Five Lessons from five years in business

Five years means different things to different people - and species! For dogs, it’s a long time, for humans, it marks the start of your school years, and for business, it means defeating the trend which sees most small businesses fail within their first two years. 

So indulge me while I reflect on my own first five years in business. I started Chuckle Communications out of necessity and curiosity. I needed flexibility for my family after we moved to a new place, and I had pretty modest ambitions. 

But it’s been an amazing ride of personal development, new relationships and a huge learning curve. Here are five lessons from my first five years in business. 

1. Find your people

When I started, I was nervous about losing the camaraderie of an office environment. I thought working for myself would be isolating. But I was wrong. 

Building a network of supportive peers has been invaluable. Whether through online communities, industry groups, or serendipitous collaborations, finding your tribe can transform your business and personal life. Your people will cheer you on, share advice, and even refer opportunities your way. 

Remember, the right people see you as an ally, not a competitor.

2. Progress over perfection

Perfectionism can be a sneaky form of procrastination. 

When I started, I agonised over building the perfect website and branding. But the truth is, your business doesn’t need to be any kind of ‘perfect’ to succeed, it just needs to be functional. Focus on showing up and serving your clients well. 

As you gain clarity and confidence, the refinements will come naturally.

3. No is a full sentence

Learning to say no has been a game-changer. 

Not every opportunity is a good fit, and that’s okay. Saying no to the wrong clients or projects creates space for the right ones to come your way. If something feels off or doesn’t align with your expertise or values, trust your instincts. 

Declining politely and professionally is an act of self-respect and ultimately the kinder move for both of you.

4. Know your worth

When I reflect on my early pricing, I cringe. 

Undervaluing your services can undermine your confidence and attract the wrong clientele. 

You’re not just charging for hours worked, you’re charging for the expertise, creativity, and value you bring. Embrace rates that reflect your experience and skills, and don’t shy away from standing by them.

5. Embrace learning

Running your own business is a constant education, not just in your business and industry, but in yourself. 

Over the past five years, I’ve gained new skills, become more curious, and developed a deeper understanding of my values. Business is never ‘done’. It evolves, as you do. 

And this, my friend, is part of the fun. 

Five years ago, I never imagined I’d be here, reflecting on such a fulfilling chapter of my life. Your business journey will surprise you in the best ways if you remain open to growth and opportunity. Be patient and trust that the right timing will reveal itself.

If you’re at the start of your entrepreneurial path - or somewhere along the way - I hope these lessons resonate. 

Here’s to forging your own path, one lesson at a time.

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