Are You Your Own Boss?

Have you recently become your own boss? If Yes – what have you learned from the experience?

A year ago I was consuming any information I could find on becoming my own boss, but focusing strictly on what kind of legal entity I would be and how I would pay for health insurance. Since then I have learned a few lessons that were not covered in the stuff I read; I now take keyboard in hand to share them with you and ask you to share with us what you have learned.

Being my own boss - Year 1.

Reflecting on being my own boss – Year 1.


Don’t tell your friends and family you are retiring to start a new business. The only part they heard was “…retiring…,” so they think you are now a person of leisure just looking for opportunities to keep busy. Instead, tell them you are leaving your old employer and taking a new job (if that’s the case). Then establish and stick to a schedule, and train friends and family on when it’s OK to call and chat.


Discuss with spouse, children and anyone else living with you what it means to work from home. I could write an entire book on this topic. If you have never worked from home before, even when an employer may have given you that opportunity, you should try it before you make it permanent to become aware of the pitfalls you may encounter. Whoever lives in your house – train them to leave you alone when you are working. In a small house this can mean keeping the television, kids and pets turned down low if you need quiet to conduct business. And if that doesn’t work, check out life hack expert Joel Falconer’s (@jfalconer) ideas for making the office to home transition.


Be careful not to overcommit to volunteer opportunities. If your new start-up business allows for it, volunteering when you first leave your job seems like a great way to keep busy and make new contacts. Caution – it’s also a great excuse to procrastinate, avoiding that part of starting a new business you find most difficult. If you have the time to volunteer, seek opportunities in your industry where you can find brains to pick while at the same time giving back to the community.


Pick the right tool kit. Coming from corporate life I never realized how many decisions were made for me –and I took for granted. From which health insurance to purchase, to how my computer would be backed up, someone else took care of those things, usually after a lot of research and maybe trial-and-error. Accept that you might make some bad choices along the way, so look for opportunities to try before you buy. Subscribe to the shortest period possible (note-free trials rarely give you the functionality you need and often are not good tests of a product), get opinions from other businesses in your industry. Check with your local Small Business Administration ( or if in the Jacksonville, FL area, the Small Business Development Center at UNF for information about products and services geared specifically for you, the small business owner. Don’t be afraid to walk away if a product or service isn’t working for you.
Exercise your networking skills as you never have in the past. If your role in the corporate world was internal-facing, this is a critical step in launching your business. Maybe friends and family don’t purchase what you are selling, so ask if they know anyone who does and if they will introduce you. Seek out events that your buyers attend and get used to walking up to strangers and starting a conversation – not a sales pitch. Call up former co-workers to find out what they are up to and if they can help you or refer you – after all, they know your work. You know people who want to help you succeed – you just have to find them.


What about you – what “Aha” moments have you had running your new business? What best advice would you like to share?


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