I love to write about the genuine struggles of being an entrepreneur, even more so than talking about success. I think its important to give the full and honest picture of what it’s like to those embarking on this adventure, and to help those who are feeling similar emotions to realise they are not alone.

If this article resonates with you, please leave me a comment below – I’d love to hear from you. Perhaps you have another lesson you’ve found hard to learn?

These are the hardest lessons I personally experienced, and although thankfully I feel less affected by them now they were incredibly difficult times to battle through.

Success won’t make you happy

Yes, that success you’re working towards might not actually make you happy and it was a very hard lesson for me to learn!

It became very apparent to me a year into being a business owner that I wasn’t happy, despite having built a 6 figure business and achieved everything that I wanted to do (and more). I was flabbergasted! All that success and all I felt was utterly miserable. After a lot of deep reflection I realised that I was doing far less of what I loved and this made me feel unfulfilled and very confused about how to progress. A mentor of mine helped me to identify that my new goal was to build a business that allowed me to not only do more of the high level activities that was required to grow the business, but to do build in doing more of what I truly enjoyed.

You’re going to lose friends

I think we all experience a shift in our circles of friends at some stage, but no circle shifted more for me than when I started my business. I found I had less in common with many friends as I found I was more driven to spend a weekend at home learning new business skills, then going out for wine and lunch. Some friends couldn’t understand the sacrifices required to make a business work, some felt that I had moved onto a stage of my life that they no longer related to and sadly a rare few were jealous of the success I was having. Of all the hard lessons I learned, this was perhaps the hardest one but it became a blessing when I realised I was surrounded only by positive people who wanted to see me succeed.

That freedom you wanted is now even farther away

I think so many are experiencing this one! We start our businesses with the idea of escaping the corporate world we hate so much and to have more time and freedom to do what we want. What happens for most is the quick realisation that time off becomes a thing of the past. When things go wrong in our businesses the buck stops at us – there’s no one to escalate issues to, and for most starting out there’s no team to help solve problems and this often affects the time we hold most precious – evenings, weekends and holidays. Cue disgruntled spouse, friends, family and feelings of guilt!

For me, these were the hardest lessons I learned for sure! The practice of daily reflection and honest conversation with mentors has helped me to identify areas I’m not happy with, and to build a future plan for more happiness. What has always struck me about being a true entrepreneur is that despite the tough aspects, I wouldn’t have it any other way and this is a common thread that runs through conversations I have with others. We are a strange breed!



Oh Laura this really resonated with me this morning. Of so true – especially when it comes to friends, but the good thing is that I feel like i have made so many more new friendships since I started this journey. o))


Doesn’t being surrounded by AMAZING people feel great Caroline? 🙂


Another great post love your work. All so true


Thank you so much Chris! Glad you’re enjoying my blog posts 🙂


I’m totally with you on these!


For me, it’s feeling isolated because I’m the only one doing this out of everyone I know. I have to go online to find my tribe of entrepreneurs who get it and that I can discuss those heartfelt struggles. Also, the investment in myself. At first, I thought I could do it all myself but then I realized I needed to take training courses, find a coach and invest in software to get things going. It’s making things tight and stressful but it will be worth every penny in the end. I also wouldn’t have it any other way =) When things start coming together, it’s so exciting!!


Marie, I think every entrepreneur I know has to go online to find their tribe. I live in a small town, and its just not the “done thing” here. You can do this! 🙂


Totally agree.

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