“Commit to the Lord whatever you do and He will establish your plans.” –Proverbs 16:3

Being your own boss seems to be the new American Dream. Everywhere I go, I see “Lady Boss” slapped across anything from sweatshirts to coffee mugs to lipstick cases. My Facebook feed is log-jammed with ads begging me to sign up for a copy-writing course or a life coaching seminar so I can FINALLY earn seven figures by simply writing from my laptop while enjoying my view of the mountains in my favorite cozy pj’s. That easy, huh?

I love what I do. And most days (most!) there is nothing I would rather do than do my own thing. My schedule is flexible, but it takes samurai-like discipline to manage my time.  I have yet to balance my bank account from a pool chaise in a bikini sipping a mojito though I confess I have answered many of your emails while sitting for a potty break.

I painted furniture for friends and family for many years starting when I was about 12 (it’s an interesting story!) and managed a darling a retail shop in Wisconsin for a time where I received a lot of hands-on experience in styling and design. I often considered doing my own thing, but it just never happened. When my last position was terminated in 2018, it was time to free fall into what I had dreamed of for so long. When I plunged into self-employment, I felt like Indiana Jones. Do I skedaddle across the shoddy rope bridge or do I stay and swashbuckle the encroaching savages? I chose to plug my nose and cannonball into the swirling waters below.

As my own boss, I wish I would have known a couple of things ahead of time. Knowing these three things wouldn’t have stopped me from choosing self-employment, but it would have better prepared me for the hard realities of lady boss life.

  1. Being self-employed can be lonely.

I am an extrovert. I like people and I love building relationships with them. In my corporate life, I enjoyed public speaking, group brainstorms, and event planning. Now, I work in my garage and talk to my dogs. For an extrovert, this can be a hard adjustment. I try my best to schedule coffee and one lunch a week with a friend.


  1. You’re going to be broke.

And probably for a while. Although I had a small emergency fund set aside for a scenario such as mine, it didn’t take long before mortgages, groceries, and business needs scarfed that up. It took some time for me to manage business finances and home finances effectively before I started to see a profit turn. You’ll have to tighten your belt when you get started. Sure, selling your first $500 item sounds awesome (and it is) but once you subtract cost of goods, taxes, and your time and effort, there’s not much left. It takes time to turn a profit. It just does.

3. You need a plan.

In my case, I didn’t have time to think. I just jumped. Be it divine timing or otherwise, I didn’t have time to hem and haw and doodle a pretty business structure in my day planner. I just did it and figured it out along the way. As you evolve, your business must do the same. You need a plan. A simple business plan will do and there are people to help you craft it if have no clue where to start. SCORE (Service Core of Retired Executives) is a phenomenal organization and their help is FREE! This is a no-brainer. Knowing where you are and where you want to go and the best route to take is crucial.  It’s like Waze for your business! You can identify roadblocks, hazards, and sticking points long before you get there.

If you decide to pursue your dream of self-employment, do as much research as you can before making the decision. Here’s an article I wrote on taking the plunge.

You can do it!