6 Unexpected Challenges of Entrepreneurship

February 14, 2024

When people discuss the challenges you face as an entrepreneur, they usually refer to cash flow issues, hiring and firing challenges, growing pains, having a plan (or the lack of). But that is NOT what this episode is about. We rarely discuss the unexpected challenges of entrepreneurship that play on a much more human and personal level.


Don’t just sit there waiting for the light to go green.

No idea what I’m talking about?

Maybe you’re one of the many people who have a secret dream of doing business your way. Thinking about it, dreaming about it. But do you dare to pursue it, because… the sensible thing is a 9 to 5 job? Paid by a boss.

For a while, Kate McGregor was that person. Then she decided she was done waiting for the right time, the right opportunity, the right whatever,…

She had the vision, found the guts, went for it and she pulled it off. She was her own green light.

Was it a 1,2,3 and done?

Heck, no.

It took a lot of grit, sleepless nights, tears, doubts, determination, and focus.

Fair to say, the many very human but unexpected challenges of entrepreneurship are foreign to no-one. Especially not to us, women heading a service business.

Yet so often they remain undiscussed.

Meet Kate McGregor

So,… Kate McGregor from NZ Out of Office.

Kate nails the art of combining business with pleasure. Her desk only keeps her excited for so long when exotic places loom. With Kajabi as her loyal companion, 6 months on home soil and 6 months elsewhere with a warm climate is Kate’s modus operandi.

For those not entirely familiar, Kajabi is an online learning management system with all the wraparound services on one platform. It’s the bees' knees for anybody providing online learning, coaching and online communities.

Kate offers Kajabi done-for-you services, but she also has consulting services where she helps people set up and run it themselves.

But it’s what led her to this point that makes for fascinating conversation.

Because being your own green light doesn’t come without its hurdles. The journey towards doing Business Your Way is riddled with a multitude of unexpected challenges of entrepreneurship.

Many of which I recognise.

So it’s time we have an open conversation about the human aspect of going down the business ownership road.

Challenges Of Being A Small Business Owner That Aren’t Often Talked About

Kate is a prime example of a female service based business owner who is determined to do business her own way. The underdog is her hero, the unconventional her goal.

But it doesn’t mean her journey has been free of challenges.

So, I figured, today was a good time to explore 6 challenges of being a small business owner that aren’t often talked about.

1. Unexpected Challenges Of Entrepreneurship: Transitioning Your Business Is Part Of The Journey

Interestingly, Kate’s business had a name before it had a purpose.

The initial idea in 2017 was that Kate and a flatmate would open a cafe where people could come and work together. Until the penny dropped it would also mean getting out of bed to make coffee before everyone else turned up. Idea canned.

Instead, Out of Office became a business in network marketing.

Which morphed into helping people with social media organic marketing

And then became a virtual assistant type business during the pandemic.

After which Kate niched-down to offering services in Kajabi.

But all along this journey, the mission was always the same: to have the flexibility to escape the office and live the travel dream. That was the plan.

Everything else worked towards that goal.

The lesson in Kate’s story:
👉 It’s unlikely your initial idea is the final version of what your business will look like. It’s simply one of the unexpected struggles of an entrepreneur.
Be prepared to go with what feels right and gives you the clients and the lifestyle you crave. Keep the goal centre stage. Pivoting and fine-tuning are part of the process.

2. Unexpected Challenges Of Entrepreneurship: Dealing With Imposter Syndrome And Self-Doubt

Kate used to be what she calls “a typical Kiwi”. Down to earth, with little self-belief.

It wasn’t until she attended a retreat hosted by her gym instructor that she realised she was her own biggest enemy (Talking about the mother of all barriers of entrepreneurship!).

During the retreat Kate was asked to do “The Glass Walk”, in what was, looking back, quite a safe environment. It was optional too.

Kate instantly decided she didn’t have to prove anything to anyone. Also, she wasn’t going to do it. 😂 Yet, the coach talked her through the decision-making process.

THAT was the moment she realised how inhibiting the whole self-doubt problem was.

In the end, she walked across the glass successfully, but it was the trigger point to engage with a life coach. It proved to be a pivotal moment in her life, because that life coach became her biggest cheerleader.

Kate had many more occasions where she can pinpoint self-doubt almost got the better of her.

It’s not that long ago, she told her life coach, “the universe did that”. To which the life coach replied: “ No, the universe hasn't done that. You did it. The universe may have listened, but YOU DID IT!”

The lesson in Kate’s story:
👉 Think about what is stopping you from achieving your dream, and never let that thing be YOU.
👉 Understand, it’s all a big journey. You don’t have to have it all figured out or get it 100% all the time. Just take the next best step in the right direction.
👉 Also, don’t underestimate what a life coach can do in negotiating the barriers of entrepreneurship we impose on ourselves.

3. Unexpected Challenges Of Entrepreneurship: Dealing With Critics

But it’s not just the little voice inside your head you need to get in line. Often, it’s the people around you, who’ve known you since forever, who are your harshest critics.

When you go on a journey that involves different horizons, different perspectives and a lot of self-work, you don’t come out the same person you once were. Yet, Kate finds old colleagues, close friends and family don’t always keep up, … and are not afraid to voice their opinions.

