Self-employed me = terrible boss?

Many of my real-life friends are strongly encouraging me to maintain my part-time/remote status with benefits job and use this opportunity to truly recreate myself as an entrepreneur. After all, I already have two steady, paying clients that have other work and projects to fill extra hours. I have made contact with another potential contract job (the law firm Wednesday and continuing with lunch today) that could potentially become a full-time job or an ongoing contract position. If that does not work out, I could market and possibly (probably) attract additional work, because apparently a lot of small businesses out there could use my particular brand of expertise.

The idea has merit and is already modestly successful, so not a terrifying start-from-scratch startup that will consume mass quantities of cash, time, and energy to get going. I have worked as a part-time contractor to supplement my income for many years, have a complete computer and printer and phone system set-up at home, all commonly used software, and a couple of common accounting programs. My personal network of business contacts is a-buzz right now and being hugely supportive with referrals, advice, ideas, and encouragement. I owe a big debt of thanks to many, many people during this weird time.

My biggest concern is health insurance. Of course, I have it if I stay on the payroll with my existing firm as long as possible, and even if that ends I can continue our coverage for up to 18 months, which gives me plenty of time to shop and contemplate what we need. So is that a valid concern or an excuse to not think outside the box and imagine myself succeeding on my own (as so bluntly voiced by a couple of very close friends)? Maybe both.

I think the worst of myself. I think I am disorganized, lazy, undisciplined. Probably I am, at least some of the time. However, when I am on the clock and getting paid to do a job, it gets done and nearly always receives my best efforts and is done well. My part-time job #1 is a well-respected local attorney with a thriving solo practice by choice, and I am his accounting department. I have been doing his books for 16 years, and believe me, if I were not providing good service he would have fired me. My other part-time client is a very successful and affluent businessman who initially hired me to sort out the mess of his personal financial financial life. I did so well with that we have continued our contract, and for him I am a personal assistant and CFO.

For this law firm I could be their office move coordinator and accouting system upgrade transitioner. If and when they are ready to impose retirement on their existing accountant I could potentially move into that role, maybe as a paid employee or perhaps as a contractor. I have another referral to another firm that has finally grown and needs help with their books. This without even trying or working my network of career and business contacts all that hard.

Fear can be a powerful motivator. It’s what keeps me from doing a lot of things that otherwise might tempt me. It can also be something that restrains us from taking calculated risks. Working for someone else seems safe and mostly predictable. It also prevents failure from being 100% my fault.

Would I be happier self-employed? I have always thought no, that I enjoy the interaction and socialization of being with people too much to endure the isolation of being at home and working alone. While this remote office thing is brand new, I see a lot of possibilities in it that never appeared so clearly before. Of course, I have gone to the gym or to yoga practice or out for interviews or all of the above every day this week. I have gotten plenty of social time with other people from these avenues. In truth I speak/text/email with my existing clients several times a week, sometimes several times a day. If I were to go solo into my own business I would slowly acquire more clients and be plenty busy and interactive with them.

So in the interest of being fair to myself, I will give this option serious consideration. On my to-do list for Monday is to make some calls about insurance and licensing to actually formalize myself as a business at my home. In the meantime I may get a great opportunity with another firm – I have already been invited for a second interview with the quasi-governmental association from Wednesday and have a first in-person interview on Monday, a phone interview on Tuesday, and now this second interview on Thursday. In between it is the first week of a new month, always a busy time at all my existing jobs.

I will worry about my disorganized, lazy, undisciplined tendencies later. I could possibly add procrastination to that list as well.

Happy Friday everyone! I am off to my lunch interview/meeting at the fancy seafood restaurant near my house and their offices. I’ll probably prove to be a terrible choice by ordering a burger.

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