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Career Off-Roading: A Professional Journey Without a Map

Want to take charge of your professional development and advance in your digital career? 

In this blog post, guest speaker Allegra Chapman (Founder of Brighton Digital Women) talks about her journey career off-roading, expectations vs reality, and tips and tricks she learnt along the way.

I have had a somewhat unorthodox career journey. When I was preparing to leave school, my concept of a career path was something like this:

What actually happened over the next twenty years looked more like this:

I spent a long time worrying that my professional journey hadn’t been linear or focused enough, that I had worked in too many different roles and sectors, and that I had spent far too long not knowing what I wanted to do. But after working as a journalist, fundraiser, editor, marketer, freelance consultant and, now, business coach and strategist, I have come to realise that my varied CV is a major asset.

Potential employers, clients and collaborators have all commented on how much they appreciate my breadth of experience, skills and knowledge. I’ve been lucky enough to make valuable connections with a variety of awesome people, and, possibly most importantly, I have had an absolute blast!

Finding a compass

The most important thing I have learned from my long and winding career road was that doing what you love will always lead you in the right direction. Each choice I made along the way was motivated by joy – I wanted to do more of the things that made me happy. 

As time went on, I found myself increasingly wanting a sense of fulfilment and purpose in my career. Purpose and happiness are the foundations of successful careers and businesses – they drive productivity, increase motivation and outperform the competition. The longer we spend in careers, the more we begin to look for that sense of purpose that will sustain us and push us forward. 

After a year of soul-searching, I came to realise that my sense of purpose came from helping other people find theirs. I began working with growth agency The Joyful Web as a coach and strategist, helping business owners to identify the purpose behind what they do and embed that within their business strategy to drive meaningful growth. 

What is fantastic about this role is that it has brought together all the experience I have accumulated over the years, all the skills and, most importantly, all the things I love.

As long as you follow your heart, you can’t go far wrong. It all comes together in the right place in the end.

Piecing together the map

After twenty years of stumbling around blindly in the career wilderness, I have learned a few things that might be of use to others trying to find their way.

Follow your heart

As I said above, do what gives you joy, trust your instinct and do what feels right. If it makes you happy, it’s the best choice you can make.


The only way to know what truly makes you happy is to try different things. See if you can try out different elements in your current role, try secondments, volunteering, training, ask if you can shadow someone… test things out to find the ones you enjoy.

Take the leap

Stop agonising about whether you can do the role you really want. Go for the next step up, take on a new challenge, try something different - if you think it’s something you’d like to do one day, do it right now (or find a way to do it tomorrow if you need more of a run-up).

No one knows everything

Too many people hold themselves back from taking that leap because they’re worried that they don’t know everything they need to know right now. But you’ll never know everything. No one does. If you know most of it, you can learn the rest on the job.

Know what you don’t want

Knowing what you don’t want can be just as important as knowing what you do want. Ruling out the things that make you unhappy will help you zero in on your ultimate destination.

Your needs will change

When I was in my twenties, I loved working in events roles where I was out late in glamorous locations several nights a week. These days, I’m in my mid-thirties with a young baby, I don’t drink and I go to bed at 9pm most nights. Those previous dream jobs have become my idea of hell. I struggled for a while with accepting that who I was had changed, but it’s inevitable that you will change and perfectly reasonable for you to ensure your role and career adapts accordingly. It can, and it will.

Know what you need

It’s tempting to get caught up in continuously trying to move up to the next level and get into the next salary bracket. But moving up for the sake of it won’t necessarily make you happy. How much money do you actually need to live a good quality of life? Focus on making sure that’s covered then you’ll be in a better position to make the money you want in a way that brings you genuine joy.

Create opportunities

If you can’t find the job you want, create it. The company of your dreams might not have the role you want because they haven’t realised they need it yet. So tell them they do, and why you are the person to do it.

Take advice, not instruction

By all means take input from teachers, parents, friends, random people you meet at the bus stop, but they can’t tell you what’s right for you. They can give you advice, but you can also ignore it if you want to.

Connect to your purpose

As I said, we all need that sense of purpose and fulfilment. That doesn’t mean you have to be saving lives or rehabilitating donkeys. It just means that your job allows you to live the life you want and that you feel good about what you do, how you do it and who you do it for. That’s not only going to make you happy, it’s going to make you better at what you do. It’s a win-win.

As Sheryl Sandberg said in her book Lean In, “Careers are a jungle gym, not a ladder.” So don’t get caught up in going in a straight line just for the sake of it – experiment, be playful, follow your instincts and see where you end up. Enjoy!

Want to watch Allegra's talk?

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