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Solopreneurs – and the 1 massive problem of knowing when to let go

It’s not all good times running your own business as I know all too well

life as a solopreneur

To the manor born

The word or phrase solopreneur irritates me.

These days we seem to have a desire to hang a title on everything and the notion of working for yourself has not escaped the naming phenomenon. 2023 seems to have seen the birth of solopreneur experts. You can find them writing books, creating YouTube channels and even TV shows about them.

The truth is there is nothing new about being a solopreneur at all, despite all the hoopla and current hype & commotion. It’s just in the good old days it was called working for yourself, being your own boss, or plain and simply being self-employed.

For me, I guess the writing was on the wall that I would always follow my own path as I was born into a family where my dad was self-employed – or a later-day solopreneur if you will! It’s all I knew.

Long summers

I used to spend all my summer holidays with my dad at the factory – geez, looking back he must have had the patience of a saint! Summer holidays, Christmas holidays, weekends – anytime I could I would be with him I would jump at the chance.

Obviously, there was a wee bit of hero worship going on there and I’m not ashamed to admit it, but also, he was subtly teaching me the trade (which happened to be printing & design), but more importantly, he was teaching me how to run a business, deal with suppliers, interact with customers and balance the books.

Much of running your own business or being a solopreneur is pretty unrewarding and unglamorous. Long and odd hours are a given and you need motivation by the bucket load. By definition, you have no one setting your agenda or sorting your calendar. Each day it’s up to you how much you do, when you do it and in what order you do it. I guess that for me has always been the appeal, but it has never been a conscious decision – I simply never knew anything different.

Time goes on

I left school at 16 and after briefly playing cricket professionally, it was always the family business that interested me. The company my dad had set up in ’71 was even named after my sister and myself – DAvid and RUth – he called it Daru Graphic.

Although he never tried to force my hand into joining him in the business, he was a crafty and clever sod – all those school holidays I spent with him bore fruit as the years passed by. Of course, at 16 I had a huge amount to learn, but equally, I was already on the road and wasn’t intimidated by the notion of running a business. The idea of spending a Sunday afternoon invoicing, or finishing work and then driving around delivering to customers seemed natural. The solopreneur lifestyle was shown to me early on.

Eventually, as he began wanting to spend a little more time living and not just every hour working, we became partners and I was doing more and more of the hands-on day-to-day running of the company.

It seems fitting that the last time I ever said goodbye to my dad was at that factory. I lost him way too young, but I worked with him every day from 1983 – 1998, and I learned more from him than I could have known.

Times change

I carried on running the business and it went through a crazy spell of growth.

I was still doing everything alone and I was a single dad as well. This isn’t a tale of woe though, far from it. Like I keep on saying, it was just a natural thing for me to do. I was loving every moment of it and of course, I was proud to be carrying the company forward in his honour. My mum was still alive and I felt I owed it to her to make a good go of it as well.

With things booming, I decided on taking a huge risk, one my dad probably would never have taken. He kept his margins high and overheads low which is a classic business strategy and one that served him well. Only now do I realise what a hell of an astute businessman and solopreneur he was.

But, being my own man and always having belief in my decisions (and with the balance sheet backing me up), I took the plunge and risked it all!

I moved from the factory, the only factory that Daru had ever been in and at the same time I invested in a £275,000 German-made press. The idea was that I could turn out more work, quicker and to a higher quality. I took on staff to free me from running the press so that I could run the business.


Luck wasn’t to be on my side. Just after I’d signed on the dotted line for both the press and the lease to the new factory space, the 2008 recession started to bite – and hard.

Clients were either going out of business or being way more cost-conscious than they had been just a few years earlier. I was also learning how to deal with staff which is something that I had never had to learn before. I now had what was for me at least, big overheads to meet. The press, staff and rent all needed to be paid ahead of me. That eventually took a toll at home as the mortgage had to go on to a repayment plan.

These are the stories that these Johnny come lately solopreneurs fail to tell you.

There are good times for sure, but there are no guarantees that they will last forever. And now we are getting to the nub of what I really wanted to get over today – learning when to let go.

A fool’s pride

We are all clever in retrospect, right?

At the time I could not have been more dogged and determined to make things work. I kept on thinking one more order would turn things around. There would be one client or contract that would change things back to how they once had been.

