What would you do if you were me?

[tony_elk]

I feel as if I'm stuck in a no-win situation in my career, and I'm wondering HN readers, what would you do if you were me?

Here's my story: I'm in my late 40s and have been involved in information technology professionally for my entire adult life (and even did board-level repair of early personal computers when I was in high-school). For the past 20+ years I've been involved in IT audit and information security as an auditor and consultant, and as an information security manager. I'm technical enough that I'm currently a security-architect / sales-engineer for a large telecommunications vendor. I've tried two startups in the past (mobile robotics and security consulting). Neither were overly successful, but I learned a lot. I currently live in the upper midwest, am married (for 20+ years), have three children (ages 12-18), and make a decent living. Sounds great, right? I should be happy.

Here's the problem: I'm not making anything! I'm not creating! I strongly feel I'm a "Maker", a "Developer", but I may have realized this too late.

During the evening, I program for fun (mostly Ruby on Rails, these days, but Lisp, Python, C, and micro-controller assembly in the past). I'm not the greatest programmer, mostly because I can only do it a few hours each week (let's say ~10 hours per week), but I can get by. And, I really enjoy it. So, I'd like to do more programming. And, I'd like to do another startup. I have SaaS B2B application in mind. But, it seems at my age it is going to be impossible to shift from my current career to a programming career or to do another startup because the lifestyle change (read "drop-in-income, at least for a while") will be intolerable, especially for my family. Does that mean I'm done? Game over? At this point, am I doomed to sitting on the side-lines and only watching or being a cheerleader to other developers and startups? What have other professionals who have been in my situation ("golden handcuffs") done to get around this? I've had a successful career (especially for someone who didn't complete college), but with three teenagers, it's not like I have a stash of cash available to make the transition.

What would you do if you were me?

[djt]

What I did was start small and learn the skills and grow my income from my "hobby bUsiness" until it became equal income to my day job. At that stage you will need to decide which way you're going to go. Stay safe or go with your passion. Also read up on all the other parts of running a business such as accounting etc, there are lots of good links on HN about this kind of stuff, It's invaluable.

[kls → djt]

I would second this, start a niche interest in a hobby or passion of yours. Try to grow it to create a phased transition out of your current situation. Having a secondary interest can also help avoid burn out, which you may be experiencing the first phases of. If you have hardware and embedded experience you have an advantage. Most developers are pure software technologist. There is a lot of money out there looking for hardware/software innovations. Embedded can be lucrative as a side venture.

[moocow01]

Well this may not be the most tangible advice but I'd consider trying to consolidate your efforts where you can identify them. Is there anything having to do with your current situation that you could integrate/leverage with your desired direction? Examples of such things...

- Asking your employer to take you on as a contractor - this could allow you to likely make a similar living and start transitioning your work efforts toward building a business that could produce services for your employer (B2B) as well as other companies in the same domain.

- Taking the remnants/assets of your past startups and using them to jump start a new one.

In essence Id work on making gradual transitions towards aligning yourself with what you want to do. Start small as others have said - try to first figure out how to make a dollar then figure out how to make 2. Honestly I wouldn't just go blindly jumping off the entrepreneurial cliff unless somebody else's money is carrying you. It sounds exciting until you realize the ground is approaching faster than you can figure out how to fly.

[brudgers]

You program for fun? My advice, put more fun in your life away from work.

You're in your late 40's. Odds are you have more than half your adult life remaining. Your kids are growing independent, let them see who you are as an adult beyond being dad. This will also give them an example by which they can develop their own identities.

According the Silicon Valley meaning, a consulting business would not be a startup, unless your SaaS-B2B scales well, it will not be either. Even if it does, it is probably so far within your comfort zone that the current lack of a demo may indicate the degree to which you feel passion for the idea.

Forget this as a career decision, so long as you frame it that way, a good paying job is the most effective answer.

Focus on what's import in life.

And have more fun.

Good Luck.

[AznHisoka → brudgers]

I agree to a degree. OP: Do you think your family life is as fulfilling as it can be? Are your feelings due to something else missing in life?

[brudgers → brudgers]

By "more fun" I mean program more.

[wayneyeager]

I would use the spare time (10 hours a week you said) to develop a prototype of your application. MVP, etc. Keep your job, and start out small with your side project.

Work on it until someone will pay you to use it. Over time, improve it, get others to pay, etc. Repeat until you can you reasonably devote yourself to it full-time.

If your app/idea/situation doesn't lend itself to that sort of organic growth, then you've no choice but to roll the dice and go big, or stay where you are. But since rolling the dice sounds unlikely, I'd contort myself and my idea as much as possible to fit into the grow-slowly-as-a-side-project paradigm.

[Source: my experience. This is what I did to launch my first biz. Grew slowly. Company got acquired.]

[rcavezza → wayneyeager]

I agree completely with Wayne Yeager.

More than that, I'd probably use some type of landing page technique to help gauge demand for your top 10 ideas. Create simple landing pages with a tool like unbounce to see who will click the signup, download, or buy buttons for each idea and drive targeted traffic with adwords.

This is probably the easiest way to narrow down to your best idea w/ some market validation.

[jnorthrop]

I am you! Well almost. I'm also in my mid-40's, 20+ year IT professional with a family and a good job. I was feeling very much the same way you are until about six months ago. That's when I got off my butt and started two things.

1. I'm currently looking for, and finding, speaking slots at conferences. It's fun and I get to play the expert for 45 minutes.

2. I started a side project[1]. I don't expect it to make money but again, I'm having fun with it.

Give it a go. What I'm doing costs very little and has given me some new energy.

[1] My side project (http://wodwatts.com). I just pushed the landing page public this morning! It's not quite ready for prime-time but I hope it inspires you.

[KoryFerbet]

Depending on how long you've been at the company, this may not be an option but I've seen it before, is there a way that would allow you to work from home one or two days a week? Or maybe work four 10 hour days and have a day off. This would give you an extra day, or some extra time to work on your own side personal projects. Don't ever let yourself quit innovating! If you have an idea find a way to make it work, especially if you feel it's your true calling.

[kenrik]

My question is why don't you think your family would be supportive? I think that's where you should start, after you get that figured out I would suggest you explore the possibility on the side at some point you should "know" which direction to take. You need to keep your family in mind however you only have one life so if I were you I would at least explore to see if you can make some changes that would make you feel fulfilled.

Maslow’s hierarchy of needs:

Physiological Needs - Security Needs - Social Needs - Esteem Needs - Self-actualizing Needs <- This is what you feel you're "missing".

Good luck!