Learning to swim
Lessons from a career spent repeatedly jumping into the deep end
Hello - I’m back! It feels good to be writing here again, though I’d be lying if I said it’s without any trepidation. My ‘month off’ turned into a pretty intense one, and as I write I’m still recovering from a very protracted wisdom tooth removal, on a boatload of antibiotics. But I’ve definitely felt the itch to exercise the essaying muscle: if anything it feels necessary, if not right, to dive back in.
During this last month I’ve spent a lot more time on Substack as a platform, leaning into networking opportunities and reading many more articles than I usually manage to. I’ve really enjoyed spending this time here, and it’s taught me a lot which I’m already applying to today’s piece: notably - not to overthink it (one of my favourite pastimes).
I’ve been thinking a lot about my work-life lately and as a result I was intending to write today on what to know if you’re making the move from a big corporate to start up, like I once did. Instead, I found a lot more reflection pouring out about my journey to this point. So I decided to take others’ advice from the last few weeks: I’m publishing as is, even though it could be tidier, could be better-edited, or more polished. At least it will serve as some context for those future posts.
Thanks for being here,
Emma
❤️ PS - If you like this post, I’d love it if you hit the heart so that others may find it too
If you’d had told me fifteen years ago, when I was just starting my career in marketing, that I’d soon be spending seven years helping to build a business (Tyk) from scratch, I’d have been amazed.
Not that it should have been the wildest of ideas to me. My father, a tech entrepreneur, has always had more business ideas than time to execute them: to this day, he still keeps a book next to his bed to write down his latest ideas upon waking. But I also saw first hand the enormous sacrifices required to make a success of those mad dreams, and I wasn’t sure I was cut out for it.
Instead, my teenage dreams revolved around a glittering career in advertising, getting to wear heels every day, and a relocation to New York, ideally. (I was so enamoured with this idea that, six years into my marketing career, when a confused recruiter approached me about a senior account director interview at Saatchi & Saatchi, I went for it, despite having zero advertising experience (which I admitted on entering the room). I very nearly got the job!)
When I fell into marketing at the corporate property giant Savills after a two-week work experience stint, my dreams shifted. I was learning on the job (my degree was more Middlemarch than Marketing) but I saw the ladder stretch out above me and I was determined to climb it. ‘CMO of a FTSE100 company’: that was my new goal.
Until I left Savills to join an actual FTSE100 company (RBS). I took a look around, and at the day-to-day life of the woman running the show, and thought:
‘Hmm. I don’t think I want her job’.
I was twenty-five or so, just four years into my working life, and already I was questioning the route I was taking. I learnt a lot in my time at RBS, and from some fantastic colleagues who are experts in their field. But what I learnt the most was that this environment was not for me.
It was frustrating to come into work every day and have to battle to make an impact. It was upsetting to have a supposedly managerial role but to be given barely any autonomy to execute, let alone make even the most trifling of decisions. And it was almost rage-inducing to have working conversations like the following, which I once had with the corporate brand team about an image for a website page.
Me: ‘Is the traffic light image approved please?’
Them: ‘The thing is, we’re not sure you should use this image, as with traffic lights the light may go red at any moment, and red means stop’.
Me: ‘But it’s green’.
Them: ‘But it might go red’.
I wish I was making this up.
Maybe it was my Dad’s influence or Savills’ very entrepreneurial culture (everything was about making or saving money - they didn’t care how you did it, within reason of course), but already by then I had a very strong sense that time and attention = money. I was totting up the cost of these insane policies and interactions, flabbergasted when I was reprimanded for speeding up a multiple-person process ‘because the Director should have been consulted’. At what cost?
A move to Agency-side changed my life in multiple ways. I wouldn’t have moved abroad if I hadn’t jumped the corporate ship, and I wouldn’t be at Tyk.
The biggest cost in my view was to my morale - and everyone else’s around me. The bank was in its ‘everyone hates us’ period, bailed out by the taxpayer and on an endless carousel of cuts. My second day in the job they announced they were cutting 50% of the department. I survived, my boss didn’t.
By the time the second round hit, I’d already handed in my notice (eleven months after joining), but I was still there to see the axe fall on some of my colleagues. On seeing one return to the floor after her meeting crying, we all gathered around her. ‘You too?’ we asked, concerned faces. ‘No. They want to keep me!’, she wailed.
Not every corporate is the same: the staggering difference between daily life at Savills versus RBS bore that out. Nevertheless, I was twenty-five and hungry for more. I had a ladder to climb, even if it wasn’t the one that led to corporate CMO. I decided I needed a shock to force me into growth, and threw myself into the deep end, applying for a role agency-side at successful London agency Reading Room.
My time at Reading Room (and then Adelphi Digital in Singapore) is a story for another day - in fact there’s plenty of stories there, for plenty of days. But I can pinpoint that that move changed my life in multiple ways. I wouldn’t have moved abroad if I hadn’t jumped (corporate) ship, and I wouldn’t be at Tyk.
