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AllwoodJennifer Allwood HomeBusiness Trainingworking mom

So you think you want to be self-employed?

By January 13, 20143 Comments


I know you see me sitting by the neighborhood pool in the summertime in the middle of the day.  And I know what you may be thinking…..”it sure must be nice to be self-employed”.  Or maybe “it must be nice to have other people out working for you while you relax”.

LOL.  Grace, grace, grace to you my friend.  I used to think those things too.  Until I became self-employed almost 14 years ago.

It’s been on my heart to write a blog post about self employment for a while.  Not in an attempt to pound on my chest and puff my self-employment status up.

It’s also not an attempt to martyr myself and try to make anyone feel sorry for us business owning peeps.

Rather, it’s to educate.  And to encourage the people out there who are standing with one foot in both the employed world and in the self-employed world…..and who are trying to decide in which direction to head?

It’s to encourage the young momma who wonders if she has what it takes to start her own business?

And to some degree….it’s to defend us business owners who have paid our dues, who have worked our butts off  when no one else was looking and who know the behind the scenes struggles of self employment.

Here is just a little of my personal story:

I was laid off from my desk job at Birch Telecom as a soft developer 14 years ago.  I had no aspirations of being self-employed.  I didn’t know the first thing about it.  I thought the majority of America worked for someone else because well….it’s just what you did. You got up.  You went to work.  You got paid every other Friday.

Insert my big company going thru a downsizing.

Insert me being CRUSHED that I was let go in the layoffs.

Insert but I had been faux painting for a few people on the weekends.  This “extra money” would get us by until I found another desk job….

Insert God totally knew what He was doing.

Insert “The Magic Brush” began.

Here is what I didn’t like about corporate America.  I had to wear what they required.  I had to be there when they wanted.  I had to worry about my future employment being in their hands.  I had to stay at my desk the required 8-10 hours even when I spent half of my day googling “faux finishes” or “painting company”.  Let’s just say this….if I were still at a desk job today, I can’t even imagine the hours I would spend on Facebook, Instagram, Twitter and Pinterest. And sadly, it would be on the company’s dime….because when I was done with my work, I always had to stay until quitting time and I was bored stiff.

I hated

Thank God for the people who enjoy that.  My hats are off to them.  But I just was not one of them. I would have suffocated had I continued down that path.  I am so grateful God shook up my world when He did.

And so I became self-employed kind of my accident.  I had no idea what I was doing.  I just asked people smarter than I.  Mentors, other business owners, painting instructors. I basically learned as I went.

And here is what I have found about self employment.  There really are 3 levels to it. They are as follows:

1) being self-employed for “extra money” or making a little money “here and there” to help out.  The selling of your trade or good is not required for the family to operate.  The stress level is relatively low in this level of self employment.  Usually your “job” is still very enjoyable and you can do as much of it as you feel like or don’t feel like.  It’s very low pressure.

2) The family counts on you bringing in an income.  In other words, you have to sell your skill or product because the income you generate is needed.  The pressure level goes up.  You must learn “the hustle”.  You have to become business minded.  Your family is depending on you, therefore a shift occurs.

3) Now you are self employed/a business owner AND you have people working for/with you.  The entire ball game changes.  Think taxes.  And insurance.  And people issues.  And not only YOUR mortgage depending on you making money….but others are depending on you to make money also. You now must manage, direct, plan, market, sell and find your way in the business world.

So, in my business….  I thought I would stay at level #1 until I could find another “desk job”.  But then I saw that wow….I have a skill here.  And people are willing to pay for that skill.  And hey, this is super fun.

And so for a year, it was just me at the Magic Brush.

Then I got pregnant, had a baby, got pregnant, had a baby, got pregnant and had another baby. So in that mix, I hired my sister-in-law 12 years ago and she still paints for me today (she is unbelievably talented and I am unbelievably blessed). A few years later, I hired several more people.  And, today I have 8 girls painting for me and am getting ready to hire an administrative assistant.

Let me just say this….when you begin to have employees/staff/contractors working for you…..EVERYTHING changes.

Now you must know insurance, rules, regulations, laws and a million other things you don’t have any desire to understand….or you will be billed.  Or sued.  Or in trouble.  Now, you must be BUSINESS MINDED.

Now you must arrange your schedule and the schedules of all the people who work for you.  So, you gotta be ORGANIZED.

Now you must be a leader and your team will need you to be confident, able to make quick decisions, and to make discerning decisions for the betterment of the company. Because now, people are depending on you.  You must work even when you don’t feel like it because if you don’t work… they aren’t able to work.  And not only are your bills on the line, but so are theirs. You must be DEPENDABLE.

You will only keep good  people working for you if you are good to work for.  And a high turnover rate is NOT a sign of a good employer.  This means you need to appreciate your people.  You need to show integrity on the job.  You need to feel your way through drama and delicate employee situations and character issues.  Now you must be an EXPERT OF PEOPLE.