To Kate, putting herself out there, as it is, is scary enough. But when people start voicing their doubts, their fears and show their lack of understanding, she finds herself at risk of losing sight of her guiding star. (She calls it her “North Star”.)

Her old LinkedIn contacts haven’t really moved on from her corporate days and are puzzled by the steps she takes. Likewise, family and friends seem taken aback that she got herself to the point of getting a mortgage, living her life the way she does. Because isn’t she just messing around, trying to shake that travel bug?

The lesson in Kate’s story:
👉 As an entrepreneur, the fear of being criticised and judged can be massive. But it’s one of the unexpected challenges of being a business owner that can really hold you back or even put you on the wrong track. You have to understand it’s part of the journey, but always remember YOU get to make the decisions in your life. Only you know what you're aiming for, your goal, your “North Star”. So make sure you also have the right support to balance out the critics.

4. Unexpected Challenges Of Entrepreneurship: Being Distracted By Shiny Objects

This is another unexpected challenge of being a business owner that isn’t much talked about.

Especially at the start of her journey, Kate faced what she now calls “The Shiny Object Syndrome”.

In a world that is full of gurus, she found it incredibly easy to get distracted by the promise of things that would make it happen overnight. With the online world louder than ever, everyone is trying to catch your attention with the quick fix, or the best platform, or the new whatever-it-is.

The reality is that every business is different and most of these shiny objects turn out to be nothing more than an unwelcome distraction.

As a starting business, there is very little you really need. As her business grew, Kate realised what mattered was finding the tools that enable her to work efficiently. She now (tries to) dedicate time to find that tool and then ignore the shiny object distraction until the time for reassessment arrives.

The lesson in Kate’s story:
👉 Financially, as a start-up, it makes sense to start with only what you need and do a lot of the work manually.(An Excel spreadsheet and an email account did the trick for Kate.) At an early stage in your business journey, it’s hard to justify the cost many of the expensive tools. Once you start to scale your business, you need to consider what tools are going to help manage your time better. (A project management tool, and Kajabi, if that’s suitable for your business. Kate also uses Canva and Xero.)
👉 Every year or so, reassess the tools you’re using. Go beyond the consideration of price. Consider the cost of moving platforms, retraining staff, and look for the best fit.
👉 Fact: There is no such thing as a magic wand. To stop you from getting distracted by all the shiny objects, put a stop to the free trials. Don’t attend all the free workshops. If you struggle with this unexpected challenge of being a business owner, get a business coach to keep you accountable.

5. Unexpected Challenges Of Entrepreneurship: Wearing All The Hats

These days, Kate only needs to focus on the Kajabi online learning management space, but once upon a time, she was doing all the jobs and had to be all over the many aspects of her business. It was a lot!

This is probably one of the more talked about barriers of entrepreneurship out of our list of 6.

Kate vividly remembers doing her first tax return, and she promised herself she would never do that again. So a bookkeeper was her first hire.

As her business grew, Kate added a contractor who helps her with the Kajabi work, and she also has a virtual assistant.

Kate is determined to keep her business manageable, but she learned certain things are better handed over, while she focuses on what she does best and what matters.

The lesson in Kate’s story:
👉 Focus on being the boss of your business and play to your strengths. Get in the experts for all the other bits sooner rather than later, so you can be the expert of your business.

6. Unexpected Challenges Of Entrepreneurship: Having To Fit Into A Box

As a digital nomad, it’s only logical Kate has a mix of Kiwi and International clients. Which doesn’t make for easy bookkeeping or straightforward work hours, for that matter.

But that’s only the superficial difference. Kate notices an apparent difference in Kiwi attitude versus that of an overseas business.

Kate notices that, in general, Kiwis have been reluctant to embrace the flexibility of online work. She noticed Kiwis also don’t shout about it when they do work remotely. It took the pandemic to make New Zealand catch up with the rest of the world.

It was a celebratory moment, because it meant she no longer had to explain remote work any longer.

That said, Kate still found that none of the boxes applied to her when she was filling in the census form or applying for her mortgage.

The lesson in Kate’s story:
👉 Although people’s minds these days have opened about the many ways you can earn a living, there are still times when you have to push back. Don’t be afraid to get outside of what is considered normal in society's expectations. Surround yourself with people living similar lives to yours to avoid feeling isolated in the unexpected struggles of an entrepreneur. They are out there, they just aren’t vocal about it, most of the time.

Kate’s 3 Pieces Of Advice

As I usually do, I finally asked Kate about her 3 top tips for business owners who are just starting out.

This is her reply:
✔ Get a business coach: Having the right support in your business is indispensable. Kate says she has had a business coach for five years. Having someone to keep you on track towards your “North Star” is golden.
✔ Invest in things to free up your time as your business grows into a full-time affair. Be that extra staff or tools. It’s too easy to get caught up in working all hours of the day if you’re not careful. Don’t be the victim of your own success.
✔ Learn the set boundaries: Coming from the corporate world, people pleasing and saying yes to everything will not help you in the long term. (It’s another one in the list of very human but often unexpected challenges of entrepreneurship.) Keep your eye on the “North Star” and reassess regularly. Also, “no” is not a swear word. 😉

Connect With Kate McGregor

Get in touch with Kate McGregor from NZ Out Of Office to discuss everything Kajabi.



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