March 2007 is when I registered with HMRC as self-employed. I was 19 years old. I setup my first website and the journey began! Recently I’d been thinking back over what’s happened during the last 10 years. Here I will share my thoughts and hopefully you can learn some big lessons from them.

There are lots of great stories online of people sharing their successes. You often don’t see the other flip side of the coin and I hope it can be just as valuable to read about struggles too.

Self-employment is a journey, a flipping bumpy journey!

It's not about destination, it's about journey quoteI know saying this sort of thing is a bit of a cliche that you will see repeated in other areas of life. But it’s the truth. “It’s not about the destination, it’s about the journey.” I think it’s very true with going it alone. Whatever stage you are at in your entrepreneurial journey I hope you are enjoying it, I am, most of the time.

My decade long journey hasn’t only included owning websites. I was a short-term stock market trader for 2 years. I also spent just over a full year developing smartphone apps. I’ve also made small investments in new companies and tried things like eco-friendly debentures.

One thing I’ve came to appreciate over time is that the unexpected will happen. When and how you aren’t allowed to know! Your journey will be a bumpy one. When I say bumpy I mean some nice bumps upwards and some bad bumps back to earth!

With that been said let’s look at why mine’s been bumpy and what can you learn from it.

A lovely bit of unexpected help

Better to be proactive than luckyWhen I left school I worked part-time in a supermarket. I stayed at the supermarket for a couple of years after registering self-employed. This is when the first unexpected event happened. I had an email from a company. They were a company I had been promoting through affiliate links. They offered to increase the commission I received and help me optimise my website. It made a huge difference and it allowed me to leave my part-time job in the supermarket! Since then I’ve earnt $54,000 from them.

Lesson 1: other people’s help, especially at the start, is vital. It showed me very clearly that other people were a hell of a lot better than me at this website ownership malarkey! I got lucky in that they emailed me but being proactive is better than relying on luck.

Why would you not adapt?

Early adopter of new technologyAfter bumbling along for a few years things started to really change in the online landscape. You have to remember that social media was still very new when I started. In 2007 it wasn’t the done thing to have a Facebook page, twitter account and pinterest account for your company. Heck, Pinterest launched in 2010, I’d been self-employed for 3 years by that point!

Things were really changing with search engine optimisation as well. I didn’t adapt quickly enough to those things. I was used to web directories being my best weapon for promotion! It lead to me not growing and my websites slowly declining.

Lesson 2: You have to adapt. Why would you not? You would think it’s obvious. But sometimes you can’t see the wood for the trees. Stay in the loop and try your hardest to be a quick adopter of new trends no matter what industry you operate in.

Don’t get ahead of yourself

Wait for cash in bank quoteMy first experience of potentially coming into a decent sum of money was a very harsh lesson. I can’t remember exactly when it was, maybe in 2010, I purchased 2 domain names. They were single-word domains. I paid £3,000 for both. With the market for domain values expected to grow nicely I was very pleased with my purchases.

I sat on them for a couple of years with basic websites on them so they got a trickle of traffic. I then decided to sell using a website called Sedo. The domains were classed as “premium” names and a domain broker called me. He wanted to achieve £10,000 for each domain. He was planning to start negotiations a lot higher though. I was unbelievably happy!

It didn’t go well. After months of phone calls and talks with all sorts of potential buyers there was no sale for either domain! I was absolutely gutted. In the end we just stuck them in an auction and they both sold for £2,700. That’s right, I made a £300 loss.

Lesson 3: Try to keep level-headed and focussed as much as you can. Until the cash is locked in the bank you can’t be sure of anything.

Look after your health!

Hunched over PC screenAs I mentioned earlier – I was 19 when I first became self-employed. You would think me mentioning health is ridiculous! It’s not. 3 years ago I had a serious problem with one of my eyes. My eyes were not the underlying problem. I was diagnosed with a type of arthritis. A fairly gutting thing at the age of 26. After my initial problem with my eye I had 23 visits to the hospital in just over a year before I was discharged.

This happened at the time I was doing short-term stock market trading. I didn’t do any work at all for 2 months. I went back to full-time after around 3 months. I’d lost all my confidence. It felt like I’d never worked before. I felt completely lost. That is a disaster in any occupation but even more so when it comes to trading. The profit I’d made the 6 months before my eye problem disappeared. To cut a long story short; I ended up going 12 months without earning anything.

The whole episode happened out of absolutely nowhere! I was fine and then boom, my eye went horrible and the rest is history. After that episode I stopped trading and now have a nice cataract on my eye the NHS can’t afford to remove. I never ever expected those events to unfold.

Lesson 4: Even if you are healthy now you need to make an effort to maintain your health. Sitting hunched over a PC screen all day is really bad. Make sure you take action to counter-act the negative effects of it. I now make a big effort with my health and you should too throughout your entrepreneurial journey.

Try not to run out of money!

External forcesAfter my health problems I decided full-time trading was not for me. I’d considered moving away from it anyway because I lacked deep pleasure from it. Eventually I moved into app development. I love smartphone apps so it was logical. I enjoyed it a lot.

Unfortunately it didn’t go how I wanted it to. This would end up being a long story if I went through it all so I’ll keep it short. I planned to launch the apps after an extension had been finished on my house. It was a nightmare, it took 5months longer than expected. It was a major extension on the house which meant I had to move out for 3 weeks (which was always the plan). After coming back I would launch the apps. I’d well and truly ran out of money by then!

Lesson 5: external forces will always have an impact on your work. I was stupid for not having a contingency plan in the event of the building work hitting major issues. The problems weren’t my fault, leaving myself vulnerable was my fault. Always look ahead to what’s going to be happening in your life and prepare accordingly.

Your personal life will affect your self-employment

Love is more important than moneyLast year contained yet another huge challenge I didn’t see coming! When on a friends stag do I met an amazing girl. The big problem was we lived a long way apart, nearly 2 hours. We tried things anyway and to be fair it worked for a while, it was awesome. I won’t go into details but it ended after 9 months together. It ended very amicably, there were just too many pressures. One of those pressures was work for both of us. All the travel and spending weekends away had quite a negative impact on my work and it does create problems unfortunately.

Once again I never saw that whole 9 month period of my life coming. I just went on a night out and it completely changed my path for a while. No regrets at all though. Love is more important than money.

Lesson 6: whether it’s relationships, babies, family deaths or even pets dieing – your personal life will affect your self-employment. Sometimes it will severly affect it. The only other choice is to have no friends or relationships :p No thank you!

Lots of little bits of advice

Forgive yourselfI could have put other things earlier in this article but I wanted to pick out the biggest things that have happened to me and what can be learnt from them. Here are some other bits of advice, they are arguably just as important:

  • Give yourself time. Most things will take longer than you expect!
  • It’s not easy. Some bloggers love to write articles about how setting up websites and making lots of money from it is as simple as following a few steps. It’s not. Whatever your venture I am 99% sure it will not be easy, you’ll have to learn alot.
  • Forgive yourself when you mess up. We all do it. Don’t forgive yourself if you keep making the same mistakes though! Kick your ass into gear in that case.
  • Take criticism on the chin. It’s inevitable. Learn when you can from it. If it’s stupid critiscm then laugh about it!
  • Be proud of yourself. Some people don’t even have the guts to try!
  • Do things your own way. Learning is important but ultimately it is taking action and finding your own way that’s needed.

That’s pretty much everything I can think of right now. It’s turned into a pretty big article! Thanks for reading so far down.


Will me sharing these actually help you? It’s up to you I guess! How much they will help partly depends on where you are at in your journey of being an entrepreneur. Honestly I think some of them may be the sort of thing you need to experience for them to fully sink in and help you going forward. Others you can, and should, make a conscious effort with.

Life has ups and downs for all of us. Trying to go it alone compared to having a nice solid 9-5 job can create even more ups and downs. Just please always remind yourself that work is not the most important thing in life. Your relationships and your health are the most important. Remind yourself of that and it will stand you in good stead when it comes to the ultimate daily aim, happiness.

Are you willing to climb the mountain of happiness? I sure am!
Personal goal meme