You must be a SELF STARTER. There is no one getting you out of bed in the morning and since you aren’t “clocking in” or reporting to an office….there will always be a temptation to slack.  But this is the self employment truth: if you don’t work; you don’t eat.  It’s as simple as that!

You must be able to navigate social media or you will be left behind.  You must be a MARKETER.

You must be good a good TIME MANAGER or you will experience burn out and work non stop.

You must be good a good MONEY MANAGER or you will inquire business debt, not be able to make payroll or not charge enough for your skill/product.

You must be a good DELEGATOR because few people can do their trade and all of the above.

And ….you must be humble enough to ask for help in any of the above areas that you are not skilled in.


And so back to the original example of me by the pool during the summer.  One of the reasons I love being self-employed is because it allows me flexibility to be very present as wife/mom.  Self employment allows me blessings like:

  • never missing a kiddo’s field trip
  • always being able to be home with them when they are sick
  • I am able to take as much vacation as I want and when I want

But I pay the price for those advantages as I sit by the pool, because as I sit there, I am texting my girls who are out working on my behalf.

I am checking bank accounts to be sure I can make payroll on Friday.

I am calling builders to be sure that the house we painted for them last month will be getting paid to us this month.

I am ordering supplies.

I am scheduling in my mind.

I am thinking of what I need to load in my truck for supplies that night when I get home.

I am thinking about how quarterly taxes need to be filed.

And oh, have I updated Facebook today?

And why didn’t I bring thank you notes to the pool to write to clients?

I am sitting by the pool with my kids…. but everything in me will want to  mentally check out…. because I am thinking about work.  I am working when I should be concentrating on those precious babies.  Oh yes, I nod my head in the appropriate spots,  I get into the pool on occasion, I chat with girl friends.  But it’s very,verrrrrry hard to turn work off.  And any business owner will understand what I am talking about.  It is a constant battle I have.  Balance is so hard. Please tell me I am not alone here????

And so there are times when I look longingly at my friends who have 9-5 jobs and I think it would be nice to have.  Nice to “turn it off” when you clock out. Nice to have vacations where you actually get to relax the whole time and never think about work.  Nice to know what your income will be from one week to the next.

And then I look back at my life and I see all the blessings on this side too. How I will be blogging at midnight tonight but it’s ok because I don’t have to get up early for work tomorrow.

And how I will be selling another DIY video tonight as I am sleeping.  How cool is it to make money while I’m not “at work”?

And I will stomp my feet at my tax bill next week, but I will thoroughly enjoy being at my kid’s field trip to the zoo next month.

I was bummed that on Christmas night I had to start planning for our work day for the next day. But I was so excited when I learned that the month of December was my most profitable month of the year this year.

So see, there are pros and cons in every job whether self-employed or employed by someone else.  And thank God not everyone wants to be self-employed.  I am so thankful for the people who work retail, manufacturing, teachers, doctors, police officers, accountants etc.  Wouldn’t the world be wacky if we all attempted self employment??

So, whether or not self-employment is a good fit for you boils down to your personality, your lifestyle and your natural bends or God-given talents. And it also depends on which of the levels of self employment you are interested in? So, if you think you want to be self-employed,

  • Are you self disciplined?
  • Are you a self-starter?
  • Are you able to handle immense amounts of pressure?
  • Are you good at establishing boundaries?
  • Are you good at leading?
  • Are you good enough with people that they will want to be led?
  • Do you have a spouse or family on board with your plans?
  • Are you comfortable asking for money?
  • Do you believe in your product/skill enough that you are willing to charge enough for it?
  • Are you able to admit failure and try again?
  • Are you comfortable trying new things and being out of your comfort zone most of the time?
  • Are you able to manage money in the fat months in order to prepare for the lean months?
  • Are you good at your craft in addition to social media, advertising, accounting, etc?
  • Do you understand that you MUST delegate things you aren’t good at?

Yes, yes and yes?

Then go for it. I completely encourage self employment.  Whenever I meet someone who is self employed, I instantly have a level of respect for them. because I know where they have walked and I know what they have sacrificed and I know what they go thru.

So, I am rooting for you!

Take the plunge.

Jump on in.

The self-employment pool water is just fine.


Many blessings,






  • Hi Jennifer, I have been self employed for over twenty five years. It hasn’t always been easy, but so worth it. This is a great list to consider for someone interested in becoming self employed.

  • Hello Jennifer,

    This blog was fantistic and you nailed it perfectly. I am the lady that called yesterday about my home decor shop in St. Joe Mo. I diffently think everyone thinks it’s easy and has so many perks… But they have no idea that there are ALOT of give and take in being self employed! You also forgot to mention that must of your time being spent working you don’t get paid!! I feel very blessed to have a talent that people need and would be willing to pay me for… AND I LOVE GOING TO WORK:)
    Thanks for sharing!
    Tabitha Yount

  • Jesse says:

    I really enjoyed this post! Thank you so much. I would love to be self employed, and the fear is there but I definitely feel I could handle it. The thing that scares me most, taxes… paperwork… insurance.. payroll. But if it has been done then I can do it too, right? Thank you so much for this encouraging post 🙂

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