Escaping the 9 to 5 with Terri Witherden

how to start a graphic design business with Terri Witherden

In this month’s career transition interview, I’m speaking to Terri Witherden, who I met in a canoe on the Mississippi River back in 2015 and who has since worked with me in a couple of my different coaching programmes. From working in a corporate marketing role, Terri has evolved her business into providing digital design for what she calls ‘conscious businesses’.

I’ve been honoured to have been able to follow, and support, Terri’s journey since that chance meeting in 2015, when she first woke up to the possibility of taking control of your career and living your life with more intention. It’s been incredible to watch her grow and evolve into the confident business owner that she is today.

Watch the full interview and read the transcript below!

How to start a graphic design business

terri-witherden-profileTerri Witherden is a graphic designer who specialises in helping conscious businesses tell their stories through their visual identity. She is also passionate about productivity and helping people plan their time with the digital planning tools she designs. She came out of corporate life in 2016 but the journey between leaving London behind and finding herself running her own business on the West Coast of Ireland has had many twists and turns…

You can connect with Terri on Instagram, LinkedIn and on her website.

*Note: Our initial interview recording did not come out well and so we redid the video. We kept the original transcript so, as a result, it won’t match the video 100% – but both versions have incredible insights from Terri!*

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

Anna:               I’m really happy to say that this month I’m with Terri Witherden for the Fearless Fridays Career Transition interview. So Terri, why don’t you tell everybody what were you doing before and what are you doing now?

Terri:                I’m a Digital Designer, specialising in Graphic Design and Visual Branding identity for Conscious Businesses. Before I started my own business, which has been quite a higgledy piggledy journey to get to this point (and I’m sure it will be higgledy piggledy some more by the time I retire), I was working in a corporate marketing position. Fresh out of university into the big smoke, I loved it. I absolutely loved it for a few years, and then the fear, the dread, the overwhelming: “This isn’t me” started to creep in. So, I had to make a change.

Anna:               I think was it 2015 we met in the Mississippi? So we met on this little adventure trip which was all designed around helping you think about what was important to you – and for me that came faster because I had already started making those changes, but I think for you, that was quite pivotal. So, where was that decision point for you? What was the trigger?

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

Terri:                Yeah, I think it was, you’re right, we met on the Mississippi river in 2015. That was, I would say, almost pre this journey. I was so new to the idea of actually being able to take control of my own life, take control of my career and be a separate entity outside of a company. I was hanging around with yourself and lots of other inspiring people who were carving their own way. I was part horrified, part awestruck by it. So, that was the time for me that really started to get the cogs to turn.

But already from that point, I’d begun to get quite unhappy in my job. It had gone from being everything I ever wanted to feeling very oppressive – both the city environment itself and position. I’ve now moved to like really rural West Ireland, where I’m flourishing, so, city wasn’t great for my mental health.

The role had changed from things I loved, which was content producing, marketing strategy, copywriting and email flows and everything like that, to predominantly PR, which just isn’t particularly something I enjoy. I could do it and I was good at it, but I was slightly soul crushing. So, that was the point when I realised, as I began to meet people who were doing their own thing and using their own skills and (this was what was really revolutionary to me) they weren’t just using their own skills, they were combining them with doing things they loved. So, if they wanted to just travel around the UK on a paddleboard, they’d find a way to make that happen and monetize it, and I was just astounded That was the beginning.

Anna:               Yeah, definitely. It’s exciting. And it’s just [inaudible 00:03:11] to meet other people who are doing things like that. The danger for me is always is you sort of get caught up in their thing, and go, I need to go paddle boarding around the UK. That’s not necessarily the dream for me. It’s the fact that as you say, people, they occupy the things they love, things they’re good at and making that work. So, you mentioned the higgledy-piggledy daily and I’ve certainly had a higgledy-piggledy tendency too, so, what have been some of the challenges that you have experienced?

