There is a part of entrepreneurship that we have become very good at talking about. Failure. I feel we have learnt to romanticise it. We celebrate businesses that failed before they succeeded, founders who lost everything before rebuilding, and the courage it takes to keep going. Failure has almost become a badge of honour, a chapter that every entrepreneurial story is expected to include. Of course, the stories are motivational, of course they come with lessons for all of us and of course success tastes the sweetest when the struggles behind it are copious.
But there is another emotion that seems to find its way in my thoughts and conversations these days. It is the emotion of helplessness. Hear me out! I am not talking about the helplessness that comes from making poor decisions or taking unnecessary risks. I am talking about the kind that sneaks in even when you have done everything you know how to do.
Here is what it looks like. It is spending days putting together a proposal that reflects your best thinking, only for it to disappear into silence of the client! It is having long, meaningful conversations with a prospective client who tells you how much they love your approach, how urgently they need your support and how excited they are to work together… and then hearing nothing for weeks.
It is beginning an engagement because someone assures you that the contract is merely a formality, trusting that the paperwork will follow because relationships are built on trust. The workshops go well, participants are engaged, feedback is encouraging and everyone leaves happy. Weeks later, you are still waiting for the signed contract (because it is important to you!). Months later, you are still following up on payments for work that was delivered with complete sincerity and commitment.
No one really prepared me for this part when I embarked on this path in 2019. When I imagined entrepreneurship, I did imagine freedom, innovation and bold decisions. In reality, so much of it is simply waiting patiently. Waiting for someone to reply to your email. Waiting for approvals. Waiting for contracts. Waiting for payments. Waiting for conversations that felt so promising to become something real. And suddenly with all the waiting and follow up, I have experienced another emotion sneak in – doubt! Was my proposal good enough? Should I have priced it differently? Should I have followed up again? Am I building something people truly need, or have I simply become too attached to an idea?
And what surprises me the most today is how emotionally invested we become in possibilities. Every enquiry arrives as a simple email or query, but within minutes it has already become a future in our minds. We imagine the workshop, the conversations, the people we might meet, the impact the engagement could have. We begin rearranging calendars and scribbling ideas into notebooks before the work has even been confirmed.
When the opportunity disappears, it is not the business that we lose, we lose a future we had already started imagining. So, should we stop imagining? I do not think I can possibly do that and ideas, thankfully, have never been my problem.
My notebooks are full of half-formed programmes, coaching journeys, learning experiences, articles waiting to be written and books that continue to grow one page at a time. Every few weeks I become convinced I have discovered something new for Brewathought. But let me say this – Execution, however, has always been more complicated.
Not because I do not want to do the work, but because life has never politely stayed out of the way. There have been seasons when family needed more of me than my business did. There have been days when health demanded attention before ambition. Moments when the emotional weight of life left very little room for creativity. And yet, businesses should never pause simply because their founders need to.
Clients still expect thoughtful responses. Programmes still need to be designed. Invoices still need to be raised. Content still needs to be written. The brand still needs to remain visible. And having gone through the phase of slowing down multiple times, I have realised that businesses are rarely built on extraordinary days. They are built on ordinary ones.
Like the days, when you write a post even though you are convinced nobody is reading it. When you send one more proposal after the previous three received no response. When you continue refining your work even though nobody outside your own team would notice the difference. Consistency sounds inspiring until you are the one expected to practise it.
A friend who has built a successful consulting practice once shared something that has stayed with me ever since. He told me that before agreeing to work with a client, he spends time listening. Not to the business requirement, but to the person behind it. He wants to understand their story. Why does this project matter to them? What are they hoping will be different because of this engagement? How invested are they in making it work?
At first, I thought he was simply being selective. Today, I understand that he was being wise.
The quality of an engagement has very little to do with the proposal itself and almost everything to do with the relationship that surrounds it. The best work happens when both sides care equally deeply about the outcome. It was one of the times that I started to assess the way I think about clients. I realised it is not just saying “yes” but also about saying “yes” to the right ones.