Diving into the deep end
As Glennon Doyle reminds us, we can do hard things, and moving from client-side to agency was one of the hardest I’ve ever done. I think it was even harder than moving abroad. I was giving up a (too) comfortable, cushy client-side role to take a significant pay cut, head into the unknown and suddenly have to be ‘the expert’ that people were paying to look to. But scariest of all was my worry - a visceral fear, I recall, that every decision I made would have a very real commercial implication for the business.
That’s the case anywhere you work, of course, but you feel it much more keenly at an agency, where every proposal you wrote and pitched could change the company’s fortune by tens-of-thousands. Where every delayed project, or angry client who won’t renew, is another chip away at the limited resources you have, or the team’s happiness.
What I realise now, looking back, is how much we were primed - and trusted, frankly - to be building a business by those in charge. Of course the senior Directors were running the show, and we followed processes that had been put in place for us to follow, but we were the ones who had to write contracts, run our finances, check our CRM dashboard (which was essentially P&L numbers), and report back accordingly. It was an incredible education, and one which led me to Tyk in many ways - some obvious, others less so.
I remember when I interviewed for Reading Room, my two interviewers - and future bosses - talked about the need for the new hire to jump in the deep end, learn on the job, and figure out quickly how to swim rather than sink. It was scary leaping into an unknown body of water and there was definitely some initial thrashing around. Even some accidental intakes of water at times. But I made it. And when the time came to move on, it was because I was ready for another leap into the unknown. The difference was this time I trusted that I wouldn’t drown, even when the move was ten times riskier.
From over 120,000 colleagues to 16
From 120,000 colleagues at RBS, I’d gone to 250 at agency. When I was approached initially to work at Tyk, the company was just a handful of people. By the time we actually figured out what might work and formalised a job spec and agreement, I would be joining as employee 17. Gulp.
Since then I’ve gone from first marketing hire to VP Marketing. I’ve gone from working practically alone for the first eighteen months to having thirteen direct reports (don’t do this), to now, where we have a CMO and an entire Revenue Operations team supporting us. I’ve gone from an informal 50,000 GBP marketing budget to millions. And in that time the company has gone from the new kid on the block to a recognised Leader in the space, put in the same bucket as AWS, Google, Salesforce and Microsoft. Double Gulp.
And yet, to look back, I can see that all this happened from having the courage - and frankly, the naivety sometimes, to continuously throw myself into deeper and deeper water and learn how to swim to the next milestone: a revenue target, a set of company goals, a fundraise.
Courage creates confidence
Why am I writing this? It’s fun to navel-gaze, I suppose, and like I said at the start, I’ve been reflecting recently on the decisions I made and the moves I’ve taken in my working life.
But I’m also passionate about making sure other people realise they can - and should, go after any exciting opportunity which presents itself, if it aligns with your ideal trajectory.
Many think we require confidence to do courageous work. It’s the other way around: doing something that scares you, gives you confidence.
Think about when you’re asked to do a talk. You feel nervous, you don’t want to do it, even doing the prep makes you feel a bit sick (just me?) But often once you’ve done it, the first thing you think is ‘I want to do it again’.
We can - and should - push ourselves to apply this learning to other opportunities in life. Many people think we require confidence to do courageous work, so they do nothing. But it’s a myth! I’ve learnt first-hand that it’s the other way around: doing something that scares you, gives you confidence. And I want more people to know this. Especially women and other under-represented groups.
Now that’s not to say that there aren’t certain attributes or skills that will mean you’re better placed for certain jumps - there are, and these are ones I want to lift the veil on a little in the next few essays I write.
But if I think back to all the career and life experiences I’m proud of, the thread that connects them is having the guts to say yes, even when inside I’m thinking ‘I have literally no idea how to do this’.
In fact, I’d go as far as to say that you feel the nerves when you know, deep down, something is right for you. It’s not the same as when your gut tells you no.
It’s that ‘ears pricking up’ feeling, or something stirring deep inside of you saying ‘take this shot, as it may not come again’.
What about you? Take ten minutes to ponder or journal the following questions
What have you said no to in the past because you feel under-qualified, incapable, or just a little bit nervous?
What are you saying no to right now because you’re scared?
When have you given a nervous yes that turned out to be an amazing decision?
Track back from the times in your life when you grew the most. What did it stem from?
If you’re comfortable to share, I’d love to know in the comments.
💌 What’s the deepest end you’ve jumped into? Do you regret it? I’d love to hear your experiences in the comments.
❤️ If this post made you nod your head or feel something, please hit the heart to let me know, and help others find it.
📮 Thinking about making the leap to start-up life? In my next post I’ll share the attributes and skills that will help. Subscribe for free and be alerted when it’s published.
I love going on your journey with you. I've told you this before, but I'm in awe of your transformation over the few years I've known you.
What a path Emma!! Love hearing your story, standout