Terri:                I think the challenge is, and it’s one that I kind of feel like I’m over it and then it will come back with absolute vengeance, is self-confidence, and just the belief of, can I do this? Should I do this? Is this the best thing to do? Am I wasting time? They’re quite eroding thoughts as well. So, once you’ve had those thoughts, if you don’t get them under control, they’ll gnaw away at the foundations of everything you’re doing. So, you’ll keep showing up to find clients or calls or do the work, but you’ll kind of lost that strong foundation.

So, there’s been a lot of work through the years on firstly finding clarity in what it is I want to do. So, I shifted from predominantly word-based content production into design, Photoshop, illustrator, illustration, things like that.

And that, I don’t know if it’s something that a lot of people I’ve spoken to experience it in school, like, great, you’ve done really well at art, but what about your maths? Creative endeavours often get pushed to the bottom. So, I’m also, as well as kind of questioning, am I doing the right things in terms of my career path, I’m often questioning, can you make money being creative? And that’s a block I’ve had for a very long time and every time I think I’m over it, it will, it will manifest in, in another way, or it’s just a very deep-seated… but the only way to prove that you can do it and prove it wrong is to just go do it. So, you just have to keep producing creative things and making money from them and soon but surely, hopefully we’ll get there.

Anna:               That is interesting, because I know that’s common for anyone starting a business and working for themselves, I do think the creative field suffers even more, and I think as you said, sort of school and parents and society tell us you can’t earn money doing that. You can’t be creative.

Terri:                It’s the starving artist.

Anna:               Yeah, that’s interesting, but what are you actually going to do with your life, right? Another starving artist, exactly. So, I guess where, from whom, did you get the support? Sounds like you’ve done a lot of work on yourself. What have you done to get over some of those hurdles that you’ve come across?

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

Terri:                So, the support is surrounding yourself with like-minded people, like going to coworking spaces. I was a digital nomad for some time and would be living and coworking in some really great spaces around the world. Surrounding yourself with other people who know what you’re doing and they’re doing it themselves, surrounding yourself with role models who are making money doing what you want to do. Whether that’s in the coworking spaces or certain Facebook groups, you’re following other designers who are producing prints and stickers and pins, and you’re just like, Oh yeah, this is actually a thing, it can happen. So, that’s been a great source of support.

And then also audiobooks and podcasts, just going for an hour walk and absorbing. It doesn’t always have to be about business either. I listen to a lot of fitness podcasts and audiobooks, that there’s a real link between, I think, the resilience of getting through a half marathon and getting through a tough stint in your business. So, it’s all about that kind of mindset (this is bad now, but it won’t be forever) and just changing your mindset around how you deal with these hurdles.

I’ve also worked with yourself quite a while. I think getting a coach is, I actually remember in one of my audio books, I think it was Jen Sincero, she’s just like “hands down, it’s the best thing you can do, because you’re wondering around in the maze crying and hungry and sad and someone who’s done it well before and is a few steps ahead of you is on top of the mountain watching you struggle, eating an orange, saying, just go left”.

They can see it from a different way from you and having someone to sort of bounce ideas around with, especially as a freelancer or new solo business owner, having someone to bounce ideas around with and just get clarification is so important. Those would be my support sources.

Anna:               That’s such an interesting metaphor, I’ve never heard that. I don’t see myself standing on a mountain eating an orange, but I know what you mean. Even if you’re just a year or two ahead of somebody, you don’t want to get too far away. Because I had a coach who now is, you know, “8 – 9 figures” and she just got a little bit too far with the team of 37 people and so, and that’s no longer relatable for me.

But I was going to say, just a few steps ahead, a few years, a few thousand pounds of whatever it is, and just to really you and navigate some of those hurdles. And we’ll still make mistakes and we still need to find our way to make our decisions, but as you said, there’s no reason to struggle. And even for coaches, being the sounding board when you need someone else to have the extra outside perspective. It saves so much time and energy and not to mention being more fun when you have someone to partner with.

