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How knowing my WHY completely transformed my career, twice


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When I first started my portfolio career, I was armed with an arsenal of graphic design and branding knowledge, a desire to champion the weirdos of the world and an unparalleled strangeness that spoke to a new generation of entrepreneurs.

Now, five years in, I’ve built (and exited) a business I can be proud of and am transiting into the next phase of my maverick founder journey. So, in traditional end-of-year style, I’m taking a moment to reflect on that epic odyssey and share with you, my lovely fellow portfolio professionals, how constant reflection and an understanding of my WHY got me to where I am today.

Let’s take a quick trip back in time

In the summer of 2020 I was stuck in a rut. At the time, I was freelancing as a graphic designer – and let’s be honest, I was good at what I did. I had a nice website, a solid logo and some splashy business cards. It was all very fine, inoffensive and unbelievably boring.  

The work was creeping in, the invoices were being paid and I still had a roof over my head, but I wasn’t excited and that lack of drive is hard to ignore when it starts to cloud every waking moment. I knew there had to be something more; something that left me feeling energised and fulfilled.

Afonso Pereira © The Portfolio Collective 2023

Thankfully, I had started working with a business coach. During one of our sessions, she told me we were going to work on discovering my WHY.

“What’s one of the biggest challenges you’ve faced in your life, overall?” She asked. Really, she was introducing a larger topic – why I was put on this earth in the first place. 

I replied, “I’ve always felt like an outsider; like I don’t fit in anywhere.”

A penny dropped when I said that out loud. Partly because I had no idea where it had come from, but mostly because it really was true.

The fact is, I’ve always been a bit STRANGE

As a teenager I was the awkward, lanky kid that towered over everyone at 5’11, while music ranging from Slipknot to Abba to Kendrick Lamar blared from my headphones. To this day, I’m regularly asked if I own a single item of clothing that isn’t black. 

If you walk into my flat you’ll see I have an impressive collection of Star Wars and Batman merchandise for a woman in her thirties. I could go on about all the things about me that make people say “really!?” for hours on end. But it is the quirks and weirdness that make me who I am and help me stand out from the crowd. 

A few years ago I hadn’t accepted any of these quirks; I hadn’t even acknowledged how meaningful they were to me, and how much they shaped my identity.

I spent most of my career hiding behind a generic, ‘Linkedin appropriate’ personality. I knew then it was time for a change. During that coaching session, I discovered my WHY, and I summed it up in a mission statement that gave me chills:

To inspire and champion the underdogs, outliers and renegades to carve out their place in the world.

If you aren’t familiar with what a mission statement is, it’s basically your aims and values distilled into a profound and memorable sentence (OK, ‘profound’ may be a bit of a strong word, but it doesn’t hurt to aim for greatness!).

So take a moment to think to yourself, “what impact do I want to have on the world?” And then figure out if you’re working towards that or if you need to change something to make that dream a reality.

It helps to keep a record of how you feel at the end of each day and pinpoint any common threads. Do this for a month and see what you come up with – it may surprise you. Just twenty minutes of reflection and stream-of-consciousness writing can result in some amazing truths. For me, coaching was the mirror I needed to hold up to truly see myself, but everyone’s process is different.

Recognising when it’s time to make a change

In what was one of my most terrifying (but exhilarating) career moves to date, I decided to take a huge leap into the unknown and launch a design and branding agency: Strange

Strange took on a life of its own at a rate I never could have imagined. Suddenly I went from watered-down and overlooked to a force to be reckoned with. I had messages from strangers telling me how my story had inspired them, others mentioning my name in rooms full of opportunity, and everything took off. 

I worked with some of the coolest, kindest, most fun humans I’d ever met, and we got to create beautiful things together. For a long time it felt like I was on exactly the right path.

Fast forward to a few months ago, and I felt that familiar lack of purpose start to creep in.

After plugging away at Strange for three years, it hit me that the business model that I’d chosen could only realistically serve companies with decent budgets. Without meaning to, I’d fallen back into my old problem. 

If a done-for-you brand design was my HOW then I was missing out on reaching the very people I’d vowed to serve. I had lost the connection to my WHY.

I’d fallen back into serving the big companies, not the underdogs or the outliers. I wasn’t there for the people who needed me the most.

Career creep is a common problem many people face. It’s not easy doing what you love, and it takes a lot of bravery to dedicate your life to it. If it goes well – and I hope it does for all of you – then there’s the likelihood of your vision being dwarfed by the momentum of success.

