Escaping the 9 to 5 with Thomas Smallwood

redesign your life with Thomas Smallwood

This month’s interview is with Thomas Smallwood, one of a number of upcoming interviewees I ‘picked up’ recently over in the adventurous Yes Tribe (along with George from a few weeks ago as well). Although he didn’t necessarily follow the typical corporate career path after school, the symptoms are familiar: excessive stress, feeling unhappy, and losing the love for what he was doing. In 2016, he quit and gave himself a year to re-design his life.

Although an ongoing process, the re-design has been taking form and, as he describes on his website, Tom is now “Entrepreneur, Blogger, Mountain Enthusiast and Bibliophile”. In the interview, we talk about the messiness of the process, first in deciding to make a change and then in planning and implementing that change. What it boils down to, though, is simple: “If you’re not happy, have a think about what would make you happy!”

Watch the video for the full interview or read on to discover more about Tom’s experience below.

Redesign your life

Thomas SmallwoodThomas Smallwood started his career working in a bookstore before setting up an online business with his dad, selling used books online. When the business failed, he started stacking supermarket shelves at night to pay the mortgage, worked in a call centre, and then co-founded and sold another company. In 2016, he decided to quit what he calls the rat race and re-design his life in a way that gives him more freedom and flexibility, more time in the outdoors, and a rediscovery of what really makes him happy.

1) At what moment did you decide it was time for a change?

I think I was suffering from burnout but it crept up, gradually – it wasn’t anything that happened overnight. I actually left one job and went into another thinking that, “Okay, I wasn’t happy in that other one, I’ll go into another job and that’s going to resolve everything!” It was far from the case. I needed to rediscover my love of work and my love of life in a sense.

I felt that I needed to ‘reset’ myself and refocus on the things I love doing. In my private life, that has meant rediscovering the outdoors; in my professional life, it has meant being a little bit more entrepreneurial. That all sounds well organised but it was a messy year and a half in which I worked this out. There was no one moment, except when I phoned up and resigned and said, “Okay, that’s enough.”

I didn’t work for a couple of months – but I can’t not do anything! So I set up my website, The Armchair Mountaineer, as a way to keep myself busy and do stuff that interests me. I sat down and asked myself: what were the things that I enjoyed when I was 18 and penniless? And I used to go into the mountains with my friends. Of course, no one was reading the blog when I first set it up but it was something for me to do and think about. It ended up as a blog that’s now documenting my journey.

2) What was the biggest challenge you faced in making the change?

Fear, unquestionably. I’ve always suffered from a lack of self-confidence – I’m hardly unique in that, I think. I was fairly good at masking it at work, within that framework of the corporate life. But when you go out and do things on your own, there’s absolutely nowhere to hide. So, the biggest challenge has been dealing with the fear of wanting to make a change, of wanting to, in effect, redesign my life.

At every step of the way, the decisions that I make are entirely down to me. Although now, professionally speaking, I’m also working with other people and I enjoy that. But you know you can’t necessarily turn to someone else and ask, “Hey, what’s the best thing we should do now?” You just have to dive in!

3) Where did you get the support you needed to make it happen?

Thomas with his daughter and an elephant
Thomas’ wife has been a huge support through his transition, which has also meant that he now has more time to spend with her and with their daughter

My family – my wife, and I would say my daughter but she doesn’t really have a clue what’s going on, as she’s six years old! It’s a massive decision to step away from the ‘normal’ world of work and, although we were very fortunate that we had some financial security, it was good to have the most important person in my life there supporting me along the way.

Outside of that, it has been tricky. It might be because I don’t live in London, as I feel like it’s easier there to get into some kind of support community and to meet like-minded people. I do have a couple of supportive friends, one of whom is pretty entrepreneurial. He’s been a great support – when I’ve been having a bad day, quite often we’ll just have a chat for half an hour and it makes me feel better about things.

It’s really important to surround yourself with positive people, people who encourage you in what you’re doing. Co-working spaces can be good, just to meet human beings when you’re otherwise largely working from home. It’s good to get out there and meet people.

Facebook groups and communities can be good too. The Yes Tribe, for example, and there’s another one I would like to mention, Coffee with Dan, which is more geared towards entrepreneurs and not to everyone’s taste.

4) What’s the best part of your lifestyle today?

It’s been pretty much exactly a year now, and I feel like I’m learning more than ever before. There are loads of ups and downs, and it really is an ongoing process. There’s an excitement that comes with the potential of the projects I’m working on, and this has enabled me to rediscover my passion for working while having the flexibility in my private life. I can get up at 6.30 am, do an hour of journaling, planning, writing, brainstorming, whatever; then I can get my daughter ready and do the school run; and I’m back before 9 am to have a coffee with my wife before I sit down to work again. It’s just such a nice way to start the day, every day, instead of being crammed onto a train!

Kayak in the woods
Having a paddle! One of the perks of Thomas’ re-design…

On a bigger scale, I also get to travel a bit more with my family, around the school holidays. I can take my work with me, and fortunately my wife can as well – so it’s really about the flexibility. I also get to spend more time in the outdoors, even if it’s just going down to my local river five minutes from my house and having a paddle. How simple is that?

5) What one piece of advice would you give to someone who is considering making a big career or lifestyle change?

I gave myself a year – this year, 2017 – to change the way I live and work. I think giving myself this time was one of the best things I could have done, and I would encourage anyone who wants to make a change to have both patience and resilience. At the same time, it can’t be open-ended. I think you need to put a little pressure on yourself – otherwise, you risk doing nothing. Of course, there are financial pressures as well, which mean you can’t always just walk away. It’s a process, first, to get to the moment of committing to the change, and then it’s a process to implement it.

Once you’ve made the decision in your mind that you want to change things, look for ways of doing it and begin to implement it Get involved in the process – maybe through adding certain elements into your routine, sharing it with other people so that it becomes public, or joining communities of like-minded people. You need to do something that builds up positive pressure on you to actually go through with the change. Like in all journeys –  physical, mental, or metaphorical – the first step is the hardest and once you start you are much more likely to finish! But it’s not going to happen overnight.

Also, one exercise that I do fairly regularly is to just take stock of what I’ve done over the last few months. It can be really banal things, like that I’ve learned something about email automation, to take a random example. When you start to make these kinds of lists, then you realise how much you can learn and progress over time.

You can find Tom’s blog and learn how he’s ‘finding a way to live better’ over at You can also find out more about his latest startup, which helps entrepreneurs and small businesses to grow with Virtual Personal Assistants.


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