How I Decided Now Was the Time to Become Self-Employed

Ball and ChainA little over a month ago, I quit my fulltime job to focus on Light Point Security. While I always envisioned eventually working full time on my own company, I did not imagine I would be doing it so soon. Even a month before I quit, I thought it could easily be a whole year before I would be ready for that. I thought it would be fun to write this article to express how/why I decided to quit now, and how my first month of self-employment has been.

Why Now?

Like I said, a month before I quit, I had no intentions of quitting any time soon. While I had dreamed of one day quitting and being my own boss, I had always planned to do it after Light Point Security was generating substantial income. So why the sudden shift and deciding to quit before we have even launched?

In late January, on a Friday evening, I had a discussion with one of my bosses. I had suffered from burnout pretty bad last summer, and took an unpaid month off to deal with it. The discussion sort of focused on seeing if it was happening again, because I didn’t seem to be very engaged anymore. Well, there was a serious miscommunication in this discussion. The boss left thinking he had given me a pep talk to get me back into it, and I left thinking I was being politely fired.

Like I said, this was on a Friday evening, so I had a whole weekend to stew on it. On Friday, I was worried. By Sunday night, after thinking of all the things I had done for the company, I was pissed! I also spent that weekend wondering what to do. Beg to keep my job? Go hunt for another? Or maybe just focus on Light Point Security fulltime?

Decision Points

I needed to decide if going fulltime on Light Point Security made sense. The root of the decision came down to this: could Light Point Security pay for me to live before I ran out of money. I calculated how much money I spent to live. This was for home mortgage, utility bills, food, and a little leisure money to keep from going insane. Lets call that total X. To decide how long I could go without working, I added up all my liquid assets. I did not count retirement accounts because I don’t believe it would make sense to pull from that. Lets call my liquid asset total Y.  So Y divided by X would tell me how long it would be before I went broke if I made no more money. My total came out to about 3.5 years.

Then the question is: am I willing to sink ALL of my savings into this. How long will I go before I decide it would be smarter to give up? I decided that I could give it 1 year. After 1 year, I would reevaluate where I was. If it looked like this was going to work, I could keep going. If I thought by that point it wouldn’t work, I would not be ruined. Because of the area I live in, I could get another job like I had before in a couple days. I would have spent less than 1/3rd of my savings. I would not be in extra debt. So it seemed financially reasonable to consider it. If it didn’t work out, I would still be fine.

If this had happened a year earlier, I would have made a different decision. A lot of startups these days are websites. Most of these sites can be set up and launched within months. So a lot of the popular advice for startups is to quit your job immediately when you start working on one. Light Point Web is a different beast. It is much larger and way more complicated than building a website. A year ago, I would have probably decided that I could not have it finished in time for it to gain traction before I ran out of money. This means it does not make sense to go all in yet. However, when I looked at my current progress, I thought it was very likely that I could have Light Point Web done soon enough…especially if I was working on it fulltime.

So the decision was made that now is my time to go fulltime. I spent the whole weekend convincing myself of this, and by Monday morning, I was confident in that decision.

The Fallout

When I went back to work on Monday, the boss wanted to have a follow up meeting. It was in this meeting that the miscommunication was cleared up, and they had no intentions of firing me, and they very much wanted me to stay. But it was too late. I walked into that meeting confident it was best for me to quit. The damage was done. So I followed through, and put in my 2 weeks.

Looking Back

So I have been self employed for just over a month now. Simply put, its great! I get to work on what I love, whenever I want. While we still have not launched yet, we are soooo close! I’m working quicker and more efficiently than ever. I feel so much healthier. As I am writing this, the rest of the world is in their cubicle, and I am sitting out on my deck enjoying the sunshine. When I think about it, I’m really not sure if I could ever go back to working for someone else. I suppose that is more motivation to make this work.

How about you? Have you taken the plunge yet? What made your decision. What is holding you back? I would love to hear from others who have gone through this.

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