Oak Tree Practice Solutions founder, Jessica Tyler

Kultivate Winners' Series: Jessica Tyler's 'breakthrough moment'


If there was a perfect example of an entrepreneur who’s so far defied the odds and debunked a few myths it would probably be Jessica Tyler. Tyler ditched a job she was unhappy in and did what she always wanted to do – what many others want to, but never do – start a business. And guess what? One year after launching her software consulting service, Oak Tree Practice Solutions, she’s not living on baked beans while desperately chasing clients. In fact, the only part of Tyler’s story which could be described as fairly ‘typical’ is that it took her far too long to rally her self-confidence and get onto it.

A self-confessed tech nerd, Tyler’s Oak Tree Practice Solutions specialises in financial planning software offering a wealth of advice to other, not so tech savvy businesses, that are trying to make sense of it all. And there’s certainly enough of them.

Tyler talks to ShortPress about her plunge into a high-demand sector:

Describe the ‘moment of inspiration’ that led you to start your business?

“I had a breakthrough moment when sitting by a beautiful lake in Finland talking to a friend about how unhappy I was at work and felt like I was trapped in this job that I didn’t want to be in. He said to me ‘If you decide that you are unhappy, you will be unhappy. If you want to change your life, just do it.’

“That was the conversation that ignited my motivation to start planning my business, which was something that I have always wanted to do. It took about a year from there to build up the courage to quit full time work and go out on my own.”

What's the toughest challenge you've experienced?

“The biggest challenge for me is the voice in my head that tells me that I can’t do this. That I am not good enough, not experienced enough, not serious enough. The crushing self-doubt, negative dialogue and fear is my biggest challenge. I think this is something that we all face and will continue to face when owning a business.

“I don’t have any brilliant gems of advice on how to overcome it, just push on every day and get on with it and don’t let the small setbacks convince you that you’re a failure. And if something goes wrong, fix it, then register it as a lesson learned for next time.

Do you have any myths to dispel about entrepreneurialism?

“When I started by business I wasn’t expecting to be making a profit for a year. That’s what everyone told me. Within the first week of starting, I had my first client who was giving me enough work to be working full-time. And working from a home office meant that my overheads were very low. So don’t expect to be living off rice and baked beans for a year.”

What's surprised you most on your journey so far?

“The biggest surprise for me so far is that I haven’t had to chase work, it has come to me. I know I’ve been really lucky, and I can only really credit that to a strong network and choosing to specialise in something that’s in high demand. Although, I’m not complacent and know this will not always be the case. I have backups and plans for when the work stops and I need to start seeking it.”

If you had to start over, what would you do differently?

“I would have done it sooner! Seriously, I don’t know why I waited so long to do it. Just take the plunge and start, there is never going to be a ‘perfect time’ to start a business. There will always be mortgage payments and bills and people telling you that you can’t do it, you will always find an excuse if you are looking for one.

“If you can’t stop thinking about it and have planned it out then start while you still have the motivation and desire.”

What motivates you – daily?

“The drive for success is one of my biggest motivators. When you work for yourself you can’t become complacent. You need to be seeking work and improvements every day and performing your best, otherwise the work will dry up. Some days I don’t want to get out of bed, but I know I have to keep going so I can complete my work and seek more work.”

How do you feel when you think of the future?

“I’m highly ambitious. Every day I’m thinking of ways to branch out and expand my offering. I’m really excited by what can happen with work and how big it could possibly be. I keep striving for improvements in myself as well as my business, which is something that will never change. I don’t think my business will ever be ‘complete’ as I will be constantly trying on ideas to make things bigger and better.”