2011 was a big year for me and since it represented a lot of what it means to be a Big Swinging anything I felt a post was in order.  To be clear, “big” doesn’t always mean “good”.  2011 was rough.  The startup that I had been working on for months vaporized in a matter of days.  I had the worst job of my development career.  I had clients who didn’t pay for months.  At the other end of the spectrum, I got to work a lot with one of the most talented developers I know.  I got coached by the most successful person I know.  Finally, I ended the year with an ideal client portfolio which should set up 2012 to be even bigger, and definitely better, than 2011.  Here are some things that I learned.

Give As Much As You Can, Then Stop

The year started with me wrapping up a contract that I had been on for more than a year and jumping back into the startup world.  I had been working on the startup during off-hours for a couple of months and had picked up some great new skills (MongoDB, IronPython, ASP.NET MVC 3, etc.)  I had negotiated my ideal combination of great salary and good equity stake and was ready to work on the company full-time.  I had no problem working for free for several months and paying some travel expenses because I really wanted to make the deal happen.  Then, it all unravelled in the course of a few days.  The partner on the business side decided that the salary I was asking was too high.  This was months after I thought we had agreed and after this partner had told our only investor that he wasn’t needed.  In the past, I probably would have compromised to make it work since I had already invested a bunch of time and effort, but I’ve matured since then.  The combination of recognizing sunk costs and having an unwavering requirement that I trust my partners led me to withdraw.  It was hard (and somewhat scary) to abandon the path that I had committed myself to for many months, but I had given all that I was willing to and once I was asked for more it was time for me to stop.  Since I had set a “if I don’t have signed paperwork by this date then I’m out” deadline, it was clear that it was time for me to leave even though it wasn’t easy.  Know what you’re willing to give, but be honest enough about it that if you’re asked for more then you stop.

It’s Hypocritical To Not Get An Outside Perspective

After leaving the startup path, I needed to figure out what was next.  Quickly.  The nervousness of not having work lined up really drove me.  Crazy.  The problem with being both driven and crazy at the same time is that you thrash.  You end up expending incredible amounts of effort for near-zero progress . . . or worse.  I was fortunate in that one of my business partners is an incredible coach and he made it clear that we needed to talk.  I don’t remember anything we discussed during the hour except him saying, “With options comes power.”  My problem was less about not knowing what to do and more about *needing* to do something. I took his overall advice of “get a few clients who will pay so you’re not dependent on any of them” and started working on my client portfolio.  After I got things back on track I realized how hypocritical it was for me to not seek an outside perspective from the beginning: That’s a big part of what I sell!

Find Enough Clients Who Can Pay

For the rest of my career, I am likely to have at least 2 clients.  An ideal number for now is 3 or 4, but it takes at least 2 in order to have options, and therefore power.  One of my clients is a startup and startups sometimes run out of money.  There’s a big difference between a client who is unwilling to pay and a client who is unable to pay.  If they’re unwilling to pay, the relationship has probably been destroyed and things quickly turn into strictly business decisions.  If a client is unable to pay, however, things are a little different.  It is in the nature of startups to reach beyond their grasp and sometimes they fall.  I happen to really like this particular client so I checked in with them once a month, but never in a mean or threatening manner.  Because I had other clients who *could* (and did) pay, I had the option of waiting.  It took a good 3 or 4 months, but they raised another round of funding, sent me a check, and we’re back to working together.  If I had been demanding or unpleasant during their inability to pay, we probably wouldn’t be working together now AND it wouldn’t have changed the fact that they couldn’t pay.  If you have enough clients who can pay, you have the option of working with some who may not . . . and they’re often the most enjoyable.

The Happiest People I Know Are Where They Put Themselves

I read a lot of blogs and talk to a lot of people about their work and their lives.  One thing that really crystallized this year is that people who are in a place intentionally are much happier than those who have “ended up” someplace.  And it’s not just the rich ones who started something that became big, it’s also the folks who decided what they wanted to do with their lives and set themselves up around that.  This is sort of an extension or evolution of, “Do what you love and the money will follow” because I think that that phrase needs a bit of updating.  I’ve seen plenty of people who love technology or software development, but are f’ing miserable because they’re in a situation not entirely of their choosing.  Chances are you know someone like this.  He liked computers and software and learned to code.  He found a job somewhere because he needed a job and things were somewhere between fine and great in the beginning.  Over time, he got worn down by the company environment until he ended up with a position he would have never consciously chosen.  But he’s stuck.  He’s afraid to go somewhere else and now he’s just kind of “ended up” doing what he’s doing.  Contrast that with someone who has created her own position to do work she enjoys, even if it doesn’t pay a lot (as long as it’s “enough”).  She’s invested in making things work.  She’s set up her work to integrate with her life.  And she has options.  If things don’t work the way she thought, she can always redesign and renegotiate the position.  She’s there by choice and since she chooses to do what’s she’s doing she’s better at it and happier overall.  When I find myself in a job because I need it, it’s not very long until it starts to wear on me.  When I’m working on a project that I helped create, however, I’m committed to it and energized by it.  I’m not suggesting that choosing your work is the answer to all your problems or the one true path to happiness, but I have observed (and lived) that people who consciously choose their work are happier than those who don’t.

Here's to a Big Swinging 2012!