Are you ready to be your own boss?

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Have you ever dreamed of running things YOUR way?


Or imagined designing your working day to suit your strengths, energy flow and personality?

Have you longed to flex time away from work when you need it – school concerts, sick children, parent emergencies, root canal, a surprisingly sunny day? 

Do you know that freedom and authenticity are amongst your highest values and you’re wondering how you can possibly express these fully in your working life? 

At some point in your career, the chances are you will have toyed with the idea of going it alone – as a freelancer, independent or solopreneur. But something stopped you from taking it seriously - perhaps the need for financial security, a doubt in your ability to set your own goals or develop a strong business strategy, or an inability to settle on the ONE idea that you’re ready to commit your whole self to. 

Maybe you’re giving it some serious thought right now. What does having your own business really offer? What are some of the skills, mindsets and qualities you’ll need to succeed?



A quick Solopreneur Pulse Check



Try my ‘Could I be My Own Boss?’ checklist.  You can request it here.


How many of these items can you tick off with confidence? The truth is that you’ll need all these – and probably more. There will be many other things to consider of course – do you have a viable business idea? Is there a need? Do you have the resources? Why does this matter to you?

 My experiences of having my own business and the reasons for launching each of them have varied over the years! As owner of Freestyle Careers, I have 100% enjoyed the freedom of setting my annual, monthly, weekly and daily strategy, tactics and practices. I’ve embraced with great relish, the opportunity to express myself through this business, to honour my values in how I work and with whom. For me, this is worth celebrating daily because I know I’m doing work that matters deeply to me.

 On the down side, the business challenges of building a service people want, of managing a regular flow of clients and of having the discipline to focus on the less glamorous and more mundane tasks, have stretched me at times! 


8 Questions to ask before you jump

 If you’ve never been your own boss before, there’s no doubt that this is a big change from your life as an employee. It’s worth some focused time and targeted questions. But is it a case of ‘not knowing what you don’t know’?

Here are 8 crucial questions to ask before you jump:


1. Why do you want to have your own business?

What do you hope it will give you?


2. Do you know what being a business owner really involves?

Have you spoken to anyone in a similar business to the one you’re planning?


3. Do you have the skills, mindsets and personal attributes to weather the ups and downs of business life? (Request my checklist)

Will you show up and put in the hours even when things are not flowing as you hoped? Can you rely on yourself?


4. Do you know what financial foundation you need to see you through set up and the first year or so as your business gets established?


5. Are you more attracted to a) running your own business or b) escaping your present employment?

You need passion, eyes-wide-open commitment, flexibility and resourcefulness to run your own business – wanting to escape a job you’re out of love with won’t be enough.


6. Are you GREAT at looking after yourself, setting boundaries, refueling regularly, nourishing yourself?

You’ll need super self-care abilities when you’re a solopreneur.


7. Do you have a mentor, coach, or savvy business supporter who will share their expert eyes, encourage you to ask the difficult questions, then find the best answers?


8. Are you ready to get uncomfortable?

An ability to stretch your comfort zone – often – is a pre-requisite. Work won’t come flowing in without strategies and actions that stretch you to become more visible- which for many means getting uncomfortable.




And 4 to go deeper


By now, you’ll be in full explorer mode!

To go even deeper – and get into action - at the bottom of the checklist you’ll see 4 important questions. 

These require some deeper thought. I suggest you take them into your journal, be honest and write down everything that comes up for each of them.


What will being your own boss give you? 

This is your WHY and is vital. It will reveal whether you’re just jumping ship or actually jumping towards something meaningful for you.


What are your fears? 

Write them down. Are they real or imaginary what ifs?


What do you need? 

What’s holding you back? Information? Self-belief? Fears? Timing?


What next?

Write a list of actions you can take to move yourself towards a decision. Start with one you can do today. Give the others a deadline.


You’ve now spent at least 30 minutes thinking seriously about being your own boss.

Is it for you?


If you’d like to explore this option more deeply, get crystal clear about WHY this matters and is a good option for you, get in touch today.  Don’t let imaginary demons stop you from exploring this option or from understanding what success on your own terms really means!