There’s something freeing about admitting you have challenges, especially when you discover you’re not alone in experiencing them.

Like the time you were a new start-up and were about to launch a new product and woke up in a cold sweat in the night wondering if you’d included a piece of vital information in the Press release.

You then remembered that all was well and reflected that you were now an established organization and delegated this function. You then reflected on your continuing struggle with perfectionism and your ability to ask for support. This got me into thinking about challenges and problems faced by new Entrepreneurs and leaders. I asked some and from a small sample found these included, in no particular order:

1) Perfectionism

Whether you work in an organization or as a solopreneur, perfectionism is the enemy of both creativity and growth. We’ve all worked with people who set impossibly high standards for themselves. The problem is you can delay and delay a launch until you’ve missed an opportunity. When it comes to finding the right people, you’ll never find the perfect colleague.

2) Burnout

I may be expected this from Solopreneurs, who often get caught up in doing almost everything, but this came up right across the spectrum. One of the causes is perhaps linked to perfectionism, as nothing appears to be good enough. Working long hours, stress and illness all follow. This is perhaps the most dangerous of all the challenges as, if unchecked, the consequences can be fatal.

3) Asking for Support

The feedback seems to show an insecurity. It’s almost as though asking for support is akin to failure. Surely, the failure is in not having support systems in place. It’s hard to imagine someone reaching the top without being capable of having support systems in place.

4) Disillusionment

Disillusionment came up as a worry, not so much for the Leader or Entrepreneur themselves, but that those working for or with them may become disillusioned. The worry was again that if the entrepreneur or leader performed less than perfectly, those around them or working for them would become disillusioned.

5) They need to be challenged

After discussing burnout, asking for support and worrying about disillusionment, they could forgive you for thinking that entrepreneurs and leaders would want a quiet time. Far from it, universally, the plea was for more challenges, presumably to keep them on their toes.


These are just a few examples, but most entrepreneurs and leaders in business have a desperate will to succeed. What also appears to be common is the need for them to recognize their challenges and banana skins while getting support from wherever they can. As the saying goes, “It’s tough at the top” and what will make it harder is not getting all the support you need.

What do you think should be added to the list? Please let me know in the comments.

Carrie Jones