Terri:                Yeah, completely. There was another coach that I was working with who I did a lot of money mindset work with, and she’s this incredible, she’s weirdly actually, I think she appeals to my London lifestyle part of me that isn’t quite ready to let go of avocado on toast on expensive rooftop bars. She’s absolutely smashing it. But in the two years, since I started to work with her, she’s now gone off on a different trajectory and she’s aiming to be a millionaire within the next 18 months.

And it’s great, but suddenly all the content she’s putting out, it’s very Bentleys and Rolexes and I was going along with it. I was really like, actually, yeah, I can make all this money and I’m going to love it. And then I just checked myself and it was like, don’t get me wrong, I love a really nice pair of shoes, but I live in a really remote area, which it’s raining like 90% of the time. I don’t need Luis Vuitton, nor would they make me happy.

So, it’s about checking in with yourself and making sure that the people you are being inspired by are actually still in line with what you truly want. And it’s very easy to want Bentleys and Rolexes and helicopter rides into town just for lunch, but that deep down that isn’t really going to make me happy personally.

Anna:               That is really interesting. And I think allowing that to evolve and it’s okay… And it’s also, again, that danger of latching onto someone else’s definition of success. So, I think as much as again, it’s helpful to work with someone who’s a few steps ahead, you don’t want to blindly follow someone else’s path. For me, that’s why it’s also why things are more challenging than just saying, hey, these are the six steps – because I’m not trying to make you into a copy of me, you’ve got a very different business, personality and lifestyle – so that does take longer, it’s a bit more complex, and I hope you will find that’s making your business more robust and meaningful as well.

Terri:                It’s not about just finding it, I think it’s about adapting and evolving with it, because you will change. I mean, I’ve been doing this now about five years since I began to think about branching out on my own. I’m a very, very different person, like in some ways, much more accomplished, but in other ways, still a long way to go. So, just keep checking in, evolving and allowing yourself that grace.

Anna:               And I love that, that grace, it’s so interesting to follow you and so impressive to see you sort of put yourself up and really sort of pivot, I guess, is the timely word and so, and really adapt. And for me, too, and again, I wanted to be nomadic, paddle boarding – and not quite Louis Vuitton and Bentleys, but in that direction. I know what you mean by London, and then now it’s sort of finding a team, and I’ve got a young family, and so it’s just allowing yourself to evolve, allowing the business to grow. And I think sometimes we think, oh, we’ve made that decision and now TADA, we have the business, but that’s not the case. The business changes, the market changes, and it’s going to continue – what are the best things now, I guess, about your work and your lifestyle?

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

Terri:                Perhaps the best thing about my work and lifestyle at the moment is that I’m in control of it. Just before the whole COVID pandemic came in at the beginning of this year, I had been applying for positions, whether in marketing or graphic designer roles, which I was really excited about. I had interviews lined up and to me it symbolised safety. I was like, right, I’m going to get a job where I turn up, I do the work, I learn from them and I get money in return. This sounds great.

They were keen to meet me I was excited to meet them, and then we all know what happened. So, the interviews went from interviews, to telephone interviews, to cancelled. I followed up with them afterwards and they said we’re not hiring now to 2021. And then I’m also seeing a lot of people from university, who, you kind of get the side-eye and you’re like, “wow, you’ve been in the same job since we left uni, you earn quite a lot of money now, you’ve got a mortgage, you’ve got these, these signifiers of success and stability” and they’ve lost their jobs. I’m just like, whoa, the resilience that hopefully I’ve built up over these years is really saving me now, whereas someone who kind of thought they were in it for a while, or for the foreseeable, it’s knocked sideways.

I’m really grateful that the only way out of this is through. The only way to actually make it work is to do the work. So, I think the best part is being in a position to do things I want to do and to be in control, it’s a little bit more responsibility, but to be in control of where my energies and efforts are going is…  well I haven’t woken up and disliked Monday for a really long time.

