Ideas About Self Employment

self employment ideasSelf employment is a dream for me because I can choose when and how much I want to work. It also has it’s downsides as well. Here are my ideas on self employment.

Retirement Contributions

Con-Even though I have been essentially self employed for years, I had someone who kept up with deposits, bills, payroll deductions and taxes,  book work and issued a paycheck to me twice a month. I could set up how much to contribute to retirement and not really have to think about it other than to rebalance from time to time.

Now, I have a solo 401k, and I am solely responsible for funding it. Yes, I can set up recurring contributions, but the money still goes into my account before I can send it on. It is sometimes really hard to pull the trigger and let that money go. It’s much easier when it comes out of your paycheck and you never see it. I also don’t get any company match.

Pro– The overwhelmingly positive thing about having a solo 401k is that I can not only contribute the full $17,500 employee contribution, I can also put in 25% of the net profits from my business up to $51,000. While I’d love to make enough income to contribute that full amount, I’m not there on 3 days a week. I should still be able to sock away $30,000 this year if I can stick to my plan of putting all of my optometry income in the 401k.  Having multiple steams of income allows me to do this, so I can’t say enough how important it is to diversify.

I can also contribute pre-tax to our health savings account for another $6550 of tax free money.

Taxes suck for self employed people because you don’t have an employer contribution for half of your Medicare and Social Security. With being able to put so much in tax deferred accounts, it more than makes up for any company match or plan. You just have to be disciplined about sticking to your contribution schedule.

With self employment, you also have to be responsible for making sure your business is properly insured and that things like unemployment and worker’s compensation are filed correctly. Not taking care of these issues can result in interest and penalties.

Time Off

Con– Although, I rarely took off work, if I did I still got paid. I even was able to keep taking a full paycheck during my 6 months of maternity leave, which was a good thing as we didn’t have much of an emergency fund back then!

Now, if I don’t work, I don’t get paid. I have some really awesome employers at the moment who will let me make up days or sometimes switch them around if I need to, but if I took 6 weeks off, I would not have a paycheck.

Pro– I have been able to structure my schedule so that I average about 3 days a week in the office, which is perfect. I get to put on my professional clothes and be Dr. Kim for a few days and then still be able to do on 1st grade field trips. I could never have done that working full time and running a practice.


I admit it was a bit weird in the beginning to show up for work and just be an employee when I used to run the show, but now that I’m used to it, it’s great. I can come home most days and just turn it all off.

Before, the business was with me 24/7, and it was extremely stressful. I’ll aways be thinking and making some sort of plan for the future,  but my level of happy is turned up past 11.* I actually had a long time patient who told me how much more relaxed I seemed from when she was in a few years ago. Even when you try to hide it, being stressed out all the time is usually obvious and is a terrible way to live. There is always the chance that one of my contracts could end, but they seem pretty stable for the time being, so that certainly helps lower stress.


I haven’t had one day of regret since selling my practice and working solely on my own. If you want to try self employment, I would suggest having a large emergency fund and making sure you will be able to make up for all the pros of your old job, including the salary. While there were great things about my old job situation, I am 100% sure I made the right decision.

Are you considering self employment? What things do you miss about your old job?

* Bonus points if you know which movie that reference is from.


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Written By
Sydney White is a Texas-born stay at home mom who enjoys spending time with her family, bargain hunting and, of course, writing. She is currently the editor-in-chief of


  1. I’m glad self-employment is working out so great for you, Kim. It would be definitely be an adjustment to go from giving orders to taking them, especially when they may be different orders than I would have given. 🙂 I do know when I went back into private practice, I loved the freedom to schedule appointments around school activities.

  2. As an employee, I loved not being the boss and just coming in to do my job, then home without worrying about it. But being self employed is fantastic for the freedom. Taxes killed me at first (in France as a self employed you have mandatory contribution to healthcare and unemployment without being able to enjoy unemployment if you shut your business down, you just pay for other people) but now I have optimized like you seem to be doing so no complains.

  3. Congrats on being self employed. Don’t pay yourself too much, give your self a modest salary and then dividends. It will save taxes. Do some business travel too.

  4. Can you show up and not be the boss? Do you cringe when you see decisions being made that aren’t the same ones that you would make? Has it been easy to just let all the managing go?

  5. I’m currently considering going back to work full-time, so I’m writing all I can on the bad stuff of work (micromanagers, lack of freedom) to make sure I’m not kicking myself in the face!

    Biggest thing I miss is the camaraderie.

  6. I feel like I’m doing the opposite of what everyone else is doing in that Im looking for full time work. The stress was too much as a freelancer. I’m so glad you’re loving it though and you are a lot happier and more relaxed!

  7. I knew self employment would never be 100% all good, but it sure does sound better than the crap we have to deal with on a daily basis with demanding bosses and customers.

    Bonus question = Spinal Tap the Movie!

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