Courageous Shifts – Navigating the Leap from Corporate Leader to Startup CEO

I’m Katie and almost 4 months ago (Jan 2023) I made the bold move to leave the relative safety and security of the corporate world to join a startup.

In this article I am going to share 4 key things I’ve learned so far.

This article is designed to help those of you considering a similar move and those already there. It will not tell you how to run a startup, how to identify customers, or define product needs. Instead, it will focus on what we as leaders can do to set ourselves up for success, whatever our personal definition of success may be.

I write today as a work in progress. The things I’ve learned and unlearned change every day. I also write today as a neurotypical, cis-gender, white, person without a disability and therefore that privilege is consciously and unconsciously interwoven into the things I highlight. My hope is that by sharing my personal experience you might find a useful nugget to help you in your exploration towards career fulfilment wherever that may lead.

Get ready for hard work

So, let’s start with the reality. Leading a startup is hard. Really hard. It often involves more work and less pay. In my almost 20-year career, I’ve lived and worked all over the world in various roles and this is by far the biggest career change I’ve embraced to date. It’s demanding and it’s lonely. There are days when it doesn’t feel worth it. There are days I would go back in time and make different decisions. Today I am not going to debate whether this was, or wasn’t, the right decision for me. The decision has been made; so I have an opportunity to make it the right decision and move forward positively from here. In case any of this rings true for you or sparks curiosity, here are my 4 tips for navigating such a significant career change. My hope is that it inspires you to believe in yourself a little more and go after the things you truly want.

Tip 1: Define your why - both before and after the move

I’m sure you’re all familiar with Simon Sinek who talks extensively about this. This is not about identifying the company’s why, but rather your own. Specifically connecting with your intrinsic motivation. Not what looks good on paper, or society tells you that you want, but what you really want. This may be especially important in instances where you join as a late founder (as I did) and need to triangulate your own purpose with the company’s mission.

Do you already know your why?

Sometimes it can feel as if everyone already knows their purpose and you are left knowing you want more but unsure what that means. If this is the case, then I often use exercises called Best Possible Selves or Ikigai (a quick google will tell you more) with my coaching clients to get closer to this. Or perhaps it may be easier to start with what you don’t want, or don’t like about your current situation, and then flip it to see where you land. Knowing your ‘why’ doesn’t necessarily mean you’ll have all the answers or a 5-year plan. It could even be a simple word or feeling you wish to pursue.

You don’t need to have all the answers

Identifying your why (however big, small, clear or confused) will be critical to know whether a jump to the startup world could be right for you and is also critically important once you land. Startups are usually less structured than corporates with fewer people doing a broader set of roles. As such, a startup will pull you in so deeply and in every different direction. If you’re not careful it can pull you under, leaving you detached from your own purpose. For me, this looked like completing the monthly accounts at 21.30 on a Friday night trying to work with a system in Dutch – not the reason I get out of bed in the morning and certainly stretching my Dutch skills beyond their limits. Of course you need to prioritise business objectives, but you also need to find a balance with your own personal objectives. Fortunately, whatever role you currently hold, getting closer to your purpose can be achieved through a practice of job crafting whereby you co-create your role to align it more carefully with your skills, passions and values. This been shown to increase wellbeing and improve job performance.

Supporting others provides deep purpose

In my case, I have known for a long time that I wanted to help people heal and lead fulfilling lives. Up until now I have focused on this through working with private coaching clients and participating in wellbeing and diversity networks alongside my corporate role. Although wonderful, this wasn’t enough and the voice inside my head kept getting louder and louder, telling me I should be doing these things full time, not just on the side. I knew moving to a startup would involve a lot of hard work, but I was used to that. Whilst plugging hiring gaps in my team, I was used to a punishing corporate schedule. Coupled with this, I recently completed a masters degree alongside a full-time leadership role. Both these things were very hard but taught me that hard work is manageable when you are connected to purpose. Yes, there were days when I resented these demands on me (especially when friends were out having fun and enjoying the sunshine), but I loved supporting others and acquiring new knowledge, so overall it gave me more, rather than less, energy.

