What if you aren’t content with working for someone else your entire life?

Some people thrive when working for someone else.  Having that security and stability enables them to focus and do their best work.  But if that’s not you, going to someone else’s office to sit in a cubicle could drive you slowly mad.

Even though you know the money isn’t bad, even though you are making good connections and friendships.  There’s an itch that won’t go away, so long as you don’t have full control of your work (and it’s actually deeper than that — it’s about controlling your time).

So what sort of mindset does it take to start your own business?  Or at least to find a way to work on your own terms?


What Does It Look Like?

I’ve been working on a startup part-time for the past year.  A friend recently asked me for advice, since he is somewhat entrepreneurial himself.  He sent me his plan and asked for feedback.  Here’s his general plan:

1a. work for 2-3 years, save money, develop skills and reputation
1b. continually use free time to work on side projects that might have value
1c. build up a social/business/industry network
2a. kickstart/VC/angel funding to give an idea time to incubate
2b. find talent
3. ride as far as possible before looping back to step 2 (or 1, depending how bad things went)


He also asked how to do these things without driving a significant other crazy in the process.  Smart man!

I think this plan isn’t bad.  I’m not an expert, since I’m still going through the process (as of this posting, no IPO yet!).  But I have learned some things that I think are relevant.


A Healthy Approach to Startups

First of all, I completely identify with not being content to work for someone else forever. I definitely feel that way, and that’s a big part of what drives me to work extra hard now so that some day I will be the one in control of my time and work schedule.

With that being said, you have to be careful not to start resenting your current employer just because you haven’t “broken free” yet, so to speak. You always need to appreciate your co-workers and your managers, not to mention the company itself that is providing you with a paycheck. As my friend said, you are fortunate to be where you are right now — employed and gaining experience every day. It’s good to see a plan that is realistic in the sense that you know you need to work for a couple of years to build up contacts and experience. Unfortunately, “overnight” successes don’t happen overnight, as I’m sure you know.

So yes, focus your energies at work right now getting to know your co-workers, and diving in to your work. Try to avoid the feeling of “this-is-just-a-job-I’m-doing-for-a-while-until-I-have-a-startup-so-I’m-going-to-just-do-it-and-move-on”. The more you work to truly understand the “why” and “how” of your job (instead of just the “what”), the better off you’ll be. And your co-workers will see your work ethic, your commitment, and they’ll see someone they would potentially be willing to work with someday….

You’d be surprised how connected people in an industry can be. The more you network and meet people, you’ll begin to see the web unfold. It does take time though, to be sure. For the first couple of years you may not even notice a difference or feel like you’ve met too many people. But I think there’s a tipping point where you’ve met enough of the right people who themselves are well-connected. And that’s when it’s off to the races!


Is It Time for Investors Yet?

Before you get to the funding stage, you have to have made some good connections. And you have to know people beyond your specific role — meaning don’t just network with other programmers. That’s good, but you also need to get to know marketing and sales people. Because you might have a world-class programming team that makes a ground-breaking app — but without somebody to help you sell it and get it front of the right people, it will flop.

Knowing someone with experience raising capital is a huge plus as well. In general, try to surround yourself with people that are smarter than you. Once you have enough of a team in place, and a solid idea in place, only then should you try to raise money.

People won’t give money (crowd-funders or angels) without some sort of demonstration of an awesome idea that has significant income projections. Crowd-funders might get wooed by neat features, but angels won’t give money unless you show the income potential (through revenue or buy-out, doesn’t matter). You need to have both.


Is It Hard to Find Talent?

It’s actually relatively easy to find talent, especially if you’ve done a good job with the previous step. This is probably one of the easiest parts, in my opinion.

Between you and your teammates, if you’ve networked well, you’ll have lots of good starting points.  And you’ll have the added bonus of offering something unique to work on.

Working for equity is actually quite attractive to a lot of people (especially if they already have a day job to pay the bills).


Riding The Wave?

Hopefully you’ve picked an idea that you’re passionate about, and that you’ve refined in earlier steps to chart the best possible trajectory toward success.

