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Be Prepared to Lose

Written on June 17th, 2008 at 8:29 am

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Nearly four years ago I swore off any and all future work for myself online because of a client. We’d figuratively played a game of chicken and I lost. For about a year after that I stuck to that decission and didn’t take any more freelance work.

I wasn’t prepared to lose. In the game, whether that be life, love, work, or taxes, you win sometimes and you lose others. To win in the long run, you have to be prepared to lose.

Quick thought: don’t play the taxes game. The banker knows when you cheat!

In October 2003, I started a short lived relationship with a client. I was developing what amounted to an AJAX powered website slightly before the AJAX revolution began. I started this project off on the wrong foot by quoting myself short on both time and cost.

These type of losses are only short term and can often be corrected through appropriate communication. If the budget that was planned turned out not to be enough, tell the client and attempt to work out a solution that is satisfactory for both sides.

That doesn’t mean you lost in the game though, you simply fell behind. I fell behind.

I continued to fall behind with missed deadlines and procrastinated work cycles.  We worked out a satisfactory solution where the project was completed on a longer timescale with the same budget.

This way I was able to focus on other work besides this project as well.

The project concluded in March. What was originally a two week project turned into a 3 and a half month long marathon.

I’d already been paid half of my budget in the beginning of the project and at the half-way point. I lost the game after handing over my work and my opponent chose not to pay me the second half of my budget.

I felt degraded, cast out, and pretty much like shit for a few months following. That was worse than not being paid what I was due.

Prepare Yourself for Failure

Playing chess, you usually don’t throw out a piece undefended. Your queen might be attacking but your bishop is right there backing her up.

Don’t leave your work defenseless. Prepare a good contract that will back you up when your opponent decides to play against the rules. Verbal or email contracts aren’t accepted as valid in all countries/states so make sure it’s in writing.

Even though you may have safeguards in place like an all-binding contract, you still have to prepare yourself to lose.

Your next project shouldn’t be an end-all be-all. What I mean is, if this project were to fall out from under your feet, you need to still be standing. Like wage earners who work from paycheck to paycheck, we freelancers often can fall into the mistake of living from project to project.

But placing ourselves in that position gives the client power over us. It’s unnecessary and only limits your potential as a freelancer. it doesn’t prepare yourself to lose but simply places hope, often false, in a win.

But hope, even if it’s not false, is not good. You can’t hope that you’ll be still working from day to day. Measures have to be taken to ensure that you still have your line of work tomorrow.

Work on multiple projects at once. Client often like to “own” you while they’ve hired you for work although if you let them then you have nothing to fall back onto if they decide to force a loss upon you.

Not Being Prepared

My brother is 13. He made a flippant bet with a friend the other day. It turned out that he lost and was forced to wear fingernail polish for the rest of the week. He wasn’t prepared to lose. He hadn’t expected to lose. His friend had only won by a slight margin which made it even worse.

At the dinner table when we noticed as he was trying to hide his fingernails by pawing the serving spoon is when he lost. He lost all scrap of manhood we had left for him. Admittedly, it was a pretty ballsy bet to make on his behalf.

What he was afraid of was losing the one piece of manhood he had attached to our other brother. He simply adores him and tries to be like him. He told me, he’s going to make sure he does not find out.

Thinking about what he said, I realized how prepared he really was. He knew what he needed to protect and where it was ok to cut his losses.

I learned how to lose from my younger brother.