10 Signs that you are a stressed-out, overworked, and underachieving entrepreneur

There’s no doubt about it, SME entrepreneurs, business leaders, and owners are remarkable individuals.

Against all odds, you create organisations that ultimately become the backbone of global economies. Often fuelled by a personal idea, you innovate with ambition, agility, and determination to change lives – your own, your employees, your families, and your customers.

Most entrepreneurs will create a business where they are at the centre of absolutely everything, and it feels like nothing can happen without their say so. This often leads to being pulled in many directions, working all hours, and sometimes even feeling trapped. 

Recognising the warning signs that you’re overworked

But it is still possible to regain that optimism and work to embracing the freedom of being your own boss. The first step is to recognise the tell-tale signs you’re overworked:

  • You are back to dreading Mondays, just like when you were in corporate.
  • Customers have become your enemy. Of course, you want to make sales but dealing with all their queries and complaints is more than irritating.
  • You’ve stopped going into the office. You receive hundreds of emails a day and feel overwhelmed by all the questions from your team.
  • You are working late into the night to keep on top of your admin and compliance.
  • You feel lonely and isolated. There’s no-one to turn to for advice. You can’t share your problems with your team, and you are working so much that work is the last thing your partner and family want to hear about.
  • You have physical symptoms – constant fatigue, trouble sleeping, headaches, illness.
  • You have become clumsy and are making mistakes which are just causing more work.
  • You have a short fuse at work, at home, and generally this has become your default demeanour.
  • You socialise less and even when you do, you aren’t fully present. In fact, you are always at work … even when you are not at work. You find it impossible to switch off and can’t remember the last time you took a whole day off, let alone had a holiday.
  • You’ve stopped exercising and doing the things you love which you thought you would have more time for when you started working for yourself …

If you are reading this, and you recognise these signs, don’t panic. Taking time to step back and acknowledge where you find yourself are the very first steps to making changes. And I’ve found it also helps, unfortunately, to know that you are not alone, most entrepreneurs find themselves here at one time or another.

How to stop wearing too many hats

The very nature of being an entrepreneur is that to start we have to do so much with limited resources, meaning we take on the hats of many roles. But to grow we must learn to free ourselves up to focus on what only we can do to expand our business. This is not a one-off exercise. Every few years throughout my 20-year journey from bootstrapped startup to global organisation I have managed to free myself up, only to find I am wearing multiple new hats as I start to focus on our next stage of growth. This is a key skill entrepreneurs need to master.

There are some brilliant strategies to help alleviate stress and enable you to fall back in love with your business.

Identify your secret sauce

Take time to understand your core competencies and what it is that only you can do in your business which is critical for its success. Focus your time here and consider outsourcing or delegating everything else.

Prioritise and delegate or outsource

Make a list of all the tasks and activities you are responsible for and categorise them by importance and urgency. Delegate or outsource those that are less critical and time-consuming to free yourself up for the strategic and value-adding work. And for those tasks that are not important or urgent, question whether they need to be done at all.

Get the right people around you

Take on employees or contractors to support you and share responsibilities. I recommend working with an EA early on, even if part-time. This person can shoulder a lot of the admin burden and help you manage your time to stay focused. In addition, as you grow, fractional C-suite support is affordable and invaluable to mentor, advise, and lead specific business-critical functions which are outside your area of expertise.

Automate and streamline

Use technology as much as possible to automate repetitive and non-core tasks and help you scale.

Set boundaries to manage your time

Use your EA to support here. Ask yourself if new tasks and commitments align with your business goals and if not, learn to say no.

Seek out an entrepreneurial community for mentorship, advice, and a friendly ear

Connect with other experienced entrepreneurs and mentors who can provide guidance, problem solving insights, and help you build a valuable and supportive network.

Continuously evaluate and course correct

This is a never-ending process. Set aside time every few months to review what’s going well and what’s not. Are you spending your time where you should be? And are you wearing the right hats? Be willing to let go of tasks that no longer serve your needs.

And lastly, I encourage you to introduce a new KPI, your happiness factor, and measure it regularly. It’s the one that really matters!