Scared of Success and Failure…

Mortgage payments are important, some might say they are top of the list kind of commitments……..I would have to agree with that. There’s nothing like having a roof…then not having a roof. A roof is stability in more ways than one and in a way, that stability rules our lives. We work hard to keep life stable. We stop working hard, our lives just might topple over. I can’t tell you how many times I have considered making a bold move in the interest of a better, happier direction in life, but shy away from it because the short term stability may be put in Jeopardy. Just to clarify, better and happier is not money in this conversation. It includes money, but is not about the money.

I have been in some way shape or form connected to the computer / internet / networking / web development industry for a dozen years now. I am not a master of anything, but am pretty good with a bunch of different things. I have been considering my future and what I want to do with the experience and interest I have. I decide a long time ago that working for myself is my ultimate goal. I have been thinking about my plan of attack for at least five years now and wonder if the leap is near… I am so close to jumping ship and swimming for it, but the water looks mighty cold and the coast looks so far away.

I have had some preliminary success in working my way up to working for myself, but the next step is a big one and the two options I am faced with are not ideal. To keep the stability, I must make what I make now, more or less. If I jump and swim on nights and weekends only, my family may not see me for a while. If I pitch a hybrid role to my boss, I may find myself with a stay or go situation, which would smash my plans of working for myself RIGHT NOW. The problem is that I have enough of a word out that I can make one move and just might get swamped with work and I am scared of that. If I go with the night and weekend business plan, I need to be able to set aside some time for family and I am scared that the new business would suffer if I do that.

So what am I to do? Not interested in small business loans or anything like that, don’t want to leave my company high and dry, don’t want to go on family hiatus, but don’t want to put off my goals for much longer…….

Apparently I am in a pickle, and I’m not particularly fond of pickles…


19 Comments on “Scared of Success and Failure…

  1. What do you want to do? I’m in a similar boat and it sounds like we have similar backgrounds, i.e. IT-related. Feel free to drop me a line.

  2. Kamen – awhile back I quit a job under good terms, and from it, I actually picked up some contracting work doing what I did full-time… now mind you I’m not trying to work from home full-time doing my own gigs or anything… but is there anyway you can put out some feelers from anyone else you work with and see if what the water would be like if you did pursue some PT setup (or whatever you mean by “hybrid role”)?

    Would you have any other possible options for work if you tried going toward this hybrid role? Any possible contract opportunities if you had to? Backup plans are always good, especially if you don’t have to take it unless you really have no other option…

    Keep us posted.

  3. I totally forgot it, but have you tried fried pickles? Especially cajun-flavored… they are totally different and really good 🙂 Now if only I could find out how to properly fry one to make it taste like that!!

  4. Wouldn’t it be so wonderful not to ask permission to stay home when you’re sick? I want to be like Heather Armstrong from Dooce. Her whole life is blogging? Sign me up!

  5. Kamen, I faced the same challenge and with three teenagers rapidly approaching college, the income pressure was there. Similar to what Chris mentioned, what I was able to do was find a consulting gig (through my network) that I worked four days a week and since I was able to charge slightly more than I would have made normally, I could make *almost* as much, but it left one day for me to work on my own ideas. It worked. Having that one day to focus on my ideas was enough of a bridge for me to line things up and jump! Good luck.