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  • Joan Wilkening

12 Things I wish I'd known when I started my 1st business

Updated: Jun 11, 2018

As a serial entrepreneur, I’ve started quite a few businesses, some large (several retail stores) and some small (vegetable stand, grass cutting, babysitting) but there was always a common theme: I wanted to make money. We learned as kids we could earn money doing stuff around the house or for neighbors. This was in addition to our weekly allowance. Woohoo, in those days an extra $2.00 was a big deal to a kid!


I’ll never forget the day I asked for a raise from the family I’d been babysitting for. I watched their two kids several Saturdays a month while they had date night. I asked for a $0.25/hr raise. They never called me again. I was shocked, hurt, and confused. I figured if they can afford to go out, they can afford to pay me a bit more. It would only equate to an additional $2.00 per Saturday. But, to them I guess it was too much, they started using someone cheaper. What lesson did I learn? That someone else controlled when I worked and how much money I made.


My Dad owned his own business. We saw first hand the long hours he put in, the struggles he had with staff, and the vacations me missed because he was always working. I remember being surprised when he opted not to expand, I couldn’t understand why he didn’t want to get bigger, have more, do more, make more. But, he had a plan and it didn’t include working more hours!

My Dad working on a model back in the day

Those of us who have built a business worry about every detail and hope we’ve planned for every possible situation. Somehow, we always miss something or are surprised by a turn of events. Here’s a few things I wish I’d known:


1. Not everyone is going to like you. That’s a tough one because it’s human nature to want to be liked and accepted. Either because of fear of competition or a personality conflict, not everyone will welcome you with open arms. Accept it. It’s okay. Stand tall. Take a deep breath and continue.

2. Practice. Every day will not go as planned. You didn’t learn your craft over night, it will take time to figure it all out. And guess what? After you figure it out, it will change. It will always change.


3. Set boundaries in all areas of your business. No, Aunt Suzy does not get a discount and cousin Fred cannot use your equipment. Your biggest struggle will be establishing yourself as a business person. The sooner you do this the better, it’s a business, treat it like a business.


4. Realize your strengths and get help with your weaknesses. Sounds obvious right? There are many aspects of running a business - figure out what you’re good at and then get help with what you’re not good at, like bookkeeping, cleaning, human resources, etc.


5. Progress is progress no matter how small. Each day presents new opportunities, a do-over if you will. As you grow your business, you will become more confident and secure, even baby steps are moving forward. Don’t get impatient - slow and steady wins the race.


6. Invest in yourself by taking classes, attending workshops and conferences. In spite of what you may think, you don’t know it all.


7. Write a business plan. There are many free templates available. Find one that works for your industry and use it. I know, we don’t like the “work stuff”, the planning stuff, but you really need to have a plan.


8. Websites and social media are an absolute must. No discussion.


9. Get it in writing. From everyone. Handshakes are good after you sign the agreement, not instead of the agreement. As friendly as things are now, next month might be different... no, next month will be different. Even if they say it’s not necessary, jot it down, even a confirmation email can work as an agreement. Remember, it works both ways, don’t be insulted when “they” ask you to sign something.


10. Money is important when planning a business and running a business. It always costs more than you think and you never have it when you need it. But, it isn’t everything. Plan for it, use it, save it, give it. We tend to use it as the barometer for success. Instead, look at your happiness. Does your business make you happy?


11. It isn’t as difficult as it looks. Don’t over-plan and under-deliver (otherwise known as procrastination). Some of us are really good at the planning, but not so good at the executing because we want everything to be perfect. It’s never going to be perfect. Jump in. You can do it.


12. Take a vacation. Rest, don’t quit. No one expects or needs you to work 24/7 and if you do, you’ll burn out. This is the biggest struggle I have, I don’t take time for myself. I feel guilty if I’m not working all the time because people depend on me to run the business. Train the team, trust the team, and take some time for yourself!


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Norfolk, VA

Joan Wilkening, Founder

Mrs. Pinkadot, Retail Store

Design Your Business, Web-based Coaching 

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