Becoming Your Own Boss: Give Yourself Permission

Everyone talks about the benefits of being their own boss – working from wherever you want, working on your own schedule, the increase in money, and other things. They also talk about the drawbacks of being your own boss – self employment taxes, healthcare, business taxes, and the ups and downs / peaks and valleys of finding work or clients.

I want to talk today about the day-to-day things you may have forgotten you need to do since you are boss and employee. We usually only ever think of being boss and employee at tax time when we have to pick up both pieces of FICA – employee and employer or certain healthcare expenses. Disclaimer: This is not to be considered tax advice. There are times other than tax time or healthcare time that you need to remember you are boss and employer.

Mental Health Days: As an employee you used to take mental health days, play hooky, get your work done so you could ask permission to leave early, or quietly hope the computer systems would ‘stay down’ so you get to go home. Those are the fun things you have happen randomly as an employee. In some ways you may have felt you were ‘sticking it to the man’. Well now you’re the man. And you need to feel free to still stick it to the man on occasion because no one is going to do it for you.

Special Event Days: Remember how your company used to have a special day at Six Flags, the Zoo, or baseball game? They were employee teambuilding activities or family activities such as the company picnic right? Well you are your own boss so you will need to seek those opportunities either with your family or perhaps with yourself. Take a day and go to the Zoo. Take a day and go to the baseball or hockey game. You are the boss!

Call Your Spouse: During the workday you would call your spouse. You might have even done it at lunch break or gotten yelled at for doing it too often. Well…when you became your own boss you may not have continued to take those little breaks. Take the breaks. Call your spouse. Call your parents. Call your children. You used to do it when you were an employee anyway.

Bonuses: As an employee you used to get a Christmas bonus, performance bonus, or commission. It’s important to set up some pay structure for yourself but if you are a sole proprietor or single member LLC, you need to set up some kind of structure to compensate yourself on occasion beyond the norm so you can stay motivated to stay in the game. If you are a corporation, consult your board of directors / compensation program of course. But for smaller entities, it’s important that you recognize the need to give yourself what you got as an employee.

Employee Wellness Program: Remember when your employer would bring a chair massage person into your office each year? Well now that’s on you. If you want to go for a chair massage, find a place with a chair massage in the middle of the day, the same as you would if you worked in a cubical and left for 30 minutes to go to your health services and get a massage. Do you need to get help with blood pressure, diabetes, or other screenings? Your employer may have done that for you in the past so now you have to feel free to go to CVS, WalMart, Kroger, or another pharmacy provider and do it yourself – during work hours.

Vacations: As an employee, you get a set number of vacation days, in general you are told when you can and cannot take them in accordance with other employees and the needs of the business. You save up all year, count on a bonus, and go. Now that you are your own boss, you need to set that goal yourself, figure out how much business you need to make it work and set up a sinking fund – the dollar amount that vacation costs – and put money aside on a regular basis – so you can take your vacation on cash. There’s nothing like a vacation you don’t keep paying for when you get back. The very function of a vacation is a employer directed benefit – and now you are your own employer so direct that benefit!

Employee Development: In an employer-employee relationship employers are responsible to identify areas of improvement and pay for your training as an employee. You might have looked at these as ‘days away from the office’ where you had fun, networked, and learned things. Well when you are your own boss, you have to seek those opportunities, schedule them, pay for them, and go to them. Some of it may require humbling yourself while others may be related to a gig you want to score. Regardless they are good opportunities for networking, time away, and skill sharpening so you can market yourself more effectively. But no one’s going to tell you to do this like they did when you were an employee.

Go Home, Go Home, Go Home: When you were working for someone else, they would tell you to go home, whether it was seeing you were overworked, the company running short on overtime money, or just plain common sense. When you are your own boss, you tend to work longer hours for yourself than you’d work for someone else. In some cases especially during startup, that is good and a healthy start to the business, but over time it’s critical that you tell yourself to go home. Do so for your spouse, for your children, for your pets, and for yourself.

Don’t forget for a single day that you are your own boss. It’s a wild ride. But don’t be afraid to stick it to the man, knowing you are the man. You didn’t leave one slave driver to become another slave driver.