21 Lessons I Swear By After 21 Years as an Entrepreneur


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I start mine Business, five months after September 11, 2001, was no easy task. There was a lot of uncertainty in the world and no one wanted to spend money. To top it off, I had no clients. I was just armed with a lot of confidence and the Yellow Pages. As an enthusiastic 23-year-old, I started calling 20 companies every day. I worked nights in a call center and sold charity raffle tickets for the first 18 months until I got regular work.

On the 21st anniversary of starting my own business, I’m sharing 21 lessons I’ve learned since starting it over two decades ago. During that time, I ran my advertising agency during the SARS outbreak, the 2008 global financial crisis, Covid-19 and lockdowns.

Here are my 21 lessons I swear by:

1. You can have the best plan, but that doesn’t mean it will work out.

Don’t waste time thinking about every single detail, instead spend that time making your project happen. Oftentimes you can hesitate and make sure you have everything lined up before you begin, and while it’s good to be prepared, you can never plan everything. Progress is often better than perfection.

2. Always get your payment in advance

You’re not a bank and you shouldn’t have to give your customers 30 days to pay. As we know, 30 days often turns into 90 days and often it’s just a single default payment that can have a massive impact on your cash flow.

3. Make time for yourself every day

Whether an hour of sport or just five minutes to take a deep breath and concentrate on your thoughts. If you don’t put on your oxygen mask first, you can’t take care of anyone else.

4. Don’t let the person who isn’t pursuing their dreams stop you from pursuing your own

The easiest thing you will find in the world is someone who will happily give you a whole list of reasons why you cannot achieve your dreams. It’s often best to do what you want to achieve without telling anyone, and then when you’ve achieved your goal, you can shout it out loud. That way, you won’t be discouraged by critics.

Related Topics: How to keep motivated when surrounded by naysayers

5. Set aside your taxes in a separate account every time someone pays you something

This will improve your cash flow when paying your annual tax bill. If you don’t, it could be tempting to spend the money you owe the IRS on a quarterly or yearly basis, and you’ll find yourself in trouble. Too often I hear from people who are really successful in their business but have not taken into account the taxes they have to pay each year and then have to struggle to raise funds.

6. Scale your business internationally

Don’t just bet on settling in your own country. The world is a small place. There are people abroad who want your product or service. If it’s easier, you might even consider franchising your business to make it global and allow you to grow more than you ever thought possible.

Related: 5 Invaluable Lessons for First-Time Entrepreneurs

7. Whatever worked last year, last month, or even yesterday doesn’t mean it will work today

You always have to stay up to date and try new strategies. For example, if you run a digital marketing campaign through social media channels, you may find that the cost per click is higher than ever today as people choose to opt out of being tracked. Instead, you could implement a PR program to help you increase your exposure through earned media.

8. Don’t build a business that relies on just one customer

This is not a business and it gets too stressful when the customer leaves. Instead of spending all your time with one major account, take some time to start acquiring additional customers to diversify your customer base and ultimately take the risk.

9. When conflict arises, take the higher path

Do this by listening and not getting defensive. From dealing with suppliers to customers, it is important that you treat others as you would like to be treated and watch your behavior because ultimately it is a reflection of the business you are trying to build.

10. Make sure you share your story and incorporate it into your corporate communications

Everyone has a great story and customers will be more connected to your business if you share your journey and explain why you decided to start your own business.

11. Find a mentor

There is always someone who paved the way for you to talk to and learn from their mistakes.

12. Educate yourself

There will always be new ways to do things more efficiently. From listening to podcasts that dive deep into a topic you need to know more about, to investing in training programs that will help you improve your business skills, it’s important to keep learning.

13. Systematize your processes

Make sure all your systems are in place and documented so someone else can follow you if you’re ever down.

14. Get everything in writing

From customer agreements to negotiations with suppliers, it’s important to always put your dealings in writing for two reasons. The first is that you are often very busy and you may forget what you promised someone or what they promised you and the second is that you have a file to go back to should problems arise in the future .

15. Live by your school slogan

“Nil Sine Labore” was my high school motto, which means “nothing without hard work” in Latin, and I think about it every day.

16. Control how you react and it will transform your business

You cannot control what is happening in the world around you, but you can control the way you react to external events. As an entrepreneur, there are always ups and downs, and you must learn to ride the waves that come your way.

17. Love what you do

If you don’t enjoy it, then quit and change your career. Life is too short.

18. Give something back

Be it through donations, volunteer work, or volunteering with a charity. It is rewarding and will bring more meaning to your life.

19. Business cards are not superfluous

It’s the best form of remarketing. Someone who pulls out their jacket at the next wedding, holiday party or meeting may find your card and think of you a few months later.

20. Be consistent

Whatever your marketing, sales or growth strategy, you need to be consistent with it. For example, if you’re trying to attract more customers by posting on LinkedIn, you can’t post three times a week and then not post for a month. You have to be consistent.

21. You don’t always need an investor to get your business idea off the ground

Don’t worry about finding an investor to support you in realizing your idea. Be supportive and above all, believe in yourself. If you don’t support yourself, no one else will either.

These 21 lessons above have helped me start my business, stay in business and eventually grow my business internationally. Just because you’ve been in the game for many years doesn’t mean it will get any easier, but rest assured that following these strategies will help you master the path ahead. Enjoy the ride.

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