5 Regrets That Every Business Leader Should Learn NOW

Introduction: Pause. Reflect. Reset.

In the fast-paced world of business and business ownership, it’s easy to get swept up in the grind—client deadlines, staffing pressures, cash flow, compliance, and a growing to-do list that never seems to end. 

You’ve achieved what many only dream of—clients, cash flow, a growing reputation. But at what cost?

In business, burnout hides behind big numbers. Isolation hides behind influence. And far too often, “success” becomes a slow and silent killer—of health, joy, relationships, and peace of mind.

The real irony? You may be building a life that looks successful on paper while slowly losing the things that matter most - YOU and perhaps your family.

There’s a story I heard that’s stuck with me ever since. It wasn’t about spreadsheets, profits, or strategic growth. It was about a man and the silent cost of relentless ambition.

He built an empire.
But lost everything else.
The family.
The health.
The wonder.

At 78, he sat across from a colleague of mine—tired, successful, alone.
“I don’t know,” he said quietly.
“I climbed the ladder.
But I never stopped to ask where it was taking me.”

That one sentence should stop us in our tracks.

Because I’ve heard versions of this more than once. From founders, partners, CFOs, and directors. Leaders who gave everything to their work… until they had nothing left of themselves.

It’s a silent sacrifice that too many are making:

• The boardroom wins, but the home is cold.
  
  
• The investors are impressed, but your kids barely know you.
  
  
• The numbers soar, but your joy flatlines.
  
  

“For what shall it profit a man, if he shall gain the whole world, and lose his own soul?” (Mark 8:36)

That verse isn’t just scripture. It's a strategy. It’s wisdom. It’s your alarm clock.

So here’s your invitation today: Stop. Pause. Reflect. Let this title not just grab your attention—let it be your invitation to make one simple change.

Because these five regrets don’t just belong to the dying.

They belong to the living—to help us choose a different path before it is too late to do so.

Why? Because Regret Has a Pattern

Bronnie Ware, an Australian palliative nurse, spent years with people in their final days. She captured their five most common regrets in her book, The Top Five Regrets of the Dying. 

These aren’t just reflections of a life gone by—they’re warnings for those of us still on the treadmill, especially in high-performance, high-pressure roles like yours.

Let’s walk through those regrets—reframed for business owners, accountants, and leaders like you—and find the one simple change you can make today.Make sure it is something that you repeat at say 2 monthly intervals so that if it is a small step, you keep the momentum up!

Regret 1: “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

How much of your business is built on what you think others expect? The pressure to conform—to industry norms, client demands, or the idealised image of “success”—can pull you far from your values.
Tip: Revisit your vision and values. Write them down. Ask yourself: Is my business aligned with what is really important to me; who I really am and what I truly want? If not, adjust one thing. One client. One boundary. One yes or no.

Regret 2: “I wish I hadn’t worked so hard.”

Busy professionals often wear overwork as a badge of honour. But many do not wish they’d spent more time at work and less time at dinner with their family.

Tip: Plan your next busy season now. What can be automated, delegated, or done in advance? Book a half day off next week and don’t move it. Protect it like your most important meeting—because it is.

Regret 3: “I wish I’d had the courage to express my feelings.”

Many leaders hide behind professionalism, leaving their true nature at the door. But honesty builds trust—within teams and with clients.

Tip: Open up. Share a real thought in your next team meeting. Ask a colleague how they’re really doing. Tell a client what you appreciate about them. These moments build loyalty and lift morale.

Regret 4: “I wish I had stayed in touch with my friends.”

The lonely leader is a common theme. The further up the ladder you climb, the fewer people you talk to that aren’t billing you—or being billed by you. True friends knew you before you were at the top of the ladder and will likely keep you grounded.

Tip: Call a friend. Not a business contact. Not a mentor. A friend. Book a coffee, send a text, write a card. Personal relationships are foundational. Don’t let your calendar betray your values.

Regret 5: “I wish that I had let myself be happier.”

Success doesn’t require sacrifice of joy. In fact, joy is a sign you’re building the right thing. Many (myself included) are so busy doing the doing, that we forget ourselves in the process. Allowing time and space to do the things that you love and do them more and more, is very important ON your journey through life.

Tip: Do something today purely because it makes you happy. Not productive. Not profitable. Just joyful. Then ask: Why don’t I do this more often?

A Final Thought: Success Shouldn’t Hurt

You don’t need to lose everything to realise what matters. You don’t need to wait until 78 to ask where your ladder is leaning.

• You’re allowed to build a thriving practice and have dinner with your kids.
• You’re allowed to impress clients and take a long weekend.
• You’re allowed to lead with strength and make space for stillness.

Make one change today.

Because your firm’s legacy won’t just be built on numbers.

It will be built on who you became in the process—

And who you brought along with you.

Let this be your pause, your reminder, Your invitation to reflect… and choose better.

Kim Searle is a dynamic Mindset Coach dedicated to helping individuals achieve emotional calm and mental balance. Passionate about personal growth, she empowers clients to overcome stress and anxiety, unlocking their full potential for greater calm, clarity and confidence..

Since COVID-19, awareness around well-being has grown, yet many remain unsure of its impact. Kim demystifies this by highlighting how our inner self shapes success and resilience. She believes habits, thoughts, and emotions hold hidden keys to growth and fulfilment.

With experience in major organisations like NatWest, Motorola, and Vodafone, Kim understands modern pressures—constant juggling, workplace dynamics, and personal demands. After facing burnout and Glandular Fever in 2017, she founded Emotional Mastery Ltd to guide others on their journey to self-discovery.

Her mission: to help clients reconnect with themselves

Be More You