Perhaps that is another thing entrepreneurship teaches you. Discernment. Over the years, I have been reassessing my own definition of success. In the beginning, I wanted more clients. Today, I want deeper relationships. I would much rather work with organisations that return year after year because they trust us than constantly chase new conversations. There is something deeply satisfying about becoming someone’s first call when they need a coach, a facilitator or a thinking partner. Those relationships allow us to build context together, challenge each other honestly and create work that extends far beyond a single assignment.
And when this thought has been building in my mind, it gets solidified when every once in a while, something remarkable happens on the days I need it most. Like an email arrives from someone I coached years ago. They tell me they finally accepted the leadership role they once believed they were not ready for. Or that a difficult conversation we had stayed with them and helped them make a decision months later. Sometimes the message simply begins with, “I thought of you today…”
A participant from a workshop writes to tell me that something discussed during a session became the starting point for a change within their team.
Someone I have never met sends a LinkedIn connection request saying they have been following Brewathought for a few months and wanted to tell me that they appreciate the way we think about learning and leadership.
None of those messages bring in revenue. They do not clear overdue invoices. They most certainly do not convert pending proposals into signed contracts.
From a business perspective, they change very little and yet they change everything. They remind me that meaningful work has a life of its own. A coaching conversation does not necessarily end when the engagement ends. A workshop does not finish when everyone leaves the room. Sometimes the real impact reveals itself months or even years later, in moments we are fortunate enough to hear about but were never present to witness.
I have often thought that businesses survive on revenue and founders survive on meaning. That revenue alone keeps the organisation alive. Looking back now, I do not think that is completely true.
Entrepreneurship has not made me fearless. If anything, it has made me more aware of my own doubts, my tendency to overthink and my habit of carrying the weight of every opportunity that does not materialise. So much so that at times I joke in my conversations, do not ask me about my rate of conversions because my rate of rejections are much higher than that!
And that has given me clarity. Clarity about the work I want to do, about the clients I want to partner with, about the values I no longer wish to negotiate simply because the market tells me I should.
There was a time when I believed every opportunity deserved to be pursued. Today, I know that saying no is sometimes the most important business decision we make. Not every client is meant for us. Not every engagement aligns with the business we are trying to build. Not every opportunity deserves our energy.
That clarity has come from years of stumbling. From chasing work that was not right. From ignoring my instincts. From believing that growth meant saying yes to everything.
Slowly, I have started letting go of what no longer serves the purpose I have for Brewathought. Not because those opportunities lack value, but because they do not belong in the future I want to create.
Recently, while watching a Forbes interview with Chris Gardner, I heard him say something that felt less like new advice and more like a confirmation of what I had slowly been learning. He spoke about never compromising on excellence, about being exquisite in what you do. If others cannot rise to your level, that does not mean you lower your own.
For years I believed resilience meant adapting to everything. Today, I think resilience also means protecting your standards. It means refusing to dilute your work simply because doing so might make it easier to win business. It means believing that thoughtful work, genuine relationships and excellence still matter, even when the world often seems to reward speed over substance.
So yes, entrepreneurship still has days that feel heavy. I suspect it always will.
The uncertainty, the waiting, the delayed contracts and payment have not disappeared and they are no longer the whole story. The story now also includes repeat clients who trust us enough to come back. Coachees who remember a conversation years after it took place. Participants who write simply to say that something shifted because of a programme we designed.
A business that feels more aligned with who I am than it ever has before.
I have learnt, stumbled and changed and may continue to change. And perhaps that is the real gift entrepreneurship has given me. The confidence that comes from knowing what I stand for, what I want to build and, equally importantly, what I am willing to walk away from.
Every morning I still open my laptop without knowing what the day will bring.
There may be another proposal waiting to be written, another invoice waiting to be followed up on or another opportunity that quietly slips away.
There may also be an unexpected email from someone whose life intersected with mine years ago, reminding me that meaningful work has a way of finding its way back.
And somehow, after all these years, that possibility is enough to make me begin again.