By that time though the company, and myself, were in constant overdraft, and I had plundered any savings I had into the company and I wasn’t even paying myself. I took out personal guarantees to be able still to trade and get credit.

Stupid as it sounds, I didn’t want to be a failure in my mum’s or daughter’s eyes (even though she was barely 10) and I hated the feeling of running the family business of thirty-odd years into the ground.

But the time did eventually come when I could no longer deny the truth that had been staring me in the face – I had to close it all down. In 2012 I went through the voluntary administration process which was tough – but here’s the thing, I should have done it five years earlier.

One major problem with being a solopreneur (much as I hate the word I sadly need SEO ranking!) is that it’s all too personal, and consuming. You don’t get the chance to step back and see the wood for the trees. I had too much pride and I simply couldn’t or wouldn’t be told.

Learn to listen

To this day though, I’d have it no other way.

Within a year, after the wounds had started to heal and the dust settle, one May evening in 2013 I decided to start a new company – why wouldn’t I? It was all I knew.

Ten years on and it’s still with me. Do I have the same feelings about this company as I did about the family one? No, but there is some pride that I used the family knowledge to start it up. I think the old man may even have been a little bit proud actually.

Through the COVID lockdowns, I could see though that the company would not come through unscathed – at least the battle scars had served me well and I had learned something from having gone through administration.

A lot of the clients I had dealt with had been hit hard and closed and the general picture of the kind of work I had been doing pre-COVID was changing for good.

So what did I do? Of course, as you’d expect, I thought of what other ventures there were for me to work for myself. So, I reinvented myself yet again.

Scratching the creative calling

In September 2021, I began to earnestly follow the dream and goal of becoming part of the content-creator economy.

Part of the way I got through lockdown was to watch a lot of YouTube – tutorials mainly to stop my brain from turning to mush! But in consuming so much YouTube I started to learn there was money to be made from making videos. Then I learned there was money to be made from writing too.

It all appealed to me and those solopreneur fires were once again burning deep within. I could feel the buzz and excitement all over again.

Setting up this business was very different though. The company I’d set up in 2013 was very much in the embers of Daru. I used the legacy of the customer base that my dad & I had built up and ‘simply’ morphed it into a new company.

But this time around everything was new to me. I had no contacts, no one to ask ‘how to’ and no knowledge of the business. CPM & CTR were phrases I’d never heard of before. But to me, that is part of the buzz I guess. What was the alternative? Working for someone? No…I don’t think so thank you very much.

Wrapping up

With all the perils that working for yourself brings, I’d have it no other way.

No fixed, paid holiday, no guarantee of a regular salary and the fear of not being able to pay the bills – those are all part and parcel of working for yourself.

COVID gave me the excuse and the opportunity to explore something new and not settle back into the safety net of what I knew. I have had to push myself like never before to learn new talents and skill sets, and I am loving it!

It has rejuvenated me and given me a fresh new passion for what I do each day. I’ve had to learn to be patient and let the seeds I have been busy sowing for the past twenty months grow. And you know what? There are just signs all that energy may not have been wasted.

The day and lifestyle of a content creator is me all over. Setting my own agenda, hours and working alone – all are required in this new creative life I have chosen to pursue, and it suits me perfectly.

Sure, it is not paying me enough right now to get by on, but there are no debts attached and the signs are promising. I am not trying to pay and feed others, but just getting back to basics. I doubt it will make me rich, but if it pays enough for me to get by on, that’ll be enough – and I’m happy.

I’d like to think my mum and dad would be proud of my endeavours – that still and will always matter. After all, they made me into this person, all I am doing is carrying on the legacy.

But, I am setting goals. This cannot be a vanity project and it needs to start to pay some bills, but equally, I am learning a whole new business so I need to give it time – just not too much. Once burned…

And if you were here with me now chatting about starting a new business, I’d be one hundred per cent behind you. Working for yourself is the best, most exciting and invigorating way to live your working life. Why clock in each day and make money for someone else when you can do it for yourself and your way?

But – if things do start to sour, no matter what emotional attachment you feel to what you’ve created, no matter how many hours and late nights you’ve invested into it, don’t be afraid to close the doors and walk away.

Don’t sell your soul and chase the devil. Sometimes things just don’t work out. Take what you’ve learned and move on.

An entrepreneur or solopreneur never dies – it’s just what we are.

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