Photo taken at Alptitude retreat

Breaking free: A love letter to floundering founders and career changers

And those with an entrepreneurial flame that needs rekindling

Laurence McCahill
The Happy Startup School
5 min readJan 9, 2024


Dear friend,

I’ve heard your stories like yours many times.

About feeling trapped in a golden cage of your own making.

Where your zest for work is no longer there like it once was.

That something is missing, you’re not just sure exactly what.

But you know this feeling.

That your soul is slowing dying.

And there’s an urge to break out that just won’t go away.

One thing is key — you can’t see your future here.

But you’re stuck.

Maybe the money is good, it gives you a sense of security or there’s the carrot of the promised land.

You’re locked in to the needs of your employer or your own clients.

But you know there is more to work and life than this.

Waiting for life to start.
Postponing your happiness.
Hoping tomorrow will be different.

But you have so much more to give. To yourself, to others and to the world.

“Follow the dreams of others and you will receive a paycheck. Follow your own dreams and you will never check your pay.”― Vincent Lowry

It’s time

We don’t have much time. Yet we live as if it is infinite. If we’re lucky we’ll make it to 4000 weeks.

You’ve probably heard of the top 5 regrets of the dying, made famous by pallative care nurse Bronnie Ware.

Here’s a reminder:

  1. “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
  2. “I wish I hadn’t worked so hard.”
  3. “I wish I’d had the courage to express my feelings.”
  4. “I wish I had stayed in touch with my friends.”
  5. “I wish I had let myself be happier”

If you’re like me when I was in a similar situation, 1 and 5 strike deep. Yet happiness takes courage — and often the right question.

Back to Oliver Burkeman:

“If you’re at a fork in the road in your life or career, don’t ask ‘what will make me happy?’, but rather this prompt from Jungian psychotherapist James Hollis:

‘Does the path I’m about to embark on enlarge or diminish me?’

This typically helps us discriminate between the kinds of unpleasant challenges that are a necessary part of growth versus those that are bad for us in the long term.”

And yet change is hard to do on your own.

We get sucked into other people’s worlds and visions.

Which can lead to conflict — not necessarily with others, but with ourselves.

Our choices can lead us to experience tension with our own core values.

Which in turn ripples out to the rest of our lives — our health, wellbeing and relationships can suffer. And eventually, our work too.

But it can happen so slowly that we end up stuck in environments with cultures and reward systems that don’t nourish us.

We sacrifice what’s important in the interests of keeping the peace.

Yet at some point we can’t take it any more.

Doing nothing becomes more painful than moving forward.

We’ll only truly find happiness when we commit to our future selves and say ‘I deserve this’.

A brighter future

I’m writing this to let you know that I’m here, we’re here. To sit next to you. To listen. To support. To challenge. To connect.

And hopefully inspire you — that there is another way.

One where you get to live in tune with your deepest beliefs and values. Where you get excited to go to work every day. And spend your days with people you love and respect, and who respect you back.

Where you can confidently say “this is the work I’m here to do”.

And over time, work out ways to get paid well to do it.

Myself and my business partner Carlos have been living this dream (reality) since we started The Happy Startup School in 2012. Whilst there have been some hard times and real challenges, I’ve never wavered from the mission.

This is the work I’m here to do.

To inspire, empower and connect people that want to live their lives from a place of purpose and connection. To pursue the work that lights them up, to be a lighthouse for others — and in turn make the world a better place.

Photo taken at Happy Startup Summercamp

And our little secret?

When you create space for those that commit to this path, who move forward despite the fear — something magical happens.

  • Clarity and excitement builds
  • Possibilites emerge
  • Friendships develop in no time
  • Collaborations happen effortlessly
  • Ideas serendipitously appear at the right time

“When you act with deep integrity, the universe conspires to support you.” Frederic Laloux

So I would encourage you to listen to that internal voice.

The part of you that knows what to do. What Jamie Catto calls the ‘wise guru in charge of a mental patient’.

Because when you do, you open yourself up to the full spectrum of life 🌈

Where your work just becomes an extension of who you are, not the part you wish away.

With love and compassion,


🚀 If you’d like to be part of an inspiring journey towards a more exciting future for you and your work, Tribe 9 of our Vision 20/20 group coaching program starts in March 2024. Learn more and register your interest at



Laurence McCahill
The Happy Startup School

Designer, coach, entrepreneur. Co-founder The Happy Startup School.