What I’ve learned from having 12 jobs in 2 years

TLDR: I’ve had a lot of jobs in 2 years, since stopping my role as a founder/CEO. From corporates to startups, I've seen and learned a lot. If this is relevant, or you're curious, read on.

Two years ago, almost to the day, I sold my first startup. It was not the dream exit we’d all hoped for. But this is not about that. It’s about what happened to me after… returning to the job market as an ex-founder/CEO. The transition back into a salaried role is not something I’ve found easy. I know I’m not alone in this. It is, without a doubt, the single thing people in my network ask me about most.

‘Interesting’, ‘unusual’, ‘brave’ and ‘inspiring’… all words people have used to describe my CV. I'm not particularly proud of this much change, but it has given me a lot of perspective and knowledge. And, whilst I’m hardly a career expert, if my learnings can help other recovering founders take their next steps, then that is great. There is a life after being a founder, and it’s honestly not that bad. Chances are, if you’ve been a founder, you’ve been through worse than what comes after.

Lesson 1: Don’t rush into anything - if you can take a break

I did not get rich from my startup selling.

Far.from.it.

So, I needed to work pretty quickly. However, I still took a 12 week break when I stopped. I went to Argentina.

We were in the middle of the sale closing when I arrived. It was not a stress free time. When I landed, I remember I still felt like a complete failure. Nothing anyone could have said (or did say) could have changed that at that point. I felt guilty, ashamed, like I was not good enough, and profoundly confused about what I would do after this. In the first few weeks of the trip, I did a lot of walking. Often alone, usually in silence. I began to realise the narratives in my head could shift, from those of self loathing to ones of greater self compassion.

By the end of that trip, I still took total responsibility for everything that happened, but like a mantra I started to say that I was “rich in learning”. This described the first time founding experience, and was a big part of how I was able to process it. And it’s true. You are rich in learning, and you’ll take your broad experience into whatever you do next. It will be hugely valued in future, even if it doesn’t feel that way at first.

Lesson 2: Think carefully about the stage of the company you want to go back into

Few people know this, but I had a job as a Chief Product Officer of a D2C startup by the time I got home from my break. The founders were lovely, the product was cool. It was also in the middle of a seed funding round - the exact point in my business’s history where I’d chosen to take a different path. I didn’t think about this at all, because I was in a rush. I’d been in many D2C seed stage startups, I felt quite comfortable in small teams. I thought this would be perfect. But… it was not.

These people did not get the best of me, by any stretch. And I quickly told them that this wasn’t the right environment for me. They were understanding and kind, and I think in my short tenure we learned a lot as a three. However, looking back now I should have known I’d find going back in at this point triggering. So… onto the freelance market I went…

Lesson 3: Freelancing can be a brilliant way to try things when you’re not sure on the role you want

Most founders are generalists. Founder CEOs are almost certainly generalists - who may have had to run every part of their business at different points. The most common question I get asked is “how did you know which roles to apply for?”

I didn’t know, so I chose to freelance for a bit. I thought, and to an extent I still do think, that product was the area I wanted to focus on. But, I’d also done a lot of operations in my time. Truth be told, I didn’t really have a clue applying to mid/senior roles felt almost disingenuous.

Freelancing can be a good antidote to this. Expect your first roles to come from people you know. You can try things, without overcommitting to a team or a role. I absolutely thought I would freelance to test out companies before I then joined full time. That was the plan. That did not work.

But I met loads of people, tried different sectors, tried different roles and it was great for me. I learned a huge amount seeing different founders in action, and different operating models. Both good stuff, and less good. This added to the feeling I was ‘rich in learning’ - but I still did feel a little lost when it came to my ‘career’.

Lesson 4: If you freelance, get to know some other freelancers

I was lucky, a number of very good friends were freelancing at the same time as me. In engineering, sales and growth. This helped me validate pricing, understand positioning, and also to get referrals into jobs. In the best best cases, I worked alongside some of my best professional friends. This gave me a real joy for work again. Something which I'd struggled to remember.

Freelancing can be lonely. It definitely made a difference to me to have people I could call to talk through issues and opportunities. I’d also strongly recommend getting a co-working space once you win a few contracts too, as this allows for widening your network.

