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Jennifer Dziura career advice Fridays on TheGrindstone and life coaching advice Tuesdays on our sister site, TheGloss.
Can you even remotely imagine yourself at 60?
Most people can’t. Maybe most 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 ladies.) 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 The skills and knowledge you gain will likely be outdated by then, but you’ll probably still be satisfied if you actually used the degree to build a career or business, or to make a great intellectual contribution.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 the Snow White evil queen!) 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 (and a line on a resume (see Bullish: Basing Your Career on a Resume is Like Competing in a Brothel Lineup), 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).
 | Bullish: 3 Career Mistakes Young Women Make (And How To Smash The Competition) |
 | Bullish: How to Sell Without Selling |
 | Bullish: Launching Your Empire While Your Youthful Mojo Is Sky-High |
49 days ago
[...] In any case, people sometimes ask me how I get so much done, or at least how I do so many things — for instance, see Bullish Life: A Day In The Life of Bullish (Caffeine, Pinstripe, and A Lack of Time-Wasting Bullshit). One answer: I’ve never looked back and regretted some span of time in which I did too many things and didn’t sleep and it was really hard. I don’t regret doing that in the 11th grade and consequently getting into a good college. I don’t see why I would regret doing it now so my forties and beyond will be backed by greater resources. (See Bullish: Extreme Advance Planning for Very Smart Women.) [...]
70 days ago
[...] your career, defining your values, reducing stress to help you move forward, and a healthy spate of extreme advance planning. And see last week’s Bullish: How to Be a Lone Unicorn for more on the value of doing hard, [...]
107 days ago
[...] the same spirit, Extreme Advance Planning for Very Smart Women is about strategic planning for your life. Serious motivation food for your [...]
183 days ago
[...] While you can’t predict exactly what your future self will be like or want, you certainly can set her up for success. See Bullish: Breaking Free From Terrible Situations and Bullish: Extreme Advance Planning for Very Smart Women. [...]
183 days ago
[...] While you can’t predict exactly what your future self will be like or want, you certainly can set her up for success. See Bullish: Breaking Free From Terrible Situations and Bullish: Extreme Advance Planning for Very Smart Women. [...]
Your ideal 60-year-old self sounds awesome! I think more old people need to wear ball gowns – they’re so dignified.
Slightly OT but at 60 I want to be like one of those awesome ladies that I served at the country club that just didn’t give a damn and could out-drink most of the men there.
196 days ago
[...] I think there will be more Bullish columns coming about the American lady-dream, or the idea of developing a portfolio representing a full and well-lived life (see Bullish: Extreme Advance Planning For Very Smart Women). [...]
Just curious Jen: Why specifically sons? I would have thought as an awesome lady you would be keen to pass those skills on to another lady, or at the very least not be worried either way. The specification of sons came as something of a surprise. Yes it was an assumption on my part, and I do remember what assumptions make of you and me, but I’m still curious.
Hi Oya,
Who knows why we want what we want? Actually, hmmn … my oft-quoted business muse regularly says, “Why have children? They’ll just rebel against you, no matter what you do. Why not just convert other people’s children to your side?” (My business muse runs an international arts organization and indeed has many young women who look up to her.) So, I kind of figured that, no matter what happens, there are already some young women out there whose achievements I can be proud of from a distance. (Even my teenage students are disproportionately female.) So, that’s kind of covered already. If I died tomorrow, I’d be happy with a few things. So, sons are more novel to me.
That said, sometimes we just want strange and particular things because that is the human condition.
Thanks for reading, Oya.
Sincerely,
Jen
Thank you. You make me question a lot of things about my life I take (lazily) for granted.
Printing this and putting it my book bag. Love your advice.
221 days ago
[...] professional online bible The Grindstone has another excellent Bullish advice column aboutadvance planning for very smart women. If you want serious, practical career advice of reaching your goals, this is the column to [...]