A Hero’s Journey

James Gairdner
4 min readJul 17, 2020

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Starting and building a business is hard. Like the innocent hero in the fairy tale, founders may begin with an uplifting vision but seldom realise quite how challenging the path ahead will be. Faced with significant personal and professional risks which require relentless physical and emotional dedication, the experience can provoke extreme highs and all consuming lows. This can have a profound impact on the personality and health of those who choose it.

However, it is only once a vision finally becomes reality that the real challenges begin. Making it past the start up phase, is usually just a ‘false summit’.

Once a business has achieved scale-up, the challenge becomes preparation for and moving towards the next phase, transition to a scalable, sustainable enterprise, when a company can begin to ‘come of age’. The company will need new disciplines, structures and systems and often a very different mindset. It will need new investors, new relationships and new governance, and with every significant capital injection comes new expectations.

The optimism of the early years gives way to “an ugly adolescent period” with intimacy replaced by an increasing disconnection; the entrepreneurial spirit with a sense of suffocation; the agility with a slower and more lumbering pace. Like adolescence, this period may often appear messy and uncomfortable, accompanied by feelings of resentment and a desire to return to the ‘way it used to be’. Crucially, businesses risk losing sight of what they are trying to achieve and kill the energy and belief upon which they were founded.

Already exhausted by previous trials, our hero begins to recognise the need for fundamental change but is often unclear how they might make this transition or even whether they have the energy to try.

Like adolescence, it can be important simply to recognise that this is a normal part of the growth cycle. If we are to take the advice of Winnicote, all that maybe required is the patience to allow it to take it’s course. However, this is perhaps cold comfort for high growth businesses where progress is measured in days and weeks, not months and years.

That said it is also important to recognise that this transition requires more than funding or more blood, sweat and tears. It is also perhaps important to acknowledge it may not be the business that needs to change but the founders themselves.

At this juncture is may be helpful for founders, leaders and employees to seek a guide for the journey, who can provide some perspective and make sense of the dynamics they are experiencing. This guide may begin to help them understand what changes this transition will demand of them, whilst at the same time reshaping the psychological contracts and relationships that define their organisation.

In doing this it maybe helpful to get a fresh perspective beyond the more rational frames of traditional consulting and business advisory services to consider what may lie ‘below the surface’. In service of understanding the underlying causes of the business’ challenges, with a view to making better choices about what to do next.

To be successful, any transition needs to acknowledge the inner journeys’ of both the founders and the people in their organisations. Both are coming to terms with a new reality and considering what the future looks like, and may have mixed views about what they see. For this reason it is often helpful to work along two parrellel paths.

On the one path founders need to consider who they are and what their hopes and fears are for the business they have built and, on the second, for the leadership group to consider who they are and what they are in the process of becoming. Both must individually consider what the business will demand of them and frankly whether they have the will and the skill to meet it’s needs.

It is then important for both to come together and consider the implications of this for their relationships and the culture of the business as a whole. In doing so they must reflect on their own habits and behaviours and understand how these may have contributed to the organisation they have built, and then engage in conversations that will help redefine how they will work together and the respective roles they will play to secure the future of the business.

For many founders this can be a challenging time. This may feel like Odysseus return to Ithaca, who on finishing his journey, discovered that the home he had left was not the same, that his family no longer recognised him and he had to rediscover his place. In the same way founders must redefine their place, in a business they have built, but is changing and can never return to how ‘it used to be’. They must recognise the leaders they need to be to move the business forwards.

It is only then perhaps that the organisation can move forward with a renewed sense of energy and purpose.

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