Last week I finished a freelance gig that started in mid-July. It was an intense gig with long hours and many working weekends. On the weekends where I didn’t have to work, I was on call.
It was tough and stressful and often miserable. There were good times too and I met good people there.
I’ve been thinking in the last few days how I got through it. Because, honestly, without going into details, it was pretty miserable. And it meant not having a Chicago summer.1
Here are some of the reasons I didn’t quit:
- It’s only 3.5 months, anyone get through something like that.
- You made a commitment, keeping your word is important.
- The money is really good.
- I need the money.
- I don’t want to let the team down.
- I’m learning a lot.
- I’m working for an important cause; it’s important that I do my part.
Those are all good reasons, right?
What’s interesting is that depending on who I’m talking to, I might offer a different reason for why I did it. We tailor the stories we tell, depending on the audience, and I think for two reasons: one is to make the story more interesting and two is to make ourselves sound better.
The story you tell yourself about why you are doing it, that’s what gets you through.
And all of those stories worked for me at one point or another during the experience. But the one that persisted, the one that really kept me going was about the freedom. I’m sacrificing a lot of freedom right now for a lot more freedom down the road.
And sitting here on a Friday morning with nowhere to be and nothing to do, I have to say that I made the right choice. That sweet sweet taste of freedom, the freedom to work on whatever I want. I have about three to six months of runway before I have to take another job (assuming I don’t pick up any new freelance work) and that means I’m free to write every morning, for hours at a time.
I could jump on the train and fly to another city right now if I felt like it. I’m not going to, but I like the feeling.
I spent June directing a feature film, then I went to Scotland for a week in July and then started the job when I got back ↩
I’m reading through Pmarca’s guide to career planning on this lazy Sunday back home. Excellent throughout and way too much to quote, but some bits that ring especially clear:
The second rule of career planning: Instead of planning your career, focus on developing skills and pursuing opportunities.
I’ll talk a lot about skills development in the next post. But for the rest of this post, I’m going to focus in on the nature of opportunities.
Opportunities are key. I would argue that opportunities fall loosely into two buckets: those that present themselves to you, and those that you go out and create. Both will be hugely important to your career.
Opportunities that present themselves to you are the consequence — at least partially — of being in the right place at the right time. They tend to present themselves when you’re not expecting it — and often when you are engaged in other activities that would seem to preclude you from pursuing them. And they come and go quickly — if you don’t jump all over an opportunity, someone else generally will and it will vanish.
I believe a huge part of what people would like to refer to as “career planning” is being continuously alert to opportunities that present themselves to you spontaneously, when you happen to be in the right place at the right time.
Optimize at all times for being in the most dynamic and exciting pond you can find. That is where the great opportunities can be found.
Colin Powell says, “You know you’re a good leader when people follow you, if only out of curiosity.”
From the Pmarca Guide to Personal Productivity:
Let’s start with a bang: don’t keep a schedule.
He’s crazy, you say!
I’m totally serious. If you pull it off — and in many structured jobs, you simply can’t — this simple tip alone can make a huge difference in productivity.
By not keeping a schedule, I mean: refuse to commit to meetings, appointments, or activities at any set time in any future day.
As a result, you can always work on whatever is most important or most interesting, at any time.
Want to spend all day writing a research report? Do it!
Want to spend all day coding? Do it!
Want to spend all day at the cafe down the street reading a book on personal productivity? Do it!
When someone emails or calls to say, “Let’s meet on Tuesday at 3”, the appropriate response is: “I’m not keeping a schedule for 2007, so I can’t commit to that, but give me a call on Tuesday at 2:45 and if I’m available, I’ll meet with you.”
Or, if it’s important, say, “You know what, let’s meet right now.”
Clearly this only works if you can get away with it. If you have a structured job, a structured job environment, or you’re a CEO, it will be hard to pull off.
But if you can do it, it’s really liberating, and will lead to far higher productivity than almost any other tactic you can try.
As of last week, I’m self-employed and doing a version of this, along with some strategies I’ve picked up from Deep Work. I love it. My dream isn’t to retire and live on a beach; it’s to have the freedom to work on what I want, when I want.