Eric Wroolie on his career change
Eric Wroolie, Overpass Apps. Image: Eric Wroolie

From teaching to tech: ‘I honestly didn’t think I was smart enough for IT’

7 Mar 2018

Have you ever thought about making a dramatic career change and moving to tech from another sector?

Not everyone who works in tech starts out there. Career pivots are becoming more and more common, and a dramatic change in industry isn’t the shock it used to be.

Particularly as the technology sector rapidly expands and opportunities are growing every day, more people are making the decision to make a complete career change and move to the technology sector from a wide variety of backgrounds.

Future Human

Eric Wroolie is one such person. Currently, he runs a small app company called Overpass Apps. Over the years, Wroolie has been in a number of different sectors and worked for countless big names, including Deutsche Bank, BBC Worldwide and Macmillan Publishing.

He spoke to me about his meandering career path, which eventually led him to the tech world.

Before pursuing a career in tech, what work were you doing?

Before getting involved in technology, my goal in life was a be a history teacher. After high school, I joined the US army as a linguist. They sent me to the Defense Language Institute in Monterey, California, to learn Chinese Mandarin and later to learn Vietnamese.

When I got out of the army, I went to university to get my teaching degree. I worked in the state of Missouri as a supply teacher (or substitute teacher, as we called it) and graduated in 1998.

My wife was English and she had always wanted to move back home. I thought this would be an incredible opportunity to live in Europe for a maximum of two years, and seeing all the historical sites might help with my teaching ability. We also had a new baby on the way.

I finished my degree in May 1998 and moved to the UK immediately after. Now that I was university-educated, I figured I should be able to find a good job. But nobody wanted a certified US history teacher in England.

So, I applied for every job that was available. Despite sending about 10 CVs a day (through the post, because I could not afford internet), I only got a couple of interviews.

I mean, I applied for everything! I tried to get a job as a salesman, a security guard, and I was very close to getting a job as a night manager at a Blockbuster in Oxford. But when the manager asked my salary expectations, I told him I needed £15,000 a year and he said the job only paid £11,000. I honestly cannot understand how anyone could afford to live here.

I got a lot of rejection letters, but most of the time I got no reply.

One of the jobs I applied for was for an IT trainee position at Barclays Capital in Canary Wharf. Strangely, I was invited for an open evening interview. I had sent out so many CVs that when I got the invite, I couldn’t even remember having applied.

At the time, I was working in a yoghurt packing factory in Wantage. Every night, I wore overalls and white wellies and packed yoghurt into boxes from a conveyor belt. After two months, I feared I would be there forever. I even met another person there with a history degree. We worked from 10pm to 6am.

But I had an interview in London. I didn’t have a suit that fit me, so I went to the Save The Children charity shop in Abingdon and bought one for £8. I wore my army shoes. And I took a train ride I could not afford to Canary Wharf in London. The only technology experience I had on my CV was WordPerfect experience (and an emphasis on a clean driving record).

‘It’s a strange thing about technology. Wherever you get on, you can become the expert’

At the open evening, I made small talk with other people interviewing. Everyone was far more qualified than I was, and I was surprised I was even there. I remember talking to a project manager who flew in from Glasgow just for the event. When I told him I was working at a yoghurt packing factory the day before, he stopped talking to me. I think he was wondering whether he was wasting his time at that event, and I certainly was wondering whether I was wasting my time because there was no reason I should be there.

Back in 1998, everyone was getting in the technology space and Barclays was willing to train someone who they felt was a right fit.

I had two interviews that night, and they mostly dealt with problem-solving questions. An example question was: ‘Give me five reasons a manhole cover is round.’ After the shock of seeing the tall buildings and marble columns, I was starting to enjoy myself. It was obviously a mistake I was there.

So, I answered each question and smiled and laughed internally at the situation. I was a yoghurt packer in a second-hand suit and these guys were all technology professionals.

They hired 10 people that night. And I was one of them. They asked if I would accept an offer of £26,000 and I honestly thought they were joking with me. I started two weeks later.

My new boss (who was not one of the people who interviewed me) frequently complained that he did not know what to do with me. He was showing me a task to do on the first day that involved moving data from Excel into an Access database.

I asked what the difference was between Excel and Access and he walked away, disgusted, and sent another member of his team to talk to me. Hugely embarrassing. I asked the same question of the other person and he told me that Excel is a spreadsheet and Access is a database. I nodded as if I understood but I didn’t. My boss was another American and, despite everyone thinking we should get along, he couldn’t stand me.

‘If someone offered me a job as a history teacher now, I’d laugh in their faces’

Barclays Capital had a ‘learning library’ for the IT departments. It stocked up on all the latest computer books and you could check them out for three weeks. I had a two-hour commute each way, every day, and I spent all that time reading.

Unlike others, I was behind the curve on everything. I hated the embarrassment of not knowing what others were talking about. Soon, I had read everything they had in the library and started buying my own books.

For some people, the Bible is the book that has most changed their life. For me, it is Visual Basic 5 in 21 Days.

It’s a strange thing about technology. Wherever you get on, you can become the expert. After six months, people were coming to me with questions about Microsoft Access or ASP. After a year, I was doing very well and getting some pretty decent bonuses each year. People teased me for reading the big books but I quickly found that the things I thought they all knew, they didn’t. So many learned on the job only.

I took every course I could and got Microsoft-certified as early as I could.

After two years at Barclays, I moved to a smaller company in Reading for a few years. Then, I started contracting. Eventually, I was making more than £100,000 a year. I still value keeping up with technology – right now, it’s apps.

If someone offered me a job as a history teacher now, I’d laugh in their faces. I feel like I really dodged a bullet.

I sometimes think that if I had come up the ranks with a computer science degree, I may have thought my education was over when I left school. But, in this industry, the learning never stops.

What made you decide to change your career track?

I honestly didn’t think I was smart enough for IT. But my desperation made me go to that interview. I can remember thinking that these skills were for ‘someone else’. I’m so lucky Blockbuster didn’t hire me.

Were there any challenges that made you nervous about jumping industries?

Yes. It’s daunting because you are starting over again. So many people in tech know what this is like because our skills can become out of date in a few years.

But, coming from outside, you don’t expect that. If I was a history teacher, I’d probably be doing things in a very similar way to when I had started.

What advice would you give to someone who is thinking about switching their career?

We live in a world where people tell you that if you don’t get a good education (or a good degree), you’ll be a failure in life. I can remember high-school teachers saying that.

And I think that, in today’s world, the university education is not as valuable as it once was. When I’m hiring someone, I actually don’t care if they have a degree or not. When I’m hiring an app developer and I have to choose between someone who has a portfolio of apps on the market and someone with a university education, I’ll choose the former.

I think changing careers is so much easier today than it ever has been. But if you are of the opinion that you need to go back to university to do it, I can see how that would be a huge risk.

Jenny Darmody
By Jenny Darmody

Jenny Darmody became the deputy editor of Silicon Republic in 2020, having worked as the careers editor until June 2019. When she’s not writing about the science and tech industry, she’s writing short stories and attempting novels. She continuously buys more books than she can read in a lifetime and pretty stationery is her kryptonite. She also believes seagulls to be the root of all evil and her baking is the stuff of legends.

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