Practical Balance

After an initial punishing first few weeks at the startup, I knew I needed to find this balance in my new role. It isn’t always easy because in a startup there are always a million things to do, and each decision typically has a bigger impact than it would in a larger company. Practical steps that I put in place were to block out time in my diary for content creation, connecting me directly to my passion for DE&I. I work each week to identify my glass balls from my regular balls (the former I cannot drop) to keep me focused, and I take stock to consciously recognise the things that I am proud of / enjoyed. Sometimes I even have to remind myself that I’m the CEO and therefore if I want to do something I am allowed to!

Tip 2: Take the next 1st step

This is an approach that always serves me well when I am feeling overwhelmed. Chunking down goals into manageable sub goals is also something I often support my clients with. It holds true when considering the leap to the startup world and once you’re in it. Everything can seem impossible but very often the next 1st step is possible and doesn’t require any big commitments. So, take the interview, meet with likeminded individuals, say yes a little more. The reason I am writing this today is because I made a series of small steps. I could never have done this otherwise. My journey started in a cold classroom in a leisure centre in the UK contemplating whether I could train to become a PT alongside my then corporate job. Tired of spending a lot of money on my own PT, I figured I already knew quite a bit after years in the gym and I wanted to do something that had the potential to help others. At the time, I looked at the commitment needed alongside work, and decided it was too much. Instead, I opted for the shorter version, the gym instructor course. Once completed and after a little rest, I returned to complete the full Level 3 PT certification.

Why am I telling you this?

Well because this was about much more than becoming a PT, it taught me I was capable of achieving new goals alongside any leadership role. This gave me the confidence to apply for a much bigger challenge, a masters degree alongside a new corporate job. Having set the new behavioural and neural pathways to take on additional challenges, the decision itself was a quick and easy one. I had the data to prove I could do it. Slowly but surely, I was putting in small steps towards my purpose which led me to starting my coaching business and eventually making the jump to Enliven.

Figure out the questions you need answers to

Looking back with the power of hindsight, I wish I would have made a move earlier. For some people it feels right to jump in headfirst. I’ve done this at Enliven but this isn’t my usual MO. I’ve spent my career in analytics and strategy, so I love to consider all the outcomes and the action plan associated with them. When considering the move to Enliven I needed a plan. For example, can I afford this? What are the risks? What’s Plan B? I sat down with husband and reviewed the financials to see if we could afford it and to identify any cutbacks we would need to make. I went back and forth; I can do this; no I can’t do this; I must do this; eventually to, can I do this? Depending on your level of seniority and compensation, moving to a startup is likely to have a significant impact on your salary. Therefore, perhaps you first want to explore greater purpose with the freedom of a corporate income. I wish I had been brave enough to do this. If I could go back in time, I would ask to go part time and take one day off a week. At the time, I told myself that I couldn’t do that as I’d end up working full time for less pay, that it might negatively impact my career, plus several other limiting beliefs. The reality is that I absolutely could have done it. I just didn’t believe in myself enough to know I was capable of more, and importantly that I deserved it.

If you had 1 day a week to pursue anything you wanted, what would you do?

In my case I found Enliven whilst relentlessly reviewing the job section on LinkedIn. I was deliberately trying a variety of search terms to see what delights I could find. Then, as if it was a gift from the universe, I got lucky. And you might too, or perhaps you want to start something from scratch?

What would you do if there was no such thing as the right decision?

I was once listening to an Olympic sailor talking on a podcast and she shared that in sailing, unlike many other sports, you don’t have real-time data to let you know how you are performing and what you could do better. Therefore, once she makes a decision, she can’t worry about whether it was the right decision. She simply must make that the right decision and make the next ‘right’ decision from there.