There are many stories of startups where the founders were eating ramen in their apartment and not sleeping trying to make things work, and at the last day of the month before rent was due things finally took off.

That makes for a good story, but it’s a great way to run yourself into the ground (physically and mentally). If you plan well, that shouldn’t happen. Yes, you should push through and not give up too early, that goes without saying.  But if somehow the game fundamentally changes and your plan is now useless, then (and only then) should you throw in the towel and go back to square one.


Be Your Own Worst Critic

Ideally, you should pick apart your idea so thoroughly in the early stages before you ever get any funding. That part is hard, because it feels personal having your idea criticized or changed. But if you can fill all the holes in your plan up front with your small team, then everything else becomes much easier later on.

You want to avoid unpleasant surprises when some random friend asks you “okay, but what about <some-thing-you-totally-overlooked>?” You’ll be scrambling much less, and your chance of success will be much higher.

So pick at your idea early on. If it can’t stand up to scrutiny, it isn’t an idea that you should be spending years of your life on.

With that being said, no startup is a guarantee, even when you plan well and work hard. So be mentally prepared for if your startup doesn’t get off the ground. I’ve heard that only 1 in 10 businesses really succeed, so that early work and planning is key to improving your odds of success. And if the first one fails, make sure you learn the lessons before starting again, because that experience will be invaluable.


What If I’m Not Single and Responsibility-Free?

Managing a startup with a significant other (SO) in the picture certainly make things different.  (I’m assuming you want to maintain your relationship with your SO…)

For starters, try to erase that picture of the guys in the apartment eating ramen and coding all night. That’s not going to be you. You need to be proactive about scheduling your time to work on the startup, and also leave time for your SO as well. You don’t want your SO to feel less important than the startup.

Yes, things might take a little longer overall — but in the long run, that’s not a bad thing. It helps to have that measured plan, so you can make steady progress while not totally neglecting your SO.

To get into my productivity groove, I wake up early. My wife likes to sleep in the morning, so it was perfect for me to get in a couple hours of work each day. Then we would both go to our day jobs, and I would keep the evening free for spending time with her (or going out, doing things together, etc.).

Your schedule might be different, but this way I knew that I could promise at least 10 hours a week to the startup. Your schedule will probably be different than mine (you may be able to find 20 hours), but that’s the general idea. It also helps if your fellow team members have SOs, because then you don’t look like a slacker by comparison (in terms of number of hours worked).

Your SO might also be concerned about money, and might not be as adventuresome/willing-to-take-risks/entrepreneurial as you. That’s okay — it helps significantly if you can keep your day job and work on the startup in your spare (scheduled) time. That mitigates the risk in the mind of your SO, since they still see regular income coming in, and don’t have to worry about what would happen if the startup doesn’t work out.

In my case, I’m not going to quit my day job until my startup has enough money to pay me a salary for at least a year. That helps put my wife more at ease.


Other Thoughts

As you can imagine, you’ll need to get good at time management and finding balance. For your day job, do your best to keep a regular schedule. Don’t stay late every day. Do your best while you’re there, but unless there’s some important urgent deadline you know you should help with, go home at a consistent time.

Cut out unnecessary time sinks as well — things like TV and gaming. If your startup idea is interesting enough, you won’t miss them.

You may also need to cut back on standing commitments (I stepped down from a church ministry for the time being) so you can focus and not be pulled in too many directions.

For example, I don’t recommend you try to run a blog in addition to your day job and your startup (I didn’t intend for that to happen with me… but it did). Because that’s time I’m not spending on the startup.  (Don’t worry, Life In Charge isn’t going anywhere!)

So you want to streamline and simplify as much as you can. And yes, schedule in rest, because otherwise it won’t happen. For me, I try to keep Sundays as non-work days.


Okay I’ll Stop Brain-Dumping Now

At any rate, those are some thoughts on how to approach a startup while maintaining balance and upholding many of the principles we talk about here at Life In Charge.

Starting a company isn’t for the faint of heart, as it does take a big commitment of time and energy.  But the payoff can be very rewarding — not just financially, but for the freedom of finally being in full control of your own time.

Have you ever thought about working on a startup?  Leave a comment below!