Bullish: Cultivating A Career When You Have Too Many Choices

Someone once Tweeted one of my columns – this one – with the note, “@jendziura says you can have anything you want, just not at the same time.”

I was baffled. I have never said that. I think Oprah said that. Or at least repeated it. I categorically reject that.

I mean, I recognize the fundamental truth that you can’t literally do everything at once.

I recognize that, if you work hard beginning at a young age, you can probably achieve your number one big goal – but maybe that’s it. Becoming an astronaut might be incompatible with having six kids. You can’t be President and also farm alpacas, although there’s plenty of time for both in a lifetime.

But I also believe in stretching the limits of what you can do at once, and not just via workaholism, although workaholism is a valid choice for certain seasons of life (see Bullish: Maybe Work-Life Balance Means You Should Work MORE).

Yet. Workaholism should be pursued cleverly, not just hard.

There are plenty of freelance gigs that it’s difficult to make a living at, but not too difficult to make half a living at. Why not do three of those – if you can use the same resources and blocks of work time to run those businesses, and especially if you can sell more than one of those products or services to the same clients, or to their friends and networks?

I believe in some high-level ADHD, and in stretching your capacity for managing multiple tracks of achievement, and for transmuting what most people experience as “stress” into a growth experience for getting what you want.

Let’s hear from a reader I’ll call Lenina Crowne, after the main female character in Brave New World and also a character played by Sandra Bullock in the 1993 film Demolition Man, which was very loosely based on Brave New World in a manner I found really cool when I was 15 but which didn’t at all distract my parents from enjoying a Sylvester Stallone film.

You’ve written many times on making ballsy life decisions, and looking at the worst-case scenario.

I have spent the last few years trying to figure out what my plan is for when I finish university (April 2013), and to be honest your columns have probably been the most convincing, helpful, and inspirational advice that I have found yet. But at the same time, you’re a smart woman and I know you don’t advocate making foolish decisions, starting an unprofitable business, or pursuing a dead end career.

I feel like I am getting closer to my decision about what I want to do, but I still can’t seem to come to a decision, because once I pick one, I feel like I am giving up my other options.

I know you have written about having your income come from multiple sources, but that doesn’t seem a viable option when you have no real work experience.

I know it’s difficult to say because you don’t know me, but I was wondering if you had an opinion on, or advice about having to decide on and commit to a job/ field.

When you were graduating, how did you decide on what you wanted to pursue? And is it possible to make a decision, but try to keep the other things you think you might want to do open as an opportunity one day?

Oh, choices, choices!

First of all: fuck, yes.

Yes, you can “make a decision, but try to keep the other things you think you might want to do open as an opportunity one day.” You can do this twenty-five times if you’re clever, and especially if those things have some tenuous sort of thread holding them together (and no more than one of them requires a Ph.D).

Let’s talk about how.

The paradox of choice.

Were you a young man in medieval times – and lucky enough not to be bound to the land – you might follow your father into the button-making guild, marry the woman your parents chose for you, and be a pretty happy guy, at least until the plague.

Now, you have more choices than probably anyone in the world. Really, I mean that – in Europe and most of the rest of the developed world, you get locked into a university track (or not) in the early teen years, once you’re admitted to university, you can’t try things out or switch your major, and once you’ve graduated, people kind of expect you to stick with whatever you studied. There’s very little of this going-back-to-get-a-second-masters-degree-at-35, for instance.

The problem with having too many choices is that there are so many roads not taken that even good outcomes are tinged with regret. (See Barry Schwartz’s TED talk, whence I stole this subtitle). I once spent three hours reading online reviews of rice cookers, and then, upon receiving my $20 rice cooker, wondering if I had made the right choice. If I had just gone to basically any store and purchased basically any rice cooker, I never would have thought twice about it. Does it make rice hot and less hard? Check!

Sometimes, any decision is better than no decision (well, most decisions are better than no decision).

And, in order to simply function in our brave new world, you just can’t think too much about those paths not taken. If you want to be in a relationship, you can’t preoccupy yourself with thinking about all the other men you could be with (or that you have been with and let go, or who are just like your boyfriend, but 20% better in every way!)

(See Bullish Life: Sometimes It’s Best Just Not to Think About It.)

Who says you have to commit?

“Life is short,” people say. What people? What are they talking about? Life is long. Very, very long, which is why Social Security is going bust.

If you live to be 80, you could have at least three fifteen-year-long careers. It is very well accepted in this country to switch careers or start your own business at any time, and these things are, in fact, even more expected of women, whose careers are often broken up by childbearing and childcare.

When I was a member of the National Association of Women Business Owners, I came to realize that more than half of the members were in their forties or fifties and had started their companies after their divorces.

Whatever field you go into first, aim to become an expert; what is your primary skill in one job can be a very valuable and unique side-skill in some other job.

Also, be sure to develop skills that will port from profession to profession: networking and social skills, making presentations, writing press releases, sales, marketing, being good with technology. Being an Excel goddess will always be a plus, whether you’re in fashion marketing or college football recruiting.

Some of these skills, you can get from whatever job you end up in first. Some of them might require a computer class here and there, or volunteering to do PR or event planning for a nonprofit.

