20 Lessons from 20 Years in Business: The Ups, Downs, and Everything In Between
Author: Annie Page
January 22, 2025
It was the 4th October 2004 and my first day as self employed – leaving behind over 15 years of being employed.
It’s been an interesting journey with incredible highs and some serious lows, and some very boring parts in between and filled with more lessons than I could count. But I’ve decided that I can count some of them and here are 20 key lessons that have shaped who I am today and how I run my business. From surviving the 2008 financial crisis to navigating the rapid pace of change, here are the lessons I’ve learned that may resonate with anyone who’s ever had to rebuild, pivot, or simply keep going.
1. Adapt or Get Left Behind
Business never stays the same. Over the years, I’ve learned that the ability to adapt is critical. If you can’t change with the times, you’ll quickly find yourself obsolete.
2. Resilience is Everything
Losing 75% of my business in 2008 was a tough blow, but it taught me that resilience is more than just surviving – it’s about growing and thriving even when the odds are stacked against you.
3. Mindset Matters
Your mindset is everything. The ability to approach challenges with a growth mindset, rather than a fixed one, has been instrumental in navigating the ups and downs.
4. People Matter More than Anything
Your relationships – with clients, employees, and partners – are at the heart of everything. I’ve learned that treating people well, and building trust, will take you further than any quick win ever could.
5. Cash Flow is King
Profit margins are great, but without solid cash flow, you won’t last long. Understanding the difference and managing cash flow has been key to weathering tough times.
6. Delegation is Hard (But Necessary)
Like many business owners, I struggled with delegation. Learning to trust others with important tasks has been vital to scaling my business and keeping my sanity intact.
7. Get Comfortable with Discomfort
Uncertainty is the norm, not the exception. Being in business for 20 years has taught me that you have to learn to operate – and even thrive – in discomfort.
8. Technology Changes Everything
From automation to digital marketing, technology has transformed the way we do business. Staying on top of these changes has been key to staying relevant.
9. Continuous Learning is a Must
What worked 10 years ago doesn’t work today. Continuous learning – whether it’s new strategies, tools, or business models – has been crucial to staying ahead.
10. Your Network is Your Net Worth
The people you surround yourself with matter. Over the years, I’ve found that a strong network can provide advice, opportunities, and support when you need it most.
11. Embrace Change
The ability to embrace change has been one of the most important factors in my success (so important I did the research and wrote a book about it ‘Thrive through Transition’!)
12. You Can’t Please Everyone
In the early years, I tried to be everything to everyone. Big mistake. You can’t please everyone, and trying to do so is a fast track to burnout.
13. Trust Your Instinct
Data is important, but your instincts matter too. Some of my best decisions came from trusting my instinct, even when the numbers didn’t back me up.
14. Failure is Part of Success
I’ve failed – more than once. But I’ve come to understand that failure isn’t the opposite of success, it’s part of the journey. It’s where the biggest lessons come from.
15. Self-Care is Non-Negotiable
You can’t pour from an empty cup. I’ve learned that taking care of myself – physically and mentally – is essential if I want to show up as my best self in business.
16. Success is a Marathon, Not a Sprint
There’s no such thing as overnight success. My journey has taken 20 years of persistence, learning, and adapting. Success takes time.
17. Marketing is More Important Than You Think
When I started, I thought a great product or service would speak for itself. It doesn’t. The right marketing is essential to getting your message in front of the right people.
18. Accountability Drives Results
Accountability – to yourself and others – is key to achieving results. Holding myself,my team, my clients accountable has been what’s made the biggest difference in reaching our goals.
19. Celebrate the Small Wins
Not every day is filled with big wins. But I’ve learned to celebrate the small victories along the way – they’re what keep you motivated during the tougher times.
20. Gratitude is Powerful
Last but not least, gratitude. I’m grateful for the lessons, the setbacks, the people, and the successes. It’s easy to get caught up with everything and forget to step back, but taking the time to appreciate the journey is what makes it all worthwhile.
20 years in business has been full of highs, lows, and everything in between. I’ve had to rebuild, pivot, and adapt more times than I can count, but every challenge has brought valuable lessons (although some I had to learn more than once!)
What’s one lesson that has defined your business journey? I’d love to hear about it!