How entrepreneurs can escape isolation, rediscover connection and lead well

Jamal had ridden the euphoric rollercoaster of building a rapidly scaling business. The incredible
growth that he and his team had achieved not only brought momentum and recognition, but also
the exhilarating sense that almost anything was possible. Then the business reached its next stage of development. Yes, it was still growing, but the rate was slowing causing feelings of doubt and anxiety to creep in. “Don’t worry, you’re still doing great.” Jamal’s chair of the board advised.
Despite this reassurance, Jamal’s anxiety didn’t abate. Instead he started withdrawing. Conversations became harder and he spent less time with people who knew him beyond the
business. What was worse is that all the noise of his internal doubt drowned out the clear thinking and considered thought that helped him be successful in the first place. Not knowing what to do, Jama’s behaviour became erratic. Sometimes he was distant and disengaged. At other times, he overshared, spilling worries into conversations without considering what others needed from him. Things came to a head during an interview, when he let slip that he felt lost and out of control. What he had struggled to acknowledge privately had surfaced publicly, which made a great headline for the journalist. Following the disastrous interview, I was recommended to Jamal by a mutual connection. “Rob will help you reground yourself and get back to being your best,” was how it was positioned to him. Our work began with the person carrying the strategy.

Step off the pedestal
Entrepreneurs are often put on pedestals. We celebrate their vision, applaud their conviction and
expect them to keep producing miracles. For some that attention can be intoxicating, where at the extreme, founders can start believing their own hype and a run of success begins to feel like proof of invincibility. But the pedestal is a precarious place to lead from. It can pull entrepreneurs away from the humble, focused leadership their business needs. When this happens listening gives way to performing. Curiosity shrinks and asking for help starts to feel like letting the audience down and allowing the cracks they are hiding to appear. And from the position of the pedestal, when performance falters and growth slows the founder faces more than a commercial challenge – their identity is under threat.

The dilemma of isolation
Whilst there will always be many factors influencing the mindset and performance of an
entrepreneur, one dilemma which so often becomes amplified during moments of stress is the human dilemma of Isolation. How? Because in the moment when they are most vulnerable, they are confronted by the fact that none of us can hand over responsibility for our own life. Nobody else can fully inhabit our experience or remove the need to choose, where entrepreneurship intensifies that reality because so many other people depend on our decisions. Amid all his challenges Jamal was fighting his isolation. And as he became increasingly lonely, he felt
the tension of wanting certainty from others whilst feeling compelled to manufacture it for them.
Accepting responsibility meant recognising that some decisions were his to make, where better
connections could help him make them well. With this recognition we focused on three practices to help him refocus and deliver.

Anchor back to your best self
We started by exploring who Jamal was when he was at his best. This meant looking beyond the
celebrated founder to the person whose judgement, values and behaviour had helped build the
business. The questions we considered were: Think about a time when you led well. What did you stand for? How did you listen? How did you respond when challenged? What would people have experienced in your presence? Jamal used his answers to define behaviours he can return to under pressure: asking before assuming, listening before defending, explaining decisions clearly and acknowledging what you do not yet know. The result was that Jamal stopped measuring himself solely through business growth and reconnected with how he wanted to lead through it. In this context, understanding and reconnecting with who you are when at your best is not simply
remembering who you are, it is a deliberate practice of being that person in every conversation.

Build a network that supports and challenges you
A founder can have hundreds of contacts and nobody they feel able to call honestly. Build your support around what you actually need. A coach can create space for reflection. Other
founders can offer shared experience. A mentor can challenge your judgement. Friends and family
can reconnect you with life beyond the business. It is important to recognise that no single relationship can carry all of that. Therefore, choose people who will question you as well as reassure you. An echo chamber of admiration can keep you on the pedestal, and an echo chamber of anxiety can keep you trapped in fear. Jamal also needed to distinguish honest leadership from uncontained disclosure. He recognised that his team deserved candour about the challenges facing the business, whilst also needing direction. For Jamal, developing a network of trusted support gave him somewhere to work through his uncertainty before deciding how to communicate it. He then sought to ensure these relationships were not ad hoc encounters, but were part of his diary.

Create space to reconnect
When pressure rises, reflection is often the first thing entrepreneurs sacrifice. Every spare minute gets swallowed by another meeting, message or attempt to force progress. Whilst it felt uncomfortable, we made space a deliberate practice for Jamal: protected time to step away, reflect and reconnect with himself. During this time we then focused on three questions: Who am I? Why am I here? How will I live? Although simple on the surface, these questions helped him reconnect with his identity, purpose and intention. They helped him go beyond the tactical and day-to-day issues to strengthen his foundations for leading, living and performing.

What you do next matters
We can all get knocked off course. Success can inflate us. Pressure can disconnect us. Responsibility can feel overwhelming. The key is what we do about it. Standing on the pedestal of entrepreneurship can feel seductive, especially when accompanied by admiration. But existing from this place can also result in isolation which draws us further away from who we are as our best selves. Overcoming the potentially debilitating impact of isolation requires you to accept the decisions that are yours to make, seek people who help you see clearly and keep returning to who you are and how you want to lead. It is only through these practices that as an entrepreneur you can not only continue to prosper, but you can also continually strengthen the foundations of identity, purpose and practice for how you lead and live.