Newsletter #19

Beyond winning: Finding your way to Authentic Success

Hi there

I was at a networking event last week when I bumped into someone I hadn't seen in probably ten or twelve years. Let’s call him Steven. It was one of those moments when you're genuinely pleased to see someone you hadn’t expected to see. He looked great. He was clearly doing well for himself. And we spent the first part of our conversation catching up on the usual things.

His business had grown. He'd won industry awards. From the outside, he seemed that to be enjoying a successful life. He seemed to have cracked the success code.

Earlier in the evening I’d been invited to say a few words to everyone to help promote my book. As part of the talk I shared some of my own struggles and the journey I've been on over the past few years.

As we spoke, Steven explained that he didn’t have a clue about what I’d been through. He then opened up a bit more about the truth behind his own success… "I’m not sure how to keep going on like this. It doesn’t come easy to me at all."

Here was someone who had built everything he'd set out to build. Who looked successful, and was successful by every usual measure. But he was talking to me about the weight of continuing that success and whether the cost was worth it. Which led me to a more interesting question…. “If this type of success doesn’t feel successful, what does?"

It struck me that this incredibly successful person felt in some way trapped by his own success. At first I thought this was unusual but it did occur to me that, as a culture, we've become incredibly good at one half of the success equation; business success. We can optimise, strategise, and execute our way to impressive commercial results. But we’re not so adept at the other half of the equation; life success.

We’re maybe not as clear or knowledgable about finding meaning, contentment, freedom and wholeness. The path to these inner human needs remains largely hidden in uncharted territory.

So, I've been thinking about Steven’s challenge a lot this past week and it strikes me that what might be missing is his ability to cultivate "authentic success". A term I’m coining to capture the integration of external achievement with internal alignment. Business success plus life success.

Because it seems to me that Steven is operating with only half the formula. 

The Expensive Emptiness

I’m pretty sure Steven isn't alone in this struggle. I sense there's a quiet epidemic among successful professionals. People spending years climbing every ladder put in front of them, only to realise that there’s a more important ladder to be climbed; the one they choose for themselves.

I don’t see this as a dramatic midlife crisis. It's something more subtle than that. It’s the growing awareness that we could do our jobs in our sleep. That the problems we're solving don't actually need solving by us any more. That the skills we've spent decades developing could be creating something much more meaningful instead.

It’s a time of life when it feels like your success has plateaued. It’s a time for a change. A shift. A new adventure that creates meaning and puts vibrancy back in our lives.

But we don’t change. We stay stuck. We do what Steven did - continue the struggle and pretend we’re enjoying the success.

Why don’t we change?

Is it because we think it’s too late to try and do ‘another big thing’? Are the risks even bigger precisely because we’ve been so successful in the past? What if we aren’t as successful as before? Have I got it in me? Am I too old?

The Golden Prison That Isn't Actually Locked

Here's where I think it gets interesting.

Many of us don’t make the shift because we assume that we're trapped by financial obligations. The mortgage, the lifestyle, the responsibilities we've accumulated. But somewhere along the way, without really noticing, many of us cross a threshold. A comfortable, life as usual, spending threshold.

We become used to a level of spending without checking whether it’s making us any happier or not. We just spend the money we spend because that’s what we spend. That’s what we’ve always spent.

In 2020 I experienced a sharp fall in my income as the all projects I was working on got cancelled as a result of the pandemic. One by one the recurring invoices disappeared. I panicked for a couple of days. And then I got into radical cost cutting. I managed to reduce my monthly spending by more than half. It took me a few months to get there but I did it.

I suppose it was easier to cut costs in 2020 but I know my current outgoings are still significantly lower than they were in 2019. And the crazy thing is - I couldn’t really tell you what benefit I got from the addition spend. I was spending twice the amount I am now and I don’t know why!

Anyone can go through this process. Have a go yourself. My bet is that you’ll soon realise you could take a significant pay cut and still maintain a great quality of life. You’ll discover you have options you didn't know existed. The worries about making a career shift because of money insecurities will disappear. The golden handcuffs you thought you had on weren't actually locked - you’d just forgotten to check.

But as you do this, I’ll let you into a secret.

I’m not sure lack of money IS the real issue. Protecting your income levels isn’t the real barrier to you embarking on a new, meaningful career path.

I think there is a deeper barrier to a second half of life adventure.

The Permission We Didn't Know We Needed

That deeper barrier is permission. Not external permission - nobody's stopping us from making changes. I’m talking about internal permission. The permission to want something different. To believe we deserve a shot at finding meaningful work. To trust that the skills we’ve honed in the first act of life could translate into impact we care about in the second.

This is imposter syndrome in reverse. We're not worried about being qualified for the work. We're worried about being qualified for our own, unique calling. Who are we to think we could really be called into action? Who am I to make a difference? Don't these roles require passion and experience I don't have?

Here’s my heartfelt belief: if you've been successful once, you’ll be successful again. Even if success starts meaning something completely different.

The Search for Something Real

The challenge isn't finding motivation or passion - that's too simplistic. It's about understanding how your existing skills could create a career and impact you care about. It's about building bridges between who you are and who you're becoming.

This isn't about throwing away everything you've learned. It's about applying it differently. Your strategic thinking, your problem-solving abilities, your understanding of systems and processes - these don't become irrelevant when you start seeking meaning. They become tools for creating the kind of change you actually want to see.

What Authentic Success Looks Like

Authentic success isn't about choosing meaning over money. It's about integration. It's about designing work that honours both your financial responsibilities and your need for purpose. It's strategic, practical, and honest about the complexities.

The question isn't whether you deserve meaningful work - you do. Everyone does. The question is: what would it look like to design your next chapter around the impact you want to create instead of just the income you can generate?

Because you didn't get this good at what you do just to keep doing it forever. You got this good so you'd have the skills, resources, and confidence to do something that matters. Something that matters to you.

The only question is: are you ready to figure out what authentic success looks like for you?

In the next newsletter I’ll be sharing my thoughts on the various dimensions of Authentic Success. And I will include a link to a special assessment so you can find out for yourself.

Until next time,

Simon