In sum: become an expert in something – anything – as fast as you can. While you’re doing that, develop a penumbra of modern-economy skills that will work in any profession.

(See Bullish: Basing Your Career on a Resume Is Like Competing in a Brothel Lineup.)

Stay outside the 9-to-5 world…

…if you really don’t want to commit.

I have four different business cards. I’m not schizophrenic; I think I’m more free than most people.

I don’t know you at all, Lenina, and it may be possible that what you want to do can only be done within the corporate or academic worlds. So, maybe this doesn’t apply. But in the freelance world, you can switch careers anytime you like; you can take on any projects you want. In the corporate world, people get locked into structures that don’t benefit them. They talk about “lateral moves.” They say things like, “It’s hard to make the switch from marketing project manager to marketing manager.”

Ugh. Does any of that really create value? Such people are angling for the next tiny rung in some stratified corporate structure that exists to keep them in place, kissing someone’s ass for a two percent raise. How about, if you’re good at marketing, make the company you work for a shitload of money, and then they’ll either give you enough of it to make you happy, or you’ll easily be able to take your skills elsewhere.

If you do go 9-to-5 (understandable when you’re young and have student loans), keep in mind that the artsier the 9-to-5 job, the more likely coworkers are to understand your outside exploits. If you are in music marketing and also in a band, everyone understands that. If you work for an arts organization and feel an irrepressible need to express yourself (in exchange for money!) by screenprinting t-shirts or making furniture, cool.

However, if you work at Morgan Stanley and have, for instance, a blog that reviews local comedy shows, it is totally likely that someone will call you into his office and “suggest” that you take the blog down, or at least write it under a pseudonym. It is also possible that you will have an employment contract that specifically prohibits you from other employment or entrepreneurial ventures of any kind.

(See Bullish: Launching Your Empire While Your Youthful Mojo is Still Sky-High.)

When in doubt: mo’ money, fewer problems

I do recommend that you work your ass off, starting now.

(See Bullish: Using Your College Skills to Succeed After College and Bullish: How to Go To There.)

Whatever you did that got you into college was worth skipping parties and limiting Facebook time, right?

You can afford to suffer for the first few years. Just as hard work in your teens will redound to your twenties, so too will an aggressive launch benefit your future gentlewomanly self.

When in doubt about a next move, keep in mind that money, power, prestige, and fame (within any field) in your early ‘20s will open up your options in your late ‘20s.

So much later in life will depend on just being an impressive person, in general – at anything.

Personally, I have really benefitted from refusing to choose – I’ve always had multiple professions at once, and have danced from vocation to vocation.

Being interdisciplinary has benefitted me at every turn – as it turns out, everyone who wants an educational author wants one with standup comedy experience, and having been a Director of Marketing is quite helpful in marketing my educational comedy shows, and having an educational background (plus a short modeling resume) helped land me a place in a television pilot. Even people who are hiring for more sedate jobs generally like to think of themselves as pretty cool people in their spare time, so they tend to kind of like the fact that I’ve written some funny (and rather R-rated) bits on McSweeney’s.

In other words, anything you do really well isn’t going to hurt you. And anything awesome that other people are scared to do isn’t going to hurt you either.

If you’re not making mistakes, you’re not taking risks

Finally, allow me to free you to fuck up a bit! You wrote, “I know you don’t advocate making foolish decisions, starting an unprofitable business, or pursuing a dead end career.”

Okay, do stay away from dead-end careers. If you want financial independence by the time you’re forty, and to be able to work from a laptop on the beach, do not go into Human Resources.

But I’m not against starting businesses that aren’t guaranteed to be profitable. I’d rather see you try to launch a print-on-demand publishing company or an international bounty-hunting agency or a competitor to Facebook – and then fail and declare bankruptcy and drink for a few months and then try again – then see you slowly, slowly sell jewelry on Etsy. (See Bullish: Are You Thinking Too Small?)

Also, as I wrote in Bullish Life: How to Make Better Decisions, we always have to make decisions with incomplete information, and sometimes any decision is better than no decision. Please make any kind of foolish decision that doesn’t kill anyone and that you’ll at least be able to learn from.

When my first company failed, I was 23 and felt that everything I’d ever done in my life had been a waste. Everything – the high school debate championships, the AP classes, the philosophy degree! – had been poured into my internet marketing firm, from which I was now evicted, by order of the sheriff!

In retrospect, of course, it is clear that the personal attributes I poured into that company were not “used up” by the experience, and that – quite frankly – it really wasn’t all about me and making my life culminate in some sort of glorious poetic justice. Business should have fewer feelings in it.

In any case, I’ve made some pretty foolish decisions. Investors have to watch their money go down and up and down and up all the time in order to achieve serious gains. Same deal. Sometimes I meet people I would consider A Pretty Big Deal, and having been an entrepreneur – even a failed one – gets me into the club. In fact, in entrepreneurial circles, if you haven’t failed yet, you’re not even playing.

I think that’s true in general – if you haven’t failed, or you’re unwilling to, you’re not really in the game. Ballsiness and foolishness can look the same until you see how things shake out.

originally published on The Grindstone