Travels in Plan B Nation: 3 years, 5 lessons

[Bint.3♥♪♫]

Last month—April 10, to be exact—marked the third anniversary of my exit from the salaried workforce and my entry into what I’ve taken to calling Plan B Nation. After four-plus years at Harvard Law School, where I’d handled speeches and other behind-the-scenes writing for then-Dean (now U.S. Supreme Court Justice) Elena Kagan, she decamped for Washington, D.C., and I decamped for parts unknown at the peak of the Great Recession.

It was, to put it diplomatically, not an easy time. The economy was in free fall, plus I had no idea what to do next. Which maybe wasn’t such a bad thing because, had I known what I wanted to do, I likely couldn’t have done it. (Did I mention the Great Recession?) Floundering in spring 2009 put me in excellent company. Yes, I was freaked out and unemployed, but I certainly wasn’t alone.

In recent weeks, I’ve been thinking a lot about the road I’ve traveled since those anxiety-ridden days and feeling a lot of compassion for the me who so stolidly trudged through them. I’ve also been thinking about what I’ve learned and what might be worth sharing. Here are five of the biggest lessons that I still carry with me.

1.  Transitions take a long time.  

I’ve written about this before, and it’s a really important point.  In New Pas­sages, best­selling author Gail Sheehy ball­parks two years as the min­i­mum time needed to sta­bi­lize fol­low­ing a lay­off or other “life accident.”  Five to seven years is common.  A related point: Transitions tend to meander—to be less like ladders and more like the classic labyrinth, where you wind your way slowly towards the center, almost arrive, and then suddenly find yourself on the outer rim, and then, just as unpredictably, back at the center again. I often find it helpful to remind myself that this is just the nature of the beast.     

2.  Sometimes the grass is greener because it’s greener.  

I put off leaving the Boston area for more than a year on the theory that wherever you go, there you are. Could moving to another place really make me happier? I’m happy to say that the answer is an unequivocal Yes. Indeed, I’d go so far as to say that moving to an area that I love is probably the single most important step I’ve taken to move my life forward.  In particular, moving to a place where I have a strong network of friends has made everything far easier—as well as a lot more fun.

3.  If you don’t know what to do for sure, start moving anyway.

Transitions, by their nature, generally involve a temporary loss of clear inner direction.  That was certainly the case for me: I was searching without really knowing what I was looking for (which, not surprisingly, made it really hard to find).

Looking back, one of the most useful things I did during this time was to take action even if nothing felt quite right—to experiment, try things out. That’s how I came (lackadaisically, glumly) to write my very first personal essay—which led to a blog on Huffington Post, which led to writing for Salon, which led to this blog, which led to writing for SecondAct (including Notes from Plan B Nation, my new monthly column), Psychology Today, and a bunch of other stuff, which, remarkably enough, actually does feel right and for which I feel really grateful.

And you don’t need to take my word for it: I’ve since come across similar advice in books by career guru Barbara Sher and LinkedIn co-founder Reid Hoffman. “You won’t encounter accