How I turned footballing failure into business success

Over the past 10 years or so, I’ve built a career in business using my writing skills. But if life had gone to plan, I could well have been making my name using my ball skills instead.

Because between 2005 and 2008, I was actually a professional footballer. Not a very successful one mind you, but a footballer nonetheless.

So how did I go from being a footballer to running my own copywriting business? And how can you learn from my lessons and overcome your own mistakes and failures?

My first experience of failure

Derek Howie playing for Rangers

As a kid, I think it’s fair to say I was one of the better footballers in Scotland at my age.

I captained Rangers, one of the biggest clubs in the country. I trained and played with a whole host of other teams, including Livingston, Dundee United, Kilmarnock and Hearts in Scotland and Blackburn Rovers and Everton in England.

I was a good player. Not great. But certainly good. Then I turned 15.

Off the pitch, I had all but given up on school. Even though I was a clever kid, I was fully committed to leaving without any qualifications and joining Rangers on a professional contract.

But on the pitch, my attitude had deteriorated too. I was spending more time hanging around the streets than I was on a football pitch.

I was drinking. Fighting with local gangs. Getting into trouble with the police.

Then, out of nowhere, I was released from Rangers, the club I had supported all my life.

Well, at the time, it felt like out of nowhere. But looking back, I should’ve seen it coming all along. And I had no one to blame but myself.

Less than a month later, my best friend and teammate was killed in a car crash. I felt as if my life was over. His was. We were only 16.

A second chance

After I was released from Rangers, I spent a few months wandering aimlessly and wondering what to do with my life.

Despite my parents’ and teachers’ best efforts, I had no interest in continuing my education. I had my heart set on being a professional footballer. And if it wasn’t with Rangers, it would be with someone else.

So I joined Dunfermline Athletic. It could – and should – have been my second chance in football. But it didn’t quite work out like that.

Don’t get me wrong, I spent three thoroughly enjoyable years at Dunfermline. Trained with the first team regularly and made numerous reserve appearances. Signed a professional contract. Even made a couple of friendly and testimonial appearances for the first team.

But the majority of those three years were plagued by Osgood-Schlatter disease and tendonitis. And in 2008, the then manager, Jim McIntyre, who was also one of my best mates at the club, put me out of my misery and released me.

I didn’t know it then. But it was the best thing anyone ever done for me.

A second second chance

That was almost 10 years ago. Since then, my life couldn’t have gone any better.

I studied journalism at college for two years, followed by another two years at university, where I left with an honours degree.

I then joined fatBuzz, a small digital marketing agency, for two years, followed by a year at the NHS and two years working for AXA, one of the largest financial organisations in the world.

Then in 2016, I set up my own copywriting and content writing company, Howie Writes.

I’m happier than ever and making more than I ever dreamed of. So how did I turn footballing failure into business success?

Never stop learning

Derek Howie first day at school

In my final year at Dunfermline, while suffering from yet more injury problems, I realised deep down that my short-lived football career was coming to an end before it had even started.

So I decided to go to college one day a week to get a qualification in communications and literature. While I was falling out of love with football, I was falling in love with writing all over again.

That qualification helped me gain entry into college and allowed me to study journalism for the next four years. And I’ve never stopped learning since.

I go to conferences whenever and wherever possible. I read blogs and books constantly. I learn from my peers. From my competitors. From my own mistakes.

No matter what you do or where you want to go in life, never stop learning.

Believe in yourself

Ever since I was a kid, I’ve been super-confident. In fact, the only time I ever lost confidence was when I trained with the first team at Dunfermline. I was so scared of making mistakes that, inevitably, all I did was make mistakes.

I’ve never made that mistake since. Yes, I have self doubts. Sometimes I wonder whether I’m really as good as I think I am – or as good as my clients say I am.

But as my mother used to say, if you don’t believe in yourself, no one else will. And do you know what? If you don’t believe in yourself, that’s OK – just make everyone else think you do.

Know when it’s time to move on

I knew when I was released from Dunfermline that my football career was over. Jim McIntyre was more than happy to recommend me to other clubs – but I wasn’t interested. I knew it was time to move on with my life.

And ever since then, I’ve always known when it’s time to go. I left fatBuzz after two years. The NHS after one. AXA after another two.

I didn’t move because I had problems or issues. Far from it. I moved to progress my career. To gain more experience. To learn.

Now I’ve got to where I want to be, I know it’s time to do the opposite. To stay exactly where I am.

Be a people person

Guests at Derek Howie's wedding

I like to think I’m a friendly guy. And I think most people would agree. But what’s that got to do with business? In my eyes – everything.

I remember how good it made me feel when a senior figure at a football club knew my name. And I know how bad it made me feel when they didn’t. So I treat everyone how I’d like to be treated myself.

Whether you’re speaking to a cleaner in your office or the managing director of your company, make sure you treat them with respect.

Acknowledge them. Say good morning, every morning. Even when you’re not having a good morning. Ask them how their weekend was. And if they ask you, make sure you ask them back.

You might not be the best in your industry. But to get somewhere in life, you don’t need to be the best. You just need to have the best connections.

Challenge everything – and everyone

As a kid, I always asked questions. Still do. Despite someone’s age, experience or seniority, I never stop asking questions.

When I was younger, this could come across as rude and I’d get myself into arguments with coaches and bosses. But I’d like to think I’ve refined this over the years and now ask questions of the right people in the right way.

As a copywriter, you need to be prepared to challenge. And to be challenged back. But the same is true for anyone.

Don’t settle for the status quo. Don’t accept something because it’s always been done that way.  Challenge everyone. Even yourself.

Take chances

When I was 16, I left the comfort of my family home to move to Dunfermline on my own. Since then, I’ve taken every chance that’s come my way.

I’ve left roles that I was comfortable in. I’ve spoken at conferences that I wasn’t comfortable at. But despite the lack of security or experience, I grasped every opportunity.

Not everyone can – or wants to – take chances. I get that. But in my experience, you’ve got to take risks to be successful. All the best entrepreneurs do. And if it works for them, it can work for you too.

Be adaptable

When I was younger, I got called Del. And my friends would joke that when I spoke to them I was Del, and when I spoke to girls I was Derek (long before I met my wife – obviously).

In a way, they were right. I adapt to situations. To succeed in business, you’ve got to gauge the situation and speak to people on their terms.

I was brought up in the east end of Glasgow but I certainly don’t speak like I did as a 15-year-old. That’s because I know how and when to adapt.

If you’re speaking to a client that likes football, talk to them about football. If you’re speaking to a boss that swears every second word, then loosen up a little and drop the f-bomb.

That’s not being false. That’s being adaptable. That’s being smart.

Dictate your own future 

Derek as a baby

Over the years, people have accused me of being over-ambitious. To settle. To stay where I am. Sometimes I worry if they’re right. If I’ll ever be happy. Ever be content.

But now that I work for myself, I know they’re wrong. Because I’m happier and more content than ever.

My problem was that I let others dictate my future. They decided if I made it as a footballer. If I got promoted. If I got made redundant.

Why should I let others dictate my future? Why should you? The future is yours. Own it.

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