What to expect from your first year self-employed

Patrick McMaster, executive coach and owner of Aim High Achieve More, shares his experience of becoming his own boss

Self Employed


Twelve weeks after starting my own business, my wife said to me “If this is what it’s going to be like….I’m not interested!”

In the preceding week I’d overly harshly criticised my 14-year-old daughter for social media use on her phone and started a three day disagreement with my wife over which sport another daughter should play at the weekend as two teams in two different sports wanted her to play for them.

At the time that my wife told me I was being unreasonable, I didn’t recognise this was part of the journey. As I mark one year self-employed, this is a short summary of key moments that many self-employed people may recognise…


Aug/Sept 2018 – Having worked in corporate environments for circa 20 years my confidence was knocked when I was made redundant. Working in HR, I’d helped make plenty of people redundant myself over the years. A little sad and bitter I decided that I’d never get as good a job as the part time one I held at England Rugby and set out to create my own new working experience. I learnt how to run my own accounts using Xero software and about indemnity insurance, corporate tax etc. A good friend recommended “Be More Pirate” – a book that on the face of it aims to take lessons from pirating history and apply them to modern settings – which is excellent for start-ups in my opinion.

I asked my three kids and wife which of the (I thought) clever company names I’d considered for the limited company name and website they preferred. My 11-year-old daughter didn’t like my ideas and suggested “Aim High Achieve More” summed up what the business was about. My other two daughters helped me file and label 20 years worth of my materials and resources.

Oct/Nov 2018Adelante Design, run by family friend, Richard, designed my corporate identity/logo and delivered what I believe to be a first rate website. Terrified and excited, I made my first post on LinkedIn (to my connections only) to announce I was open for business. I have strong opinions about social media and blogging and it feels authentic to me to blog quarterly. I’m not a fan of daily posts on LinkedIn with people standing in front of corporate logos/receptions showing where they are that day. Through my network I started working with Leading Edge on a collaboration with Team GB. My dream client perhaps?

Dec 2018 – A friend of the family engaged me to do some consultancy for his business. Was he making a charitable donation or genuinely seeking support? Imposter Syndrome is a frequent visitor in the first 6 months.

New year

Jan 2019 – I went back to my previous employer to do a days work. It felt familiar and easy….not like running your own business at times.

Feb 2019 – Paid work started to really accelerate in a positive direction. My strategy of focusing on working for 3 consultancies all with different offers to the market, as an associate, started to pay off. I was getting busy and starting to cover my cost of living and running the business.

Mar 2019 – I upset one of the three consultancies I work for by having a conflict of interest with a potential client of theirs. I was asked if I would work exclusively for them in one particular area and I had to politely decline. Difficult conversations have to happen when you’re self-employed too.

April 2019 – As a family we managed to have a 10 day holiday in Turkey AND I managed to cover my costs still.

May 2019 – I find myself in Chicago and Miami in the same week doing work for different clients and in Milan the week after. Is this the new normal?

June 2019 – Working with customers for the second or third time – different types of pressure and enjoyment – have I told them story X before?! I hit break-even before the month had started.

July 2019 – I look back on year one. My brother also started his own business in the same month. It’s ironic and exciting to share the journey with him.

August 2019 – My most important role is that of being the best dad, husband person I can be.

Other reflections

I know now that I will never work for one sole organisation again. I love the variety and challenge of different clients and different sectors. I really love the fact that some weeks I can attend different sports or school events with my children. I love that I can be there some days when they come home from school and hear (albeit briefly) about their day. I love that even though we have holidays I feel rested and invigorated everyday anyway – holidays are a bonus.

In the first quarter I invoiced just £500 which definitely contributed to me being a bad parent and husband at times….however in year 1 overall I have managed to generate a small profit and even a pension payment – something that I’m told is quite rare for start-ups and I’m proud of myself.

As I look to Year Two, I feel grateful to have six months of work booked in already and I’ve achieved my targets for the next three months already. I have work trips booked for New York, Denver and Hong Kong in my diary.

Ultimate goal

However, if I find myself regularly working above/beyond capacity and missing out on home experiences I will have failed to achieve my ultimate goal.Thank you to my wonderful wife Rachael and my kids, Lucy, Emily and Sophie who’ve supported me in the tough times and have celebrated the wins with me over this past year.

I know that I’ll never be certain three months ahead whether or where I’ll be working and that there is no security or certainty. At the top of my ‘to do’ list I have ‘Enjoy the Journey’ written in bold letters. I’m confident that Year Two will be even better than Year One!

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