When You Planned Your Year, You Sure as Hell Didn’t Plan THIS


When You Planned Your Year, You Sure as Hell Didn’t Plan THIS


Updated January 2022

The Design Your 2022 Workbook has now been released!


Holy shit, 2020 has lasted well into 2022.

At the first Bullish Conference in 2013, I held a workshop called “Design Your 2014.” There was a workbook, about 8 pages long, distributed on clipboards, which the participants were told to take to the pool to complete. What fun! What luxury!

The first Bullish Conference in Miami


We reconvened, we workshopped, we designed the shit out of our 2014. One of the sections in the workbook is about asking for help – brainstorming who has what you need to fulfill the goals you’ve set out, when and how you will ask … and then actually asking one person. Like, now. One person pulled out her phone, asked somebody for something, and eventually got a book deal.

Since then, the workbook has gotten longer and more thoughtful, adding sections on making a “to-don’t” list and getting your friends and family onboard with your goals. It’s been rereleased every year since.


Great, wonderful, rah-rah, you can design your life, you fancy bitch! Book deals for everyone!



I wrote the first version of this post in 2020, around week eight of most Americans quarantining in our homes. Since then, some things have reopened; some have reopened that shouldn’t have. We’ve been through multiples waves. Schools are frequently canceled. Is it even safe to have childcare? We are, in many ways, all fucked. Whenever you’re reading this, things are probably still fucked.

Making plans is a goddamn challenge. It can seem futile.

So can you “design” your lifestyle? Can you live out the 2022 you planned?

I recently received the following question:

Jen how do you stop thinking about death every day, it used to make me live life with intention but now it just PARALYSES ME SO STRESSFUL

And my answer was: sometimes it’s just not the time to live life with intention. That’s a tool, not a virtue in and of itself.

Look, once I jumped out of an airplane.

I had taken a full-day skydiving class while working towards a certification, and my assignment for this jump was to practice my tricks in freefall – piloting my body like a little airplane, belly to the ground, arms like wings of a plane. You can actually steer yourself like a tiny airplane while hurtling towards the ground, by physically arranging your body parts in an airplane-like shape! Physics!

So, I jumped out of the plane. My instructor jumped at the same time, watching me from eight or ten feet away as we hurtled towards the ground.

And I was so determined to do all my cool moves that I FORGOT TO PULL MY FUCKING PARACHUTE.

You can’t talk in freefall. It’s like sticking your head out of the car window on the freeway, but moreso. My instructor had a device on her wrist that tells you how far you are from the ground and therefore when you need to pull your fucking parachute. She tapped it exaggeratedly until I got the message.

We survived. I flunked the lesson.

Maybe now is not the time for your cool moves.

Maybe now is the time you are hurtling towards the ground. And maybe actually everything is sort of fine – you have a parachute, it works, you’re very likely to survive, you certainly feel very privileged compared to anyone who doesn’t have a parachute. But falling safely to the ground is all you can do.

There is a time for everything, if you’re lucky enough to live a long life.

There are times of relative safety and prosperity in which you don’t want to just let life happen to you. How terrible! How mediocre! What a waste of your vim and vigor!

And then there are times when life just happens to you. You cannot execute your cool moves. You will not be steering yourself like a little airplane. You will not get a six-pack and teach yourself Python.

Sometimes it is simply time to have an experience. To live through something. To help yourself and others when you can.

If your goal is simply to have a full human experience, it is hard to fail.

You might feel a little less anxiety if you make that your goal.


How Does “Design Your 20XX” Still Work In a Crisis?


Look, the last part of Design Your 20XX is “now make a plan!”

Maybe don’t. But the whole concept of Design Your 20-whatever is that

  • Your lifestyle design should come from your values
  • Your values can include avoiding you DON’T want; it’s okay to hate things
  • We live interdependently with others: who can help? Who are the stakeholders you need to buy in to your plans?
  • You can’t know exactly what your future self will want, but your future self will always want resources and options

These principles still apply more than ever. You can still ask yourself these questions – seriously, alone, with pen in hand.

Define Your Values

Page 5 of the worksheet asks you to define your values. I ask you to do it realistically. Maybe your highest value is “justice,” but on a day to day basis, you spend a huge amount of time thinking about sex. Cool. That should be part of your values. It’s fine if you end up with “end voter suppression; flawless eyeliner; take care of my parents; feel like a badass by being acknowledged at work.”

The point of defining your values is that they are under your goals and plans. When goals and plans wash away, your values are still there. You can put new plans – or maybe just very small actions – on top of them.

Make a To-Don’t List

Page 13 asks you to enumerate a list of bullshit up with which you will not put.

If you’ve been home, probably some specific kinds of bullshit have dissipated on their own. When’s the last time you were sexually harassed on the street? Fewer traffic jams, less commuting, no one taking your sandwiches from the work fridge. But new forms of bullshit may have arisen.

It is often easier to avoid bullshit than to bring to life some grand new plans. Our lives have been cut down to less. Go with it. Identify and cut out all the bullshit you can. That includes some whole-ass people who may be using a pandemic to show just how shitty they can possibly be. Cut them out. Toss them in the bin.

Who can help? (Maybe it’s you!)

Are you better or worse off right now than most people you know? If you need help, who can help? (This is page 10!)

Asking for help can cause anxiety, so it can be helpful to soberly make a list of what you need or want, who can help, and when and how you will ask. Maybe it’s too much all in one day to acknowledge that you need help, figure out who to ask, and then work up the guts to do it. Instead, we make a little chart. We plan to send an email on Tuesday, and make a phone call on Wednesday. That sort of thing.

If this doesn’t seem to apply, you should probably be doing the helping. Helping people proactively when you can usually comes back at you at some point. It’s a good way to redeem the rest of this year of hell.


Captain Janeway felt it too.


Your future self wants resources and options

From page 16 of Design Your 20XX:

You might be a very different person in ten years, but that future self will not regret having an emergency fund, owning property, having residual income, or an impressive savings account. That future self won’t mind having a reliable vehicle, a current passport, people who can watch kids, pets, or other dependents as needed, and whatever else is needed to secure whatever passes as freedom in our society.

Help your future self out. Your future self is a bit of an unknown to you, so imagine you’re trying to set up a kind stranger, building on the resources you have now.

It is always true that we are poor at imagining what our future selves will like and want. This is why your closet is full of purchases that seemed like good ideas at the time.

But now, not only do you not know what your future self will like and want, you don’t know what kind of world they will live in. I mean, you never did, but surely you didn’t foresee this.

Survey the devastation! If the devastation hasn’t hit you personally, survey your couch! You have probably seen a lot of it lately.

Imagine all the other lives you could be living. Maybe your dense list of three dozen goals during some halcyon year of the Obama presidency was exhausting but also small. Maybe it’s time to be a civil rights activist and not care as much whether you get that promotion. Maybe knowing you can’t leave the country makes it clear how much you want to. Maybe your job is stupid and doesn’t need to be done in the world at all, by anyone. Maybe you want a house in the country. Maybe all the things you were in the middle of and couldn’t imagine leaving no longer exist. Maybe you are different now.

Build up your resources and give your future self as many options as you can. When your situation becomes clear, you’ll have the power to move forward.

See also: How to Make Progress When You’re Just a Dried-Out Husk of a Person