Crunch client stories: Freelance Interim Chief Technology Officer (CTO) Toby Osbourn

Toby Osbourn went self-employed in order to take control of his own financial security. Backed by a strong support network, the gamble has paid off for Toby and his business, Tosbourn Ltd.

Tell us about your business!

Tosbourn Ltd do a mixture of software development and development management. Which basically means we either help people by building them software, or help their teams to build software.

What prompted you to go self-employed?

It was always a long-term goal of mine to be self-employed, but it was spurred on by a few bad experiences in the last places I worked, where my financial security was not in my control. Going self-employed meant I was in control of my own financial security.

What were the biggest challenges you had to overcome when starting out?

Learning how much time to dedicate to working on your business, instead of in your business, was a big challenge at the start. For example, how much time to dedicate to promotion or brand building versus doing paid client work. It is something we still struggle with, not spending enough time working on the company.

What do you like most about working for yourself? And what do you dislike?

I love the flexibility of being able to work when it suits. If I’m awake early and want to get started, I can, if I slept really poorly and need a few more hours, not a problem. I also really like that my effort is only helping my family and I, and not just lining someone else’s pockets.

What I dislike is chasing invoices. We’re a small enough company that it doesn’t make sense to have someone dedicated to this task.  It is awkward having to point out when someone hasn’t paid (even with Crunch’s excellent late payment reminder!) and it adds an extra layer of stress to the work that shouldn’t need to be there.

How has Crunch helped you during your self-employed journey so far?

Crunch have taken a lot of the leg work away from us. Their easy-to-use online accounting software and expert accountants make it really simple when it comes to VAT and expenses. I am always so surprised when I hear about other contractors talking about the pains they have to go to around tax time, I barely realise the change, just a few more buttons to press and things to look over!

What’s your biggest success story from your time being self-employed?

In our three years of being a company, we haven’t once had to ask for more work off someone. Clients have either come back for more, or we’ve been recommended new work by people we had worked with before. This isn’t one big success story, but lots of little successes, making sure we’re always open with clients and always delivering on what we say.

What would be your top tip to anyone thinking about going self-employed?

Get a support network of people in similar positions to you as soon as possible, that might just be making sure you follow and chat to other freelancers on Twitter, or it might be attending meetups. It can be easy to think you’re experiencing brand new issues that no one has had to solve before, but that is hardly ever the case.

There will be good and bad projects, try not to forget the good ones when going through a bad one, and don’t be tricked that bad ones don’t exist when you’re in a good one!

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Tom West
Community and Social Manager
Updated on
April 9, 2021

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