Deciding whether or not to make the move to a new career is only going to be the first of many more tough decisions (despite tip 1, working in a startup isn’t just wafting about, high on purpose). Now here in the startup space, I find using the approach of identifying the next 1st step just as useful. There is so much to do, often no one to do it and no one clear path to success. So just like a sailor, I keep identifying the next 1st step and go from there.

Only you know if this is right for you and only you get to decide.

Tip 3: Find your community

Perhaps this should have been tip 1 as this is the most important. According to Brené Brown we are hardwired for belonging. Regardless of whether we lean more towards introversion or extroversion, we simply cannot do everything alone. Years ago, being isolated by one’s tribe was a death sentence and even today with all the possible connection tools, loneliness remains a fatal epidemic.

Throughout my career, being part of and/or leading a team has been my main motivator. The best jobs I’ve had aren’t necessarily the ones where I have progressed the quickest or earned the most money. The best jobs have been where I felt part of a community and genuinely cared about the people I worked with. Coming into a startup the teams are often smaller, and due to the necessity of focusing on other things (such as financing and launching), a strong effective culture may not yet be in place. This can make things feel lonely, whatever role you hold. As a corporate leader I have been lucky enough to find ways to surround myself with high performing and/or high potential talent, making it almost effortless to delegate. In a startup, due to size and maturity, delegating may not always be possible. You’ll need to be ready to do more, get stuck in and likely rely on google and chatgpt as extended members of the team!

Be your beautifully diverse self

Additionally, walking into the startup world my first thought was, where is the diversity? Having worked in STEM my entire career I am used to being one of only a few women in a room. However, moving into the startup world I very often became the only woman in the room, and additionally all the faces were white. It felt as though I was expected to assimilate into the ‘traditional CEO’ which in my opinion was associated with many masculine behaviours in terms of how to lead and how to sell. There is nothing wrong with masculine behaviours, it is simply that they do not fit me, and I suspect that is true for many others, across all genders. My first gut reaction was to think, “nope, I’m out, I don’t belong here”. However, I knew I was more than capable to do the job ahead. I also realised that this was about more than me. If those of us who look, feel, and think differently always run from spaces ‘we don’t belong in’ then we’ll never belong. Instead, we need to use the opportunity to change those spaces to make them more diverse and inclusive so that more of us can find our place.

Don’t be afraid to ask for help

Therefore, with all this in mind one of my first words after joining was “help”. Help is arguably the most powerful word any one of us can utter. As a CEO in a startup, you are asked to do many broad things, but it doesn’t mean you need to have all the answers yourself. Very quickly I assembled a diverse network to support me. Professionally I have multiple mentors across genders, experiences and locations. I specifically sought out female mentorship within the startup investment space and the corporate space; mentorship from successful startup CEOs who understood the challenges first hand; and I welcome all the guidance offered from our generous and supportive investors. As well as my professional and intellectual support, I continue to believe in the importance of looking after the whole person, and therefore I also checked in again with my therapist, coach and somatic coach, in order to be the best version of my (workplace athlete) self.

Tip 4: Let Go

Somewhat in contrast to the first three tips which are focused on taking an active approach, this one is about the opposite. It’s about not trying to control everything but instead letting things flow.

It’s really about getting out of your own way.

Personally, I find this the hardest of all the tips, especially when making a big change, because it feels risky and therefore scary. Perhaps this comes naturally to you. Indeed, I have many friends who find this natural and easy, as even I have at times in my career. If so, that’s great. Keep doing you. If not, perhaps there will be a useful nugget for you here.

To make such a significant change from a corporate to a startup, we need rethink our playbook. Within the corporate world there are many rules and expectations, both conscious and unconscious. These may not apply in the startup space. When making such a change, you have the opportunity to leave any corporate baggage behind and start afresh. Sure, the start-up world is just as political and capitalistic as the corporate world (even in the positive social change space), so I won’t pretend it’s a paradise, but at the start of anything new, you have an opportunity to press re-set and let things go that are not serving you.

