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21 Lessons I Swear By After 21 Years as an Entrepreneur

21 Lessons I Swear By After 21 Years as an Entrepreneur


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Starting my business, five months after September 11, 2001, was no easy feat. 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 self-belief and the Yellow Pages. I’d start each day cold calling 20 companies a day, as an enthusiastic 23-year-old. At night I’d work in a call center, selling charity raffle tickets for the first 18 months until I had regular work coming in.

Celebrating 21 years since starting my own business, I share 21 lessons I have learned since diving in and launching over two decades ago. During this time, I have operated my publicity agency through the SARS outbreak, the global financial crisis in 2008, Covid-19 and lockdowns.

Here are my 21 lessons that I swear by:

1. You can have the best plan in place, but it doesn’t mean it will happen this way.

Don’t spend time overthinking every single detail, rather spend that time on the implementation of your project. Often you can procrastinate, making sure to have all your ducks in a row before you start, and while it is great to be prepared, you can’t ever plan for everything. Progress is often better than perfection.

2. Always get your payment upfront

You are not a bank and shouldn’t have to provide customers with a 30-day due date for payments. As we know, 30 days often turn into 90 days and it often is just one default payment that can have a massive impact on your cash flow.

3. Take time out for yourself every day

Whether it’s one hour of exercise or just five minutes to breathe and focus on your thoughts. If you don’t put your oxygen mask on first then you can’t look after anyone else.

4. Don’t let the person who doesn’t chase their dreams stop you from chasing your own

The easiest thing you’ll find on Earth is someone who is happy to tell you a whole list of reasons why you can’t achieve your dreams. Often it’s best to go about what you want to accomplish without telling anyone and then once you have reached that goal you can shout it from the rooftops. By doing so you won’t be discouraged by naysayers.

Related: How to Maintain Motivation When Surrounded by Naysayers

5. Put aside your tax in a separate account each time someone pays you

This will help with your cash flow when it comes to paying your annual tax bill. If you don’t it may be tempting to spend the money that you owe the tax office each quarter or year and you’ll find yourself in trouble. Too often I hear of people who are really successful in their businesses but haven’t accounted for the tax that they will need to pay each year and then have to scramble to find the funds.

6. Scale your business internationally

Don’t set your sights on just establishing yourself in your own country. The world is a small place. There are people abroad that will want your product or service. If easier, you could even think about franchising your business to help make it go global and allow you to grow more than you ever thought possible.

Related: 5 Priceless Lessons For First-Time Entrepreneurs

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

You always have to stay on top of trends and try new strategies. For example, if you are running a digital marketing campaign using social media channels, you may find that the cost per click is higher now than ever before as people are selecting to opt out of being tracked. Instead, you could implement a PR program that will help you boost your awareness with earned media.

8. Don’t build a business that is reliant on just one client

That’s not a business and it will become too stressful when that client leaves. Instead of spending all of your time on one major client, ensure to take some time out of your day to start securing additional clients to diversify your client base and ultimately risk.

9. When conflict arises, take the higher road

Do this by listening and not being defensive. From dealing with suppliers to clients, it’s important that you treat others the way you want to be treated and be mindful of how you conduct yourself as ultimately it’s a reflection of your business that you are trying to build.

10. Ensure that you share your story and make it part of your corporate communications

Everyone has a great story and customers will resonate with your business more by you sharing your journey and why you decided to create your own company.

11. Find a mentor

There is always someone else who has paved the way for you that you can speak with and learn from their mistakes.

12. Keep educating yourself

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

13. Systemize your processes

Make sure you have all your systems in place and documented for someone else to follow if you’re ever out of action.

14. Put everything in writing

From client agreements to negotiations with suppliers, it’s important that you always have your deals in writing for two reasons. The first is that you’ll often be really busy and may forget what you promised someone or what they promised you and the second is that you have a record that you can refer to should there be any issues in the future.

15. Live by your school slogan

Nil Sine Labore was my high school motto which is Latin for “nothing without hard work” and it’s something that I reflect on daily.

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

You can’t control what’s happening around you in the world, but you can control the way you react to external events. There are always ups and downs as a business owner and you have to learn how to ride these waves that come your way.

17. Love what you do

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

18. Give back

Whether it’s through donating, doing pro bono work or volunteering at a charity. It’s rewarding and will add more meaning to your life.

19. Business cards aren’t redundant

It’s the best form of remarketing. Someone, when pulling out their jacket at the next wedding they go to, or Christmas party or meeting, will find your card, possibly several months later and will think of you.

20. Be consistent

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

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

Don’t worry about finding an investor to back you to get your idea off the ground. Back yourself and most importantly believe in yourself. If you don’t back yourself, then no one else will.

Theese 21 lessons above have been instrumental in me launching my business, staying in business and ultimately growing my business internationally. Just because you have been in the game for many years doesn’t mean that it will get easier, but you can be sure that following these strategies will help you navigate the path that lies ahead. Enjoy the ride.

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