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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 task. There was a lot of uncertainty in the world and nobody wanted to spend money. To top it off, he had no customers. I was armed with a lot of confidence in myself and the Yellow Pages. I would start each day cold calling 20 companies a day, like an enthusiastic 23 year old. At night he worked in a call center, selling charity raffle tickets for the first 18 months until he had a regular job.

Celebrating 21 years since I started my own business, I’m sharing 21 lessons I’ve learned since diving in and launching it more than two decades ago. During this time, I operated 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 may have the best plan, but that doesn’t mean it will happen this way.

do not waste your time overthinking every detail, rather spend that time implementing your project. Often you can procrastinate, making sure you have all the ducks in a row before you start, and while it’s good to be prepared, you can never plan everything out. Progress is often better than perfection.

2. Always get paid in advance

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

3. Take time for yourself every day

either one Excercise time or just five minutes to breathe and focus 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 doesn’t pursue their dreams stop you from pursuing yours.

The easiest thing on Earth you’ll find is someone happy to tell you a whole list of reasons why. you can’t achieve your dreams. It’s often better to do what you want to achieve without telling anyone and then once you’ve achieved that goal, you can shout it from the rooftops. In doing so, you will not be discouraged by detractors.

Related: How to stay motivated when you’re surrounded by detractors

5. Put your taxes in a separate account every 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 can be tempting to spend the money you owe the tax office every quarter or year and find yourself in trouble. Too often I hear of people who are very successful in their businesses but haven’t accounted for the taxes they will have to pay each year and then have to scramble to find the funds.

6. Scale your business internationally

Don’t set your sights on simply settling in your own country. The world is a small place. There are people abroad who will want your product or service. If it were easier, you could even think of franchising your business to help you go global and grow bigger than you ever thought possible.

Related: 5 invaluable lessons for first-time entrepreneurs

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

You always have to be aware of trends and try New strategies. For example, if you’re running a digital marketing campaign using social media channels, your cost per click may be higher now than ever as people opt out of being tracked. Instead, you could implement a public relations program that helps you increase your awareness with earned media.

8. Do not build a business that depends on a single client

That’s not business and it’s going to get too stressful when that customer leaves. Instead of spending all your time on one lead client, make sure you take time out of your day to start securing additional clients for diversify your customer base and ultimately risk.

9. When conflict arises, take the high road

Do this by listening and not getting defensive. From dealing with suppliers to customers, it is important that you treat others as you want to be treated and that you are aware of how you behave, since ultimately it is a reflection of your business What are you trying to build?

10. Be sure to share your story and make it part of your corporate communications

Everyone has a great story, and customers will resonate more with your business if you share your journey and why you decided to start your own company.

11. Find a mentor

There is always someone else who has paved the way for you who you can talk to 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 delve into a topic you need to know more about to investing in training programs that will help you improve your trading skill set, it’s important keep learning.

13. Systematize 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 customer agreements to supplier negotiations, it’s important that you always have your deals in writing For two reasons. The first is that you will often be very busy and may forget what you promised someone or what you were promised and the second is that you have a record that you can refer to in case any problems arise in the future.

15. Live by your school slogan

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

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

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

17. Love what you do

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

18. Returns

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

19. Business cards are not redundant

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

20. Be consistent

Whatever your marketing, sales or growth strategy, you must be consistent with it. For example, if you’re 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 up to get your idea off the ground. Support yourself and most importantly believe in yourself. If you don’t support yourself, no one else will.

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


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