Dear Captain,

I’m in my early 30’s. Having spent my 20’s doing the ‘right’ things (college -> law school -> office job), I have now recognised what was clear all along, namely that this is not for me at all, and that maybe that’s okay. I’ve also realised that maybe it’s okay to not be making the maximum amount I possibly could be, and okay to say ‘no thank you’ to the budding career I have zero interest in in favour of pursuing my passions.

Passions, of course, don’t pay very well, certainly not at first and possibly never. If I quit right now, today, I would be living hand to mouth with virtually no safety net. If I hold on for another 22 months, then I would have a very substantial safety net, enough to cushion me for a decade or more to come (I would still need to work to feed myself, but I would be able to absorb a good number of unexpected financial blows before going into crisis mode), plus put me in a better position in old age. There is no in between here.

Herein lies the quandary: I could die in six months’ time, in which case I would rather quit now and take my chances. On the other hand, if I did quit now and then didn’t die shortly afterwards, 2020!Me’s life is likely to be significantly more precarious and uncomfortable than it would be if Present!Me stays for the 22 months. I should add here that I tend to be a lot more productive in the creative area I want to pursue when I feel immediately secure, so this isn’t even just about my own comfort, but potentially impacts the quality of the work I want to do (and of course the point of this whole exercise is to give myself a better chance of producing quality work).

Knowing myself, I will probably do the 22 months. I don’t hate my job, have no reason to expect my imminent demise beyond the fact that it could happen to anyone, and the job comes with a fixed end date at the end of the period, so I’m less likely to fall into the trap of just putting it off and putting it off until it becomes too late. I’m just having a hard time reconciling myself to the ‘what if’ part right now right now. Help please?

My recommendation is that you work at your lucrative career for 22 more months and create the financial cushion that will give you the maximum amount of choices and freedom to do the thing you want to do. You will be setting yourself up to be maximally creative and happy if you have that cushion. We romanticize artistic struggle, but the plain truth is: POVERTY SUCKS. It is tedious and draining and boring and awful and limiting. It’s not cooler or liberating or inspiring. Don’t choose it if you don’t have to.

Since your email subject line was “I could die tomorrow, or I might not die for 50 years,” that’s not my only recommendation. You are thinking in terms of LIFE and DEATH and PRECIOUS TIME YOU’LL NEVER, EVER GET BACK. You need to get connected to your passions right now, TODAY.

Some ways to do that, listed in no particular order of importance:

Collect your heroes. Read Steal Like An Artist and choose your hall of virtual mentors. Whose art makes you want to make art? Dig into their work and read, watch, listen intently.

Read and choose your hall of virtual mentors. Whose art makes you want to make art? Dig into their work and read, watch, listen intently. Create rituals. Look into The Artist’s Way by Julia Cameron, and whether or not the “spiritual” language works for you, think about trying out her daily practices (free-writing three pages every morning) and weekly practices (The Artist’s Date, where you spend 1-2 hours by yourself exploring and giving yourself permission to daydream and absorb and create).

Look into by Julia Cameron, and whether or not the “spiritual” language works for you, think about trying out her daily practices (free-writing three pages every morning) and weekly practices (The Artist’s Date, where you spend 1-2 hours by yourself exploring and giving yourself permission to daydream and absorb and create). Get social. What is a professional group, MeetUp group, online community or other social network of people who do what you want to do? Join one of those and practice saying out loud to other people what it is that you want to do. “My name is ______ and I’m an attorney but I also _______ and want to be a ______.“

What is a professional group, MeetUp group, online community or other social network of people who do what you want to do? Join one of those and practice saying out loud to other people what it is that you want to do. “My name is ______ and I’m an attorney but I also _______ and want to be a ______.“ Find the local scene. Chances are that where you live someone is doing the thing you want to be doing with your life. Subscribe to the local theater company. Go to the local indie film screening. Get on the list for art openings at galleries, readings, humanities festivals. Sit on boards, volunteer behind the scenes if you can. In a careerist sense this is “building your network.” In a creative sense this is “filling the well.”

Chances are that where you live someone is doing the thing you want to be doing with your life. Subscribe to the local theater company. Go to the local indie film screening. Get on the list for art openings at galleries, readings, humanities festivals. Sit on boards, volunteer behind the scenes if you can. In a careerist sense this is “building your network.” In a creative sense this is “filling the well.” Give yourself permission to be a beginner. Is there an evening or weekend class in what you want to be doing that you could take? Try something out. Don’t put the pressure on yourself to be immediately supporting yourself with this creative pursuit. Experiment and play.

Is there an evening or weekend class in what you want to be doing that you could take? Try something out. Don’t put the pressure on yourself to be immediately supporting yourself with this creative pursuit. Experiment and play. Use your breaks . Do you get vacation time at this nice law job of yours? Can you plan to take some of it specifically around a film festival or artists’ retreat or concert or play you want to see? Plan out your vacation time over the next 22 months and make sure you’re giving yourself regular intervals to recharge and soak up what you want to do.

. Do you get vacation time at this nice law job of yours? Can you plan to take some of it specifically around a film festival or artists’ retreat or concert or play you want to see? Plan out your vacation time over the next 22 months and make sure you’re giving yourself regular intervals to recharge and soak up what you want to do. Use your hard-won education and skills in service of your future field. There’s a great organization in Chicago called Lawyers For The Creative Arts. Is there one of those where you live? Creative folks need contracts and all the “boring” paperwork that you’re trying to flee from. This is a way you can make yourself valuable, meet people, and start to transition your life toward where you want it to be.

There’s a great organization in Chicago called Lawyers For The Creative Arts. Is there one of those where you live? Creative folks need contracts and all the “boring” paperwork that you’re trying to flee from. This is a way you can make yourself valuable, meet people, and start to transition your life toward where you want it to be. Be vigilant about your finances. Maximize retirement contributions and anything your firm matches. Sock away as much money as you can in your FU fund. Shrink your living expenses so that they’ll be manageable during the transition time when you might not be earning quite as much. If you’ve got fancy health insurance, take advantage of it and get every nice thing you might want done now.

If you can start to connect to the work you want to be doing, I predict one of two things will happen:

a) It will make the next 22 months fly by, and you’ll be able to get through the boring days more easily because you know it’s ending soon and because you have good, creative, fun, nourishing stuff to think about.

b) Work will become even more unbearable by comparison and you’ll start hearing klaxons saying “GET THE FUCK OUT RIGHT NOW” so you will in order to save your own life. You always have that option any time, right?

Try one of the above suggestions, or all, or none as it makes sense for your life. Above all: Start the work. If there is a piece of work that is screaming inside you because it wants to be made, then get started, somehow, some way. That feeling you have right now that says “I have wasted so much time doing things I don’t care about already, how can I waste one second more?” is valuable, so use it, and don’t wait for 22 months to pass. But also, don’t eff up your finances and make life artificially harder for yourself because you think that “being a creative person” is some magical black & white special category that you have to burn your life down to enter. You’re already that person if you want to be. It’s not either/or, now/never. Just, start. Start in some small way to do the work you want to do.