I just gave notice at my job. Over the past four and half years I have learned a lot, but recently the rate of learning declined. More worryingly, I was no longer sure that the things which I was learning were relevant to what I wanted to do.

Worse still, I don’t even know really what it is I want to do. Do I want to write? Build a startup? Create a sales consultancy? Travel the world? Found an incubator in Kathmandu? There are just so many options and ideas. How can I find out without taking some time off?

Today it seems leaving my job is a no-brainer; but it didn’t always feel that way.

Over the past few months there have been so many questions and doubts:

Can one just quit their job without forever limiting their career opportunities? Is quitting going to isolate me? Is quitting to “pursue my dreams” quixotically naive? Would quitting brand me as an idealist who doesn’t live in the real world? Am I quitting out of laziness? How much money is enough to feel secure for awhile? Who are you to think that you can buck the trend and just stop working for awhile? Are you going soft in your old age, losing the iron-clad discipline that has been such a big part of your character these past few years?

These things started to push me towards paralysis.

Fortunately, I came across some unassailable wisdom from Marc Andreessen’s 2008 blog post on career planning. Career planning, he said is really about managing risk. Most people don’t think about their career as a bundle of different risks over 50 years. He goes on:

They might occasionally think this way, but they don't do it systematically. So when an opportunity pops up, they evaluate it on a standalone basis -- "boy, it looks risky, I'm not sure I should do it". What you should automatically do instead is put it in context with all of the other risks you are likely to take throughout your entire career and decide whether this new opportunity fits strategically into your portfolio.

It hit me that I wasn’t thinking about the risk of leaving my job systematically. I was looking at the risk of leaving while completely neglecting the risks of staying.

So I built a risk assessment spreadsheet. You can see it here in Google docs. A person with more math background would probably come up with something more sophisticated but I decided to build a simple model.

First, I wrote down every risk associated with leaving my job as well as those associated with staying.

Next, I decided to score each risk according to the following criteria:

Impact. On a scale of 1-5, what impact would this risk have on my life if it were to come to be?

For example, leaving my job carries some income risk. I would have to dip into my savings. But as a 28-year old with good savings, a very simple lifestyle, and a conviction that happiness comes from experiences, missing out on a year of income will have relatively little impact on my life in the long term. So I scored this as a “1" (being very conservative you’ll see that I actually marked it as a 2 in my spreadsheet).

Probability. How likely is the risk to happen? In the previous example, taking a year off from work carries a 100% income risk.

Another common fear is that by taking a step outside of the stream of steady work you are flagging yourself as forever unemployable. So I added the “Never Get Another Job Again Risk". It’s hard to argue that becoming forever unemployable would not have a 5’s worth of impact on your life. Of course, it’s also about 0% likely to come true. (Again you’ll see that for conservatism’s sake I gave this a staggering 20%).[1]

Mitigation. On a scale of 1-5, are there actions you can take to soften the blow of the risk or reduce the probability?

The idea here is that with certain risks you can work hard to make them more bearable or less likely. For example, I can mitigate income risk by doing part time sales consulting, or starting a boot camp or the fact that I will be working on potentially revenue generating projects - so it’s a 1. Compare that to the Learning/Skill Acquisition Risk which I scored that a 3 because while I can work to find the motivation to make sure I’m learning more, doing so would be decidedly swimming up stream. Whereas with the "Risk of, On Your Deathbed, Regretting Not Taking a Goddamn Risk That You Were Pretty Sure You Wanted to When You Were 29” mitigation is basically a 5 - there is nothing you can do.

I did my best to provide honest and accurate scores for each risk. Summing them up I determined that staying in my job was actually seven times riskier to stay in my job than it was to leave.

Looking at the spreadsheet, the risks that I associate with quitting are all relatively unlikely to occur and easy to mitigate with effort and resourcefulness. Whereas, the risks associated with staying in my job are well defined, understood and highly probable. This is the key driver of high scores associated with staying at my job.

Which leads to a surprising and counterintuitive insight: The very thing that makes leaving scary (the unknown) is the thing that makes leaving a lot less risky (there are so many more options and possibilities)!

Now, before anyone starts coming with pitchforks about the numbers I put into the spreadsheet, I will say that this is obviously a lot less scientific than it pretends to be. But the exercise’s value came from writing down the risks and thinking rationally about how likely they were to happen, how impactful they might be and whether or not I could do anything to mitigate them.

More importantly it forced me to think about the fact that there are risks on both sides.

Most importantly the absurd inadequacy of the spreadsheet made it obvious that I was probably over thinking this. Which made me laugh. And that is probably the wisest thing to do as you make these kinds of decisions.