Why We Keep Solving the Same Problems… and Secretly Love It

Problems

Spent some time at a London-based network for business owners and senior operators. It was good to be in a room with peers again — people who get it. The kind of people who know that sales and marketing challenges never quite vanish. That operational systems are always “just one tweak” away from working flawlessly. And that people issues… well, they’re part of the fun, aren’t they?

Something tells me we all enjoy this strange ritual: gathering to share war stories, compare scars, and call it “learning.” The truth? It is learning. But it’s also a form of collective therapy for founders, leaders, and doers who refuse to sit still.

The Persistent Trio: Sales, Systems, and People

Some challenges in business are like recurring characters in a long-running TV show — familiar, occasionally infuriating, but you’d miss them if they were gone.

  • Sales & Marketing: The growth engine that’s never “finished” and always needs a tune-up.
  • Operations & Systems: The invisible scaffolding that keeps everything standing — until a crack appears and you have to rebuild a section overnight.
  • People: The heart and the wildcard. Their brilliance drives success; their quirks keep you on your toes.

We might lose sleep at night, but solving these problems is what keeps us sharp and adaptive.

The Books That Supported the Conversations

Three recommendations stood out — each tackling a different dimension of the leadership puzzle:

  1. Boundaries: How to Draw the Line in Your Head and Heart — A reminder that not all demands on your time deserve a “yes,” and that sustainable leadership starts with self-preservation. The reason we discussed it is the danger of being a ‘rescuer’ (read the book) and a business leader simultaneously, dangerous for all parties.
  2. Managing the Professional Service Firm by David H. Maister — The definitive guide for anyone leading a knowledge-based business. Maister blends strategy, people management, and client relationships into a roadmap for long-term profitability.
  3. Gut by Giulia Enders — Proof that leadership stamina isn’t just mental; it’s biological. Enders’ fascinating dive into the gut’s role in health shows how this “second brain” influences everything from mood to decision-making resilience. We all know the price we pay when we don’t trust our gut.

The Real Lesson

No business challenge ever truly disappears — it just changes form. Mastering leadership isn’t about achieving a mythical “problem-free” state, but about building the stamina (and humour) to keep dancing with the same themes, at ever-higher levels of complexity.

I was humbled, having met a founder of a government-funded charity who was effectively being squeezed by ALL sides and still managed to smile.

So yes, maybe we do enjoy this “punishment disguised as learning.” And maybe, just maybe, that’s what makes us better at what we do.

Links for the curious:

Picture of Hutton Henry
Hutton Henry
Hutton has worked with Private Equity Portfolio firms and Private Equity funds since 2015.Having previously worked in post-merger integration for large firms such as Ford and HP, Hutton understands the value of finding issues prior to M&A deals.He is currently the founder of Beyond M&A and provides technology due diligence for VC, PE and corporate investors, so they understand their technology risks before entering into a deal.

Take our FREE Scorecard to find out if your investment is at risk.

Discover the value of technology in your portfolio and target investments to gain more confidence and uncover potentially significant risks that could affect the value of a sale or an acquisition.

More Stories