Define your own success measures

Importantly, in a startup, you may get to choose the metric by which you measure yourself, or at the very least, have highly objective measures such as revenues or client numbers. Conversely, within the corporate world, we are often bound by performance review processes and frameworks which, in my experience, can be highly subjective, unclear, and therefore not always used to get the best from people. It’s likely from such a corporate process that you’ve been told things about yourself, in terms of who you are, and how you lead. Firstly, no one can tell you who you are (no matter how senior the person is), you are the expert on you and don’t let anyone tell you otherwise. Secondly, consider how true and helpful the feedback is, especially in your new surroundings. Feedback is a gift; you can choose to accept it or ignore it as you see fit. Unfortunately, we know that when we hear things about ourselves that we perceive as negative we tend to believe them, and when we hear positive things, we tend to discount them. So, I would like to ask you,

What unhelpful narratives are you currently telling yourself?

Addressing these can be really helpful when making a career switch (and indeed even before). Identifying such narratives can be tricky, especially if they have become deeply ingrained. Therefore, therapy and/or a good coach can help you to develop such self awareness.

Additionally, for me, there are a few things that have helped me lean into the unknown and let go:

• The importance of play – according to Stuart Brown, as humans we are designed to play; to test, experiment and do things without purpose, just to see what happens, or because they feel good. I have always used play to offset the stress of the corporate world and it’s no different during time of transition. Play looks different for all of us. For me, leaning into play means allowing myself to be more authentic and free, by not taking everything so seriously and by being openly silly. By reducing the seriousness of the ‘big’ decisions, it can take away the pressure to make the ‘right’ decision just as the sailing approach allows.

• The importance of curiosity – a good friend of mine and former colleague, Clare Inkster specialises in this topic and inspires me to embrace curiosity on every occasion. I love curiosity because it gives permission to explore, to not have the answers, and also forms the foundation of every strong relationship.

• Get out of your own way – try to identify what you may be doing that is holding you back. Ask yourself what you are not allowing in, by trying to control things. This can be hard to acknowledge and scary to let go, but simply having an awareness of this can already be a useful first step.

• ‘Yes, if’ – this is my favourite tip and one I have used ever since I learned it on an executive leadership course many years ago. Change your ‘no, because’ into ‘yes, if’. So, to give you an example of this in action, when deciding whether to make the move from corporate to startup your, “….no, because I will lose my big salary” becomes “yes, if I can earn x / yes, if I can supplement my income / rely on my savings” or “no, because I don’t know how to do x” becomes “yes, if I can learn how to do x / hire someone to do x” etc. The ‘yes, if’ is always hiding in the ‘no, because’, you just have to play with it.

• Growth mindset – according to Carol Dweck, our most basic abilities can be developed through dedication and hard work — brains and talent are just the starting point. I find this helpful because it creates freedom and opportunity to grow. With this viewpoint, nothing is permanent and therefore change or failure need not be feared. There is one single word that I like to use with myself, and my coaching clients, and that word is ‘yet’. Such a tiny word with so much power. Try adding it to any sentence where you are telling yourself what you can’t do and/or haven’t done. Simply by adding the word ‘yet’ for example, “I haven’t attracted x clients…yet” or “I haven’t mastered y skill…yet”, completely changes the meaning of the sentence; you move from a definitive no, to a possible yes.

Get ready to jump

To conclude, it’s important to remember that only you know what is right for you. And, by the way, you do know. You just have to listen.

Commit and believe in yourself.

Hold on and enjoy the ride.

As I write this, I have no idea where I’ll end up, but I’m proud I tried something. I hope you too can find a nugget in here to help you follow your own dreams.

Best of luck and thanks for reading.

If you’re interested in starting personalised coaching to get more of what you want in life and work, please reach out to katie@re-humanise.com.