My advice? Take a moment to think about what success means to you. If it’s seeing your business grow fast and making lots of money, then that’s great. But for me, success was intrinsically linked to my mission. So I needed to come up with a new model that allowed me to be successful financially in a way that spoke to my values and purpose.

It’s OK to pivot. In fact, I encourage it.

I was having more and more conversations with those people who loved everything Strange was doing: the messaging, the brand, the ethos. But they couldn’t afford to work with me. 

To remedy the problem, I started to create low-ticket solutions for that crowd: courses, PDFs, anything I could think of. I started my podcast, Build Your Maverick Business to share tips, advice and real stories that transcended design and branding. Organically, a new career path was starting to unfold in front of me.

I Build your Maverick Business | Podcast trailer

Then one day, after a particularly painful client call, I had the terrifying epiphany that Strange just wasn’t my vehicle anymore. I had to let it go. 

I realised I wanted to lift up the people who had dreams, ideas and a whole load of creativity, but not much in the way of business savvy. I wanted to reframe the entire entrepreneurial space in bite-sized pieces for those people, so they would believe it was possible for them too. 

If I could build a business that I loved, then I could show other people how to build something they’re really proud of, WITHOUT following the rules. I realised I wanted to show people how to embrace their authentic selves, how to make their personality shine through and build their own maverick businesses. 

For the second time in three years I took a huge leap of faith and pivoted in my career, parting ways with everything I’d built up until that point. I made the decision to shut my agency down. 

Afonso Pereira © The Portfolio Collective 2023

The emotional impact of a big career change

It was terrifying but exhilarating at the same time. As soon as I said the words out loud, I felt a rush of emotion and knew to my core that it was the right thing to do, no matter how scary it seemed. 

I’m now creating a maverick academy, filled with information, resources and activities to help even complete beginners build their own rebel empire. I’m right back at the start of my journey, with no idea how it will all unfold, but I couldn’t be happier!

I finally feel like I’m completely aligned with that WHY, and I can’t wait to help my underdog crew to carve out their place in the world. 

Yes, change is scary. But fear is often a good thing. It’s a motivator and a lens through which we can discover amazing things about ourselves. If you’re thinking about a career change – or feeling stuck in whatever stage of your portfolio career you happen to be in – I advise you to embrace the entire array of feelings bubbling in the pit of your stomach right now and do some serious self-reflecting to figure out what your next step will be.

Think you’re ready for a big shakeup? First, ask yourself a few questions.

I know my story isn’t the same as everyone else’s, but that doesn’t mean you can’t recognise yourself in the struggles and successes that I’ve had. If you’re itching to make a change and know you’re not on the right path, here are a few key questions you can ask yourself to get back on track.

What would you be doing if money weren’t an object?

Money is just one consideration in any career, so passion and fulfilment should be pretty high up that list too. Is there something you daydream about that could become your reality with some support or short-term pain?

Can you think of a day in your career when you felt like you’d have happily worked for free?

My podcast had been running for a year without any monetisation before I decided to grow it into my full-time gig. I loved every second of it! If there’s something you’re truly passionate about, regardless of what money you make from it (if any), it’s worth exploring.

Are you keeping yourself unfulfilled by sticking to what you know?

In hindsight, my HOW and WHAT were rooted in graphic design because that’s all I’d known up until that point. Is there a career option that you’d love, but you’re discounting because it seems too far removed from your current experience? Don’t be afraid to throw out the rulebook and retrain.

Are you letting fear of the unknown hold you back?

Change is scary, and entering into a new industry or area of expertise can feel like stepping off the edge of a cliff and hoping a net will appear. However, there is absolutely nothing scarier than looking back and wishing you’d done things differently.

There’s no way of knowing what will come next for Build Your Maverick Business, but for now I know without question that I’m on the right path. My WHY has acted like a north star, guiding me in the right direction even when things felt chaotic. 

If you too have found yourself a bit stuck and uninspired by the work you’re doing, it might be time to ask yourself the tough questions, break free from the familiar and venture into the unknown where the most fulfilling and authentic version of your career awaits.

Need help figuring out that WHY? Why not come along to our next Personal Branding Masterclass (led by myself and the amazing Fiona Chorlton-Voong). We’d love to see you there!

Think this sounds like the right path for you? Come along to our monthly Get started event for new members to find out what a portfolio career could look like and how The Portfolio Collective can help you take those first steps towards professional success – and don’t forget to connect with our community!

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