Bullish: Extreme Advance Planning For Very Smart Women

Updated for 2022

Can you imagine yourself at 60?

Most young adults can’t. Many women especially can’t, since so much of our identities tend to be tied up in our appearances. (Not our fault, exactly: we didn’t make up the idea that attractiveness is really important for women.) But you’re totally going to be 60 someday, if you’re lucky.

Out of what you’re doing now, what will matter when you’re 60? If you start a company that grows into an empire or which you are later able to sell, that will matter a lot. If you write a book, there’s a good chance that that will matter a lot. If you get a degree, will you be really happy about that in 20-40 years? The skills and knowledge you gain will likely be outdated by then, but you’ll probably still be satisfied if you actually used the degree to build a career or business, or to make a great intellectual contribution. Will you be happy about having mentored someone else? Almost certainly.

If you’re in your twenties, it might be relatively easy to imagine your ideal thirties, in which you are a more awesome version of yourself, recognized by others for that awesomeness. But in your forties, fifties, and beyond?

Personally, my self-at-60 wants floor-length ballgowns with huge popped collars (like Maleficent!) and places to wear them, plus several strapping adult sons who, after recovering from their teen years, treat me in an admirably chivalrous manner, plus one gay son who really understands me. And a bunch of books I wrote when I was younger, so I can rest on my laurels and just receive letters (via telepathy-hologram-text) from people who enjoyed the books and are surprised at just how relevant they still are in 2039. And then I do some public speaking and answer questions insightfully, and then I get a lot of massages, and my managerial skills are so incomparable that my trusted employees run everything while I get the massages. This leaves me a lot of time to work out and impress people with how many pull-ups I can do. Also, there’s a beach.

There is absolutely no way this will ever happen on its own. If I keep doing exactly what I’m doing right now, I think I’ll be … okay. I can probably pull off the pullups, which will be part of why I look so good with white hair that matches my white suits. And I’ll be well-off enough to be able to obtain health care, and when I die, some people will say that I helped them. There will not necessarily be a business empire, books, admirable children, or a beach. Without some serious advance planning, I’m just a wrinklier version of myself (I already own the suits).


Do you want to be doing the same thing in five years?

Even if your life right now is pretty good, is that the life you want in five years?

If you want something dramatically different — or just to fit some travel in there somewhere — you will need to break out of what might even be a profitable and comfortable situation. If you are doing a job just for the money, or to move up in rank at doing the thing you’re doing right now, then you’re unlikely to end up anywhere very different from where you are now.

I have taken two entire months off from work and my life in New York — January 2009 and January 2011. Okay, well, I still did quite a lot of work, but it makes a difference whether you do that work in an office, in your desk chair, or in a cafe that keeps bringing you espresso and empanadas.

If you want to see the world from a bicycle, live an expat life in Berlin, or write a novel while experiencing Costa Rica, well, you’re unlikely to do any of those things at the time that you notice your lease is up in four months.

If you want to quit your job and start a company, well, some people do quit their jobs on a whim, but if you know you’re the sort of person who would sooner die a slow, painful, Prufrockian death — well, the time to plan is now. (See Bullish: Launching Your Empire While Your Youthful Mojo Is Sky-High and Bullish: What I Wish I Had Known When I Was 18).

Gifts from Brooklyn, Not Billionaires

People will sometimes agree to anything if you ask far enough in advance

So, how do you actually engage in extreme advance planning?

Map out a set of goals for 5, 10, 15, and 20 years — since hardly anyone really knows exactly what they want 20 years in the future, the goals can and should get more and more nebulous the further you go. For instance, “In 5 years, I’d like to be making six figures without killing myself” or “In five years, I’d like to have health insurance, no roommates, and run my own business while also keeping up my main job in my field” vs. “In 20 years, I’d like to be satisfied with having produced some good and lasting work, and have enough money and freedom to enjoy myself.”

The earlier you start setting things up for yourself, the easier it will be.

I have often quoted Daniel Gilbert’s Stumbling on Happiness (see Bullish Life: Breaking Free From Terrible Situations.)

Gilbert tells us that we often agree to things far in the future that we wouldn’t have agreed to closer to the present, because the brain anticipates rewards and consequences differently, depending on the time frame: when a friend asks you to attend her destination wedding in 18 months, it seems exciting and exotic, whereas if I asked you to come with me to Central Park tomorrow, it sounds like kind of a lot of hassle. In the far future, we think about generalities: fun, learning, excitement! In the near future, we think about logistics (ugh, airports) and opportunity cost (you’ll miss work, you could be spending the cash on something else).

If you want to spend part of your twenties living abroad, well, how about you leave in 18 months? That’s plenty of time to close up your local affairs, make your friends and family comfy with the idea (if you even care about that), set up work for yourself, and learn a foreign language.


Do you want to go abroad for six months and still have your job when you come back? Ask at least a year in advance. “I’d like to take six months off in 2024 — I’m flexible, whichever six months are best for you.”

Do your future plans just require more cash? If you’re in business for yourself and don’t feel you can raise your rates right now, schedule a rate increase for the future. What client can complain when you say, “My rates are going to be going up in April, 2024″? Then it seems as though the client is currently getting a sweet deal. You might even encourage your clients to hire you more now, while it’s “cheaper.”

If you are an employee, there’s sometimes a way to swing the same kind of thing. Most businesses are in such flux in a terrible economy that it’s sort of ridiculous to assume you’ll be in the same place in two years, but if you got friendly with a boss, there’s nothing wrong with a 25-year-old mentioning, “I need to find a way to be making $80,000 by the time I’m 28 or so.” This isn’t the same as demanding a raise right now (which may or may not also be a good idea) — if you phrase this right, it looks as though you’re looking for ways to add value and take on more responsibility so as to earn that increase. This could also be an entree to asking that boss how she moved to the next level in her own career.

Similarly, you probably shouldn’t tell your boss you’d rather be running your own company right now. But mentioning to your boss that you’d like to be an entrepreneur in the next ten years is totally reasonable without sounding too much like you’re going to leave them high and dry. Who knows, maybe that’ll be reason enough for your boss to rope you into starting up a new project or division — an intrapreneurial experience — or maybe you’ll ultimately be able to start a company that does business with your current company.

(See Bullish: When to Make Massive and Ballsy Life Changes for Your Career.)

One previous Bullish covered Three Career Mistakes Young Women Make, and I write all the time about raising the bar – working more in your twenties and early thirties, demanding more from your week.

You might find that putting this into practice requires sounding like a crazy person to less ambitious people. It might even require getting new friends, if the ones you have constantly discourage you from doing what’s smart: developing multiple income streams, or forcing yourself to network or maintain a professional newsletter in your off-hours when everyone else wants to chill. Or maybe you have great friends who are always there for you, but just don’t get what you’re doing. You have to make emotional silos: your friends are great, but so is your future self. She gets a timeslot too. Quite a few of them, ideally.

Your future awesomeness won’t happen by accident. You have to imagine the next level, and the next.

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