Anna:               Yeah with that autonomy and having control, it’s all about the freedom… And I think that it’s impossible to overestimate how profound that is, that you’ve just picked up on – as you said, the apparent security of a job. In theory, I think people get it, but I think now, this year, you’ve really understood it. “Oh, I’ve got a stable job, I’m holding onto that” – so you’re scared of leaving that behind to go out into the unknown. But actually, as you said, if you’ve built up a portfolio, if you have the resilience, you’ve diversified your income streams – that is so much more stable and secure than it is to be completely beholden to the company’s (mis-)fortunes, you have no control.

So, it’s just turning the model on its head and I think hopefully more people are working up to it, it’s not too late, and they’re doing something about it, but it is quite interesting shift in the paradigm, and sort of hold on to this apparent stability.

Terri:                I think a lot of more traditionally people like my parents, for example, when I first decided to branch out on my own, my dad was not impressed at all. A lot of that was he’d worked the same job for 45 years. It’s stability. It’s safety. It’s like, you turn up to work, you do your thing, you leave again. Whereas now I just think, because of things that the internet and the opportunities available to us all, it doesn’t have to be that way anymore. You’re actually no safer having someone who could fire you tomorrow or the company could fold and you’d have no power whatsoever. At least this way, maybe it’s just the control freak in me, but at least in this way, I have a better grip on my career, even though a lot of people would think it would be the other way around.

Anna:               And as you said, our parents’ generation, the Baby Boomers, that is what they’ve grown up knowing, and it’s okay, it’s well-meant, but unfortunately the economy and career paths have shifted. It’s not just that it doesn’t have to be that way, it isn’t going to be that way. We aren’t going to have the same… my grandparents had the same job in the same company their entire life. We’re not going to… unfortunately fertility rates are decreasing, we’re not going to have that generous pension waiting for us at 65.

So, again it is just sort waking up to that and re-thinking what we’re going to do. I don’t think it’s being a control freak, I think it’s natural for you to want to have some control over our future and destiny and our income.

And again, just coming back to the so-called stability of a job, I see it again and again, so many people – and I’m not the kind of coach to push people and really challenge them and I think you shouldn’t push people into things, but I do sometimes want to slap someone and go, “no!” shake them and wake them up – it’s the emperor’s new clothes. Because, unfortunately, again, people have been made redundant and then they’re sort of coming back to me and going, oh now I’d like to. And that’s great, but they’ve wanted to do this for the past six months, or even years, and ideally we would have done the work then. I think it’s a bit strange that we wait until we’re forced to do it.

Terri:                It is hard to do the jump. If the people I have met who have kind of branched out and done things on their own, I don’t think I’ve actually met anybody who’s “failed,” but to take that leap out of safety, instability, even if you’ve got a cushion (and I’ve noticed that most of us don’t). I think most of us sort of just have a breaking point. A lot of people just jump and then make the net on the way down.

But yeah, it is hard to take the jump, especially if it’s not needed, you have to have quite a lot of oomph behind you to break out of something that’s comfortable, I guess, like anything in life. You can get off the bus a few stops sooner and get your steps up, but you could also just sit there in the warm and dry. It takes a lot to do the jump, so I understand why people actually kind of get pushed into it a lot of the times.

Anna:               Exactly. And for most of us it’s not that we hate our job… unfortunately some people reach burn out and the pain of staying is greater than the fear of leaving and that is when people say, “Okay, it doesn’t matter that I don’t have savings, I don’t have a business plan – I just need to leave!”

Anna:               But obviously the people I work with, we’re trying to help people lay the foundation alongside of their job, but again, there’s only so much you can do with the time and energy that’s left over to build a whole business – but at least you’re starting to take those critical steps. And absolutely, not to trivialise it, it’s a massive leap to take.

