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Good news: You’re your own boss. Bad news: You’re your own boss.

Running your own business has plenty of ups and downs. The most obvious advantage is the opportunity to be your own boss. This can be fulfilling but it can also be challenging.

If you walked down the street and randomly asked passers-by if they would rather be an employee or their own boss, the overwhelming response would be in favour of the latter – but the vast majority never actually fulfil that dream.

Running your own business is not for everyone and I tell my clients that every business is a ‘family business’; every decision you make in relation to your business impacts your family in some way.

When I reflect on my own journey there are some definite pros and cons – and some days it is very easy to recognise and relish the pros, while on others, the cons can be all too apparent.


Choose the work you do

You get to follow your passion and do work your truly love. One of the happiest people I know is a fly-fishing guide. I caught up with him at the end of the trout season in New Zealand at the end of April. He had worked every day since the start of December including Christmas Day and New Year’s Day. And guess what we did when he finished the season? Yep, we went fly-fishing.

Work with who you want

You get to choose the people you spend your day with and create a culture and vibe in your business of your own design.

Work when you want

I had a pretty busy year recently, so made a point of having 12 weeks off the next year. I share my calendar with my family so that important family commitments get scheduled into my calendar and vice-versa. I’m off to school assembly on Friday at 2.30pm to see my youngest daughter receive an award. I’ll probably end up catching up on emails and finishing a report in the evening when she’s tucked up in bed.

Work where you want

I now run a completely digital office. I use technology to assist me with my clients around Australia. Last year I was in a supermarket in Santa Monica and a bank of one of my clients called. I’m sure the person on the other end of the call had no idea where I was. That evening I was working and talking to my clients back in Australia as if I was still in my office in Melbourne. I have a soft rule that every Friday I work from home and the only giveaway to my client would be the background on a Zoom call.

Bring your passion to life

When you work for someone else you may have passion for what you do, but ultimately you are bringing their passion to life. Being your own boss lets you bring your own passion to life. I follow what Trav Bell, the Bucket List Guy, is up to – he’s always doing really interesting things. He has a mantra: “People live until they’re 80 but die at 40”. His passion for living his life today and wanting others to as well is truly evident in his work.

Agile and responsive

Being in control of decisions and able to respond and change quickly is a big advantage of being your own boss. No more bureaucracy or sending up the chain of command to get approved.



One of the biggest traps I see with people that go out on their own to be their own boss is they are great practitioners but spend all their time working in their business and not on their business. How many tradies go out on their own once they have the skills and experience, only to end up back working as an employee? It’s not because they are unskilled at what they do, it’s because of all the other things they are now required to do to run the business.


Being your own boss can be lonely and isolating. I found this particularly so when I started out and was based from a home office. I then moved to an office in the city, and this resulted in me seeing more people and creating more opportunities. Recently I moved again to a global co-working office, sharing a building with 150 other businesses ranging from solopreneurs to global companies.

I have also found that those closest to you may not understand what being your own boss really entails. This is not deliberate by them, but their investment and passion are quite different to yours. As a result, your normal support mechanism may not be there. Consequently, have also started to develop a network of people that are going through a similar experience, that you can bounce ideas and thoughts with, and who become your support.

No regular salary

Particularly for practitioners or service-type business owners, having no regular salary is a big concern. It’s also the biggest hurdle for people wanting to leave employment and be their own boss. I’m happy to admit this has been a concern for me, however for me the concern is not driven by me – I’m now used to backing myself. The concern comes from my wife who is anxious and struggles to make forward plans for the family (such as holidays or updating the car). That concern is then directly squarely back at me. It’s bad enough when you worry but exponentially more so when others worry is added to your own.

No time off

Twenty-seven years ago, when consulting suites were a new thing at private hospitals, I decided to convert a waiting area at a hospital into a café, which operates to this day. I designed, funded, started and operated the café, then sold it – all in the space of a year. For anyone thinking of starting a café, be aware – it’s hard work and long hours. The most tiring aspect was that I never got a break – I’d be looking at stock, prices, layout and service wherever I went. Well-meaning friends would ask about the café and volunteer their sage advice. Even now, I receive work emails during the weekend and evenings, sometimes phone calls too. The actual email or call may be short but for a period of time afterwards, your mind is back at work.

You’re not the boss – your customers and clients are

Over and over, since I began consulting on business management with clients, I ended up stuck with finishing a presentation or completing a task due the next day – late at night and tired.

I was never able to go the normal worker’s route, in which you either get it done or have a reason for not having done it. The reality is, I needed the business and I needed the money, so I wasn’t in charge. My clients were in charge.

In a business, the health of the business is your boss and that is dictated by keeping customers happy and being responsive.

In Part One of my book Run Your Business Better, I challenge the reader to think about why they are in business, whether they are creating a job or a business, and if they want to be a business owner rather than a practitioner. For me, while the cons sound pretty awful, the pros far outweigh them, and I cannot see myself ever working for someone else. I think a lot comes down to attitude. Recognise the cons but use the pros as your oxygen and enjoy all the good things that being your own boss can bring to your life.

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