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The 10 biggest mistakes I've made on my entrepreneurial journey

entrepreneur mistakes strategy values May 21, 2024

As an entrepreneur, I’m constantly reflecting, analysing and iterating what I do. Be that the services I offer, the ways I engage my clients, my messaging and pricing. This month, I’ve been looking over what I’ve done well and what I’ve tripped over on my journey and need to avoid in the future. And in doing so, I’ve also done some research on how “typical” my mistakes are compared to other female entrepreneurs. It made interesting reading – so I thought I’d share it with you.

But first, let’s dive into my self-critique


In the two years of being an entrepreneur I made the mistakes of getting:

  1. over excited early on and charging off without fully assessing my service propositions
  2. sucked into the social media rollercoaster, wasting precious time chasing likes and not telling people in my immediate network what I was doing
  3. distracted by all the shiny tech I could incorporate into my business rather than thinking about the end to end experience from a client perspective
  4. ignoring the data I had in my business, especially my CRM / list data, and what it was telling me
  5. worked up that other people were doing what I was doing, but not doing a great job (no imposter syndrome here)
  6. into the habit of breaking good habits – working too late, not exercising enough for a start
  7. out there too little and not making the most of networking opportunities
  8. stuck into the detail of the work “farming”…and not making enough time “hunting” for new clients
  9. complacent about admin, and then getting overwhelmed when I finally got to it
  10. wrapped up in making my website all singing all dancing…which actually just made it all complicated.


When I look at this list I can boil it down into:

  • Not spending enough time considering what I was doing, and how I was going to do it better than or differently from my (many) competitors
  • Spending time understanding where my dream clients were hanging out (networking events not social media)
  • Being too focused on the product, not the promise. My clients don’t care too hoots about the bells and whistles on my platform, it’s more about the 1-2-1 connection and support
  • Not looking after myself enough – too much office face time, complicating things, and not enough time practicing self-care and kindness to myself (reasons I left the corporate world in the first place!)


All of these things are easy to fix:

  • I’ve refined my services down from 7 to 1 plus a couple of add ons.
  • I set my self targets on how many networking events, follow ups and meetings I have to make sure I’m getting out and hanging out with my dream clients
  • I’ve paired back my tech to the bare essentials – website and calendly.
  • Starting each day with exercise / self-care and not beating myself up for not getting into the office at 9am each morning.


Now. What was interesting was when I did some research into what common mistakes female entrepreneurs made in their first two years (OK when I say research I mean I asked Chat GPT) . And then I asked it what mistakes entrepreneurs made in general. And then I asked it what the boys failed at.

AND GUESS WHAT…It didn’t have an answer for the boys. So, I told ChatGPT that it was sexist, and it hastily found me a list of mistakes that male entrepreneurs make too. So here are those lists:

Female Entrepreneurs

All Entrepreneurs

Male Entrepreneurs

Underestimating themselves

Lack of resilience


Lack of self-promotion

Ignoring feedback

Reluctance to seek help

Fear of failure

Failure to pivot

Resistance to change

Limited access to funding

Lack of market research


Not seeking mentorship

Lack of focus

Emotional intelligence

Ignoring networking opportunities

Ineffective marketing

Communication style


Poor hiring decisions

Lack of diversity


Overlooking legal & regulatory compliances


Not negotiating effectively

Ignoring technology trends

Risk Taking behaviour

Failure to delegate


Difficulty delegating

Work life balance


Work Life balance


Poor Financial Management


 (Items in BOLD and mistakes I've made)

WOW, I found this so interesting why? Because when you look at the mistakes that entrepreneurs make in general, most of the mistakes are about making bad decisions, missing something important or doing something badly.

But when you look at what’s holding female entrepreneurs back, a lot of it is mindset – it’s the fear of failure, the perfectionism, not getting out there telling people what they are doing and how well they are doing. Essentially, it all boils down to playing it safe and small because of fear – fear of failing, talking to others at networking, of being perceived as arrogant when we talk of successes (which we kind of need to do when we sell our services and our products right?)

And then let’s look at the male list. No imposter syndrome here…just some brash, over confident, poorly communicating, risk taking competitive dudes landing badly with their customers. Nice.

Now what struck me here, is that in the female list, we’re getting in our own way and tripping ourselves up with fear and self-doubt. The men however, are getting out there, not worried about how they are perceived (or communication style and EQ wouldn’t be on the list!) and forging ahead. In fact many of the “mistakes” or challenges that trip them up, are actually found in the top 5 traits that drive success in male entrepreneurs.

 Do you want to see those lists of what drives success? Of course you do




Resilience & Adaptability

Passion and purpose

Confidence & Risk taking

Collaboration & networking

Adaptability & innovation

Competitiveness and drive

Emotional intelligence

Effective leadership & team building

Visionary leadership

Innovation and creativity

Strategic planning & execution

Technical expertise

Community engagement

Resilience & persistence

Networking & Strategic partnerships


Yep, I was right! Many of those same traits are on the list…Confidence, risk taking, competitiveness. So, when men “fail” they are actually doing the "right" things, just some of them are doing them badly, or going too far. While us girls are generally doing all the right things, but getting in our own way. Interesting huh.

My final reflection when I look at my list of mistakes is that yep, my experience is pretty typical. I’ve definitely made a number of “general” mistakes, and I’ve definitely tripped myself up a few times, particularly on networking and self-promotion. But now I've got this self-awareness, particularly on the latter, i'm going making a conscious effort to not self-sabotage. So going forward I'm: 

  • Regularly evaluating what went well, what didn’t and being honest about what’s not going right / what mistakes I’ve made – failing fast and fixing as I go
  • Surrounding myself with cheerleaders, friends and collaborators who support, champion and celebrate me and the success I have achieved
  • Getting my own mentor who helps me step back, see the big picture and focus on what’s important as I go. 

I’d love to hear your thoughts about what you struggle with and if you’re up for it a chat about how I could support and mentor you on your journey – making sure that you don’t get in your own way or making the same mistakes I did!  

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