It was the spring of 2007. Business was booming and I had two attractive offers on the table to sell my business, Fantasy League.
As exciting as this was, I was isolated and ill-equipped to make such a massive decision.
I was enjoying the status quo and an exit wasn’t on my radar. We were about to post our best ever profits and I appreciated the independence of running my own business.
On the other hand, the offers were generous and tempting. One was from a newly established French digital publisher and the other was from a group of South Africans who were bringing a few sports businesses together into a new group.
So, I had the comfort and continuity of the business and life I’d enjoyed for 16 years versus a choice between two opportunities that were lucrative and exciting, but ultimately meant a step into the unknown.
It would have been hard to get objective advice from any of my leadership team as they had their own conflicts of interest around career development, bonuses and share options.
I didn’t have a trusted business network to turn to and didn’t manage to have a proper conversation with any of my friends. So, I was taking this huge decision on my own.
After some soul searching, I finally chose to go for the deal with the South Africans. When I’d visited the French, it felt a little corporate, whereas the South Africans offered a looser structure where I could maintain more autonomy.
Whilst the South African deal promised more, it was a not yet a business, and over the next few months it failed to materialise.
With the wisdom of hindsight, I can see that this choice perfectly reflected my ambivalence.
I wasn’t really ready to sell. I told myself the business would keep on growing. I was happier to stay in my comfort zone and scared of change and the unknown.
I didn’t have the support to make such a massive decision. What I needed was some objective, unbiased advice to open my eyes to some of the personal and business issues I wasn’t able to see.
Someone to help me see that although it may have felt like we still had room to grow, nothing lasts forever and selling as you’re peaking represents perfect timing. (As it turned out we never exceeded that year’s profits).
Someone to explain that working in a larger organisation might actually offer more freedom and resources to create than I’d ever had before.
Someone to remind me what I was being offered equated to an attractive ongoing salary for more years than I could have achieved with Fantasy League PLUS the chance to start a new chapter with new ventures ahead of me.
But I didn’t have someone to help me see all the reasons why the French offer made good business sense, and very good personal sense.
I made the best of my decision - as we always need to do - and have enjoyed a different path continuing at the helm of Fantasy League until last year. It has brought me to where I am today, working as an executive coach where perhaps now I can be that someone for Founders and CEOs.
These pivotal decisions are deeply personal and hit the core of who we are and where we are at a precise moment in time. Being able to talk to someone who’s faced a similar, life-changing decision is the closest you can get to having foresight.
Selling the business might be the biggest decision you have as a CEO, but you’re having to make tough calls all the time.
Does any of this resonate with you? How strong is your support network? How much of it is within the business and how much is separate? Are there conflicts of interest?
Leadership teams and boards are the right forum for many decisions you face as a CEO, but there are others which need to be tackled elsewhere.
Decisions that have a much deeper personal implication –posing important questions around your motivation, ambition, purpose, energy or family – are the ones that require a very different type of support.
Close friends are a great starting point, but if they haven’t run their own business or aren’t prepared to deep-dive into your psyche with you, it may be asking too much.
Sometimes it’s better to speak to someone who is a little removed from your life, with whom there isn’t a personal relationship or any baggage.
Coaching can offer this, provided the chemistry is right. It might be helpful if the coach can share relatable experience, but it’s crucial that they’re not leading you in any way.
Another solution is to join or create your own mastermind group. These are close-knit groups made up of peers working in similar roles who meet regularly over an extended period. The combined energy and wisdom within a group means it can offer an effective space to tackle these significant decisions.
As leaders, over time we grow broad shoulders and by necessity, have to become self-sufficient in many ways.
But there are many times when we need to be able to pause, take stock and think properly alongside others. To recognise that a support system is not a luxury, but a necessity.
Remember, these decisions will always be lonely, but they should never be taken alone.
Andrew Wainstein introduced fantasy football to the UK in the 1990’s, founding and leading Fantasy League through seismic changes in the media and technology landscape. He is now sharing the experience from his journey as a coach for founders and CEOs. He has also launched a new venture called Campfire which is about creating slower conversations to get to what’s important in our work and our lives. https://campfire.cc/about-andrew