feel confident enough to make a possibly risky purchase for something that won’t have an immediate return. When it came to my business finances, though, it was getting used to hiring a contractor, purchasing a new SaaS tool, or upgrading a subscription plan with no guarantee that it would actually make me more that often played out well for my business. Learning to take appropriate risks was something I had to adjust to for the success of my business.

Dylan Miller, DSM Story Forge

The Entrepreneurial Mindset

Being an entrepreneur is lonely and hard! You have to be your own cheerleader and keep a positive and growth mindset over a long time in order to be successful. 

Working on my mindset was an unexpected challenge that I am facing as an entrepreneur and I am overcoming it by working with a business coach to create objective measures for success for my business while also providing ongoing accountability. I also have an accountability pod of business owners at a similar stage and we share ideas and feedback on a weekly basis. Finally, I belong to several communities and we keep each other inspired and pumped up on a regular basis.   

In addition, some of the methods that I use personally to focus on my mindset include meditation, journaling, a daily gratitude practice and also celebrating my wins by writing down my accomplishments at the end of each day. These practices build confidence, positivity and momentum!

Jennifer Drago, Peak to Profit, LLC

Creating the Right Team

When you start your business, you may have a strong vision and clear ideas on how to get there. But, the bottom line is that you can’t do it all by yourself. Employing a team of competent individuals is a challenge, but it takes a load off and allows the leader to focus on the long-term goals and strategies to drive the business forward. At the end of the day, it’s crucial to build the right team, right off the bat, by finding employees who share your vision and values.

Marc Roca, 4WD Life

Partnership Agreements 

Being an entrepreneur takes bravery, innovation, resilience, and self-conviction.
When I first started my journey into entrepreneurialism, the unexpected challenge faced was knowing how to forge strategic collaboration with others. I learned the hard way that partnerships don’t work unless you have a clear agreement in place with who does what and the monetary side that goes with it. My advice as given to me after 3 attempted partnerships: don’t create partnerships and don’t take the advice just from a select few, talk to many and inform your own view on what you want to do in your business.

Joanna McCatty, Protoscience

Limited In-Store Purchases 

Our company is only four years old, so we were very new when the pandemic began. As a beauty brand, it was a huge hurdle that people suddenly were staying home and limiting their makeup purchases. We overcame it by pivoting early to stuck-at-home friendly content and how-to videos for people looking to teach themselves new skills.

By branding our product as something you needed even if you weren’t going out, we were able to stay afloat. It also taught us the value of remote work options, which we still take advantage of today.

Rachel Reid, Subtl Beauty

Whether to Give Resources to Clientel or Internal Operations  

Everyone is so focused on growing fast, in clients and revenue. My agency blew up over the past 3 years, going from one person to 30 people, handling 25+ projects worldwide.

But I didn’t know much about management, about systems, SOP’s and financials. And things started slipping. I overcame this by firing 3/4 of my clientele and investing in systems and processes. I decided to focus on the well-being of myself, my team members and my clients. This included open communication and managing expectations better.

I took a hit in revenue but ended up with a healthier, more purposeful business that’s growing steadily without destructing itself from within.

Bibi Lauri Raven, Bibibuzz

Offering Attractive Benefits 

As a fast-growing start-up firm of chartered surveyors, we were hit with the realization early on that we needed to offer more than we thought to stand out to potential employees. We’re competing with top surveying firms for talent, so that’s why we looked at offering more than the standard benefits for our surveyors, and ones which benefit our customers too. Our solution was to offer a unique training opportunity: drone pilot accreditation. This training gives each surveyor a unique skill they can use throughout their career, and also gives us a USP over other firms. Our employees love it!

James Brook, Novello Surveyors

Online Networking 

As an entrepreneur, you’ll have to send emails when networking online. While starting out, it can be challenging to know what to write. I learned to personalize emails and not just send out mass emails with one general and clumsy subject line with cliche opening lines. You get more responses if you act like someone that wants to learn from them and come up with offers they can’t resist.

Mike Stuzzi, online entrepreneur

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