So, the next question is, any advice of course, from what we’ve been talking, but is there anything you wish you’d known say, five years ago? Anything as advice to yourself or someone like you now?

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

Terri:                Kind of sounds cheesy, but I wish I’d known how capable I am sooner. I did a lot of dilly-dallying and hopping on and off the spot and not really going in any direction if you’re going left or right, and just getting frazzled. So, I do wish I’d known it’s hard, but it’s all fixable and it’s all doable, and it all doesn’t have to be done five days ago.

I’ve begun to really settle, especially working with the accelerator over the past six months. I’ve really become settled into the idea of this being the long term game. I think if I was to talk to myself again, five years ago, it would be exactly what we’ve just discussed, in that don’t run and jump right now. Just because you’re not doing it right now doesn’t mean you’re not going to do it, but put like six grand away, rather than leaving with only 600 in the bank. There were some really bumpy landings in that first 18 months.

So, work at things consistently, be persistent and persevere and have patience. You’re not going to see it happen straight away. You’re not going to set up your Instagram and suddenly you’re the next Kardashian, except you’re actually talented. Controversial.

I think that that idea of the long-term game and also having acceptance that you can plan as much as you like, but it’s going to do its thing. Life will come along, whether that’s a pandemic or a market crash, these big things or just things in your life happening. And it’s about having the kind of mindset that allows you to mourn it, go get a cup of coffee and be upset, but then work with it.

Pivot, adapt and understand that you can only control what you can control and you need to keep showing up, but you also need to let go of the things that are out of your control and your mindset and accept the big picture in your, I don’t know if I like to use the word journey because I don’t think there’s an end destination, but your experience will not look like how you expect it to look. I’ve taken several part-time jobs, retail and cafe work and accept that to keep funding the dream, is you need to take a step backwards – but it’s not a step backwards. If it’s taking you closer to what you want, it’s not a big deal. Just don’t lose that perspective and focus on the end goal and keep checking in with that and keep your eyes on the prize!

Anna:               I love that. You’re saying all my favourite things, I almost want to say that I’m so proud of you. You’ve sort of embodied all these things. It’s incredible, because it is exactly as you said, it’s being mature enough to realise, actually, right now, I do want to or need to take a part-time or full-time job for now, and choosing to move back to London or move away, or whatever. Because, as you said, you’ve got your eye on the prize. And it’s not sexy, and it’s not the six steps to success, it’s not, “Hey, I can teach you how to have a launch and in 30 days you’ll have 100 clients – but it is the reality, and it works.

And I love what you said as well about confidence. Unfortunately it’s very difficult to go back and give somebody that confidence.

Anna:               I hope the recording got it. But all I was saying was Terri, I love you and everything you’ve said is so important, so, I hope people have heard what you’ve said and not what I’ve said. Such important insight, so thank you for that.

And I guess with that in mind, you mentioned you are now working as a digital designer for conscious businesses so, if that sounds intriguing to people, where can they find out more about you?

Terri:                So, my website is The best place to contact me would be LinkedIn, which is linked in my name is Terri Witherden. I’m sure Anna will spell that and everything for you because it isn’t the most common of names. And you can also check me out on Instagram at @inkedbytw, although there’s a bit of a side note, I’m currently eyeing up whether or not Instagram is actually worth my investment at this point. So, you may be able to follow along my corporate journeys, if not, they’ll definitely be some surfing and mountains and general Irish craic.

Anna:               Terri, thank you so much for your time. I’m glad I finally managed to nail you down and to hear your story. And of course, yeah, links there if people want to follow along. So, thank you so much for your time and best of luck. Looking forward to talking to you again in a few years’ time and seeing the progress you’ve made.

Terri:                Yeah. And thank you so much for all your support along the way. And you’re a perfect example of having a coach that’s within reaching distance.

Anna:               Absolutely. Thank you.

Terri:                Thanks Anna.


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