Lesson 5: Try to speak to other ex-founders

Sometimes, on this road of career experimentation, I felt really lonely. Like I was the only person who just couldn’t decide what they wanted to do, or which jobs to apply for. One thing which helped a lot was meeting other former founders and CEOs.

I was lucky to meet a lot of epic ex founders and CEOs in the last couple of years, through events and Linkedin. They were also exploring different careers and doing freelance work. Talking to them helped me to understand that it is genuinely hard to decide what you want to do after being a founder and made me feel less alone. You also get to hear their own inspiring journeys, which is often a chance to gain more perspective on your own journey. I can’t tell you how much hearing other people’s stories helped me to better understand my own, and be kinder to myself.

Lesson 6: If you want to stay freelance, productise your offer

I didn’t really want to stay a freelancer at first. I wanted to find a permanent role. However, I did get some very good advice about productising my offer if I was going to stay freelance. And now I’m seeing this everywhere i.e. the “Fractional CXO” (sidenote, other products are available...) Some people are doing this so well, and probably making bank! Again, I did not do this. I did a pretty random smattering of projects during my 9 month stint. But had I decided to invest more in freelancing, I was sure that this would have been the way to go.

Lesson 7: Grill your future employers (and reference them too)

By the time I’d been consulting for 9 months, I was getting bored. Boredom has always been a dangerous place for me. I can be impulsive. Me and my brother actually used to say to my mum as children that we were ‘dangerously bored’. Well that was me, by the end of 2022 I was dangerously bored of freelancing. I wanted to commit to a big vision. I craved stability. I wanted to work with a team again. I wanted to learn from other people. I wanted to be taken under the wing of a great (female) leader and learn how to be the CEO I failed to be.

This was the point that my first corporate job opportunity landed in my lap. The person landing that was a woman who I admired so much (see lesson 7). And I was just ready to hear exactly what I wanted to hear from the interview process. Health sector ✅, big new shiny role ✅, big budgets ✅, build my own team ✅, great manager ✅, ethical ✅… the list goes on! So, by the time I had the offer I was sold on my new corporate life. Get a mortgage, be a grown up, put those hard founder years behind me.

What I didn’t do, was go through the fundamentals of that business. Properly examine the culture, org structure, financial position, understand the leadership dynamics. All stuff I’d encourage anyone to try to get from an interview process, and want people who I’m interviewing to test me on. Particularly anyone who is taking a senior role. You can offer to sign NDAs etc. Given that your role in any large organisation is going to be a mixture of sorting the biggest issues and improving the P&L it’s pretty stupid to take a role without that stuff. I didn’t do this, because I just saw what I wanted to in this job. This was actually so dumb, and I cringe hard at this now.

I think a lot of people are scared to really grill people with the tough questions during an interview. And that’s understandable. Not everyone will like it. So I’d suggest landing the role (so they’ve decided they want you) and then spending more time on this stuff than I did.

Whilst I imagine I’d have still taken the role had I done this, I would have thought more seriously about the offer for it to be a freelance position. It was a very big decision for me to move from only having worked in preseed to series A startups, to go to a 150 year old corporate. De-risking this with more optionality would have been sensible. But… I was dangerously bored, so I just went fully in. And I only have myself to blame for this.

Lesson 8: Don’t expect your line managers to be the leader that you felt you weren’t as a founder

After “what role will I do”, the second most common thing ex-founders say to me is that “they want someone really great to learn from”. After all, we all ‘made so many mistakes and have so much to learn’ after our founding journey. And yes, I do believe this is usually true. However, be careful about pinning these lofty expectations onto a single person. I did this completely with one of my managers - Katie. She was the fearless, female leader I’d craved for so long. She was going to teach me how to be a better leader. Katie was the answer to all my professional development needs.

This was completely unrealistic. No single person is going to be a source of that. And whilst I say that your line manager is going to be the most important person in your future role, they’re also just one person. As ex-founders you’ll often bring a totally different perspective into an organisation, and also often to your managers (who may have never managed a former founder before). It’s a 2 way exchange process. You’ll help them, they’ll help you. It’s not fair to put all the pressure onto one person, as they’ll always have a lot more than just ‘your development’ to focus on.

What ensued for both Katie and I was a destabilising environment, through circumstances beyond our control. We had to each support each other through abrupt changes, and the roles not manifesting as we’d hoped. I learned loads from Katie, but it wasn’t the “teacher” relationship that I and so many other ex-founders seem to crave. And that will rarely be one single person, but it should feel like your senior team are all teaching you to level up. That, for me, is a high performance environment. And certainly what I look for now.

Lesson 9: Think about what really motivates you (and then think about it even more again, and again, and again)

For me - it’s progress. I’m not patient, I want to get things done, I like to create a lot of momentum in organisations, and I will apply pressure to get things done quickly. It’s who I am, and it’s what I enjoy. It’s definitely a weakness, as well as a strength. But in startups, it’s generally more of a strength. I over-indexed on this even more after the failure of my business. Looking back and feeling I should have acted with urgency to sort out issues.

It took both a role where I couldn’t make ‘progress’ (to my own standards), as well as a role where I could make huge progress to recognise how important progress is to me. I’m not a perfectionist, I strongly believe done is better than perfect. But if I can’t make anything happen, I’m like a caged bull.

A short cut to identifying your motivations and strengths might be to ask 5-6 people you’ve worked with for some honest feedback on what you’re like. I’d recommend asking people who’ve managed you, peers and people you’ve managed. Look at the consistencies, and the differences, and work out what your ‘spike’ is. As you won’t be working with them, it’ll be easier for them to be really honest. I tried to ask everyone I consulted with for direct, negative feedback so I could keep learning about myself.

Lesson 10: Think about your specific strengths within the organisational structure you’re about to join

I should have thought more carefully about my personality in a very established, corporate way of working. Before I started my first corporate job, someone I really respected and rated told me “don’t make any decisions in the first two months, just get to know everyone and understand the different relationships at play”.

This was, with hindsight, excellent advice. I did not listen to it. Not because I don’t listen (I thought about this a lot). But I am impatient for progress to a point where it’s a fault. I was so keen to make impact, that I just jumped in, full guns blazing, with a total naivety. And this… probably didn’t help me overall.

Whilst I do think some people loved my style (I’ve never been called ‘refreshing’ so many times…), I also know that I annoyed a lot of people. And I question whether my impact overall was positive, or negative. Looking back, I was just so frustrated by the change of pace. I made a lot of mistakes in this 6 month chapter.

There are definitely places in-between established corporates, and small startups, which would have been a better place for me. Again, I am rich in learning though…

Lesson 11: If your interview sounds like a VC pitch, probably not a good sign

Most VC pitches are about putting the absolute best light on every single part of the organisation. That’s the game. Job interviews should not be like that. Most roles are a version of sorting out all the things which aren’t working. So it’s best to get an idea about them before you start.

If it’s an amazing company, then maybe you’re job will be about making sure the business stays on top. Also really, really hard. You’ll have to see round corners, and know the market. Also good to establish if that’s organisation/founder needs from you.

Sadly, founders in pitching mode can sometimes treat job interviews like a pitch. This is such a red flag. You’ve gotta get past the pitch. And as a former founder… you know that. As per lesson 6 - grill your future employers. An even better sign? A founder who can be honest, direct and up front about the challenges you’ll need to deal with from the start.

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These 11 lessons might sound like a stressful list of mistakes… and for sure, that’s partly true. But it’s also been incredible to:

• Get so comfortable with change, something so many people don’t like

• Meet amazing people, and build my network

• Gain experience of larger organisations and teams

• Work in many different markets

• Execute on GTM in new areas of healthcare like insurance, B2B2C and pharma

• Get feedback (bad and good) from so many different people along the way, which has made me more aware of myself

• Build a much broader set of perspectives on leadership.

I could go on…

I hope if you’re reading this, and you’re unsure of what to do next, that this has helped in some small way. It's confusing at first, and maybe I'm still confused. But you will be fine. You've done harder things!

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All my views are purely my own, and don’t represent the organisations I’ve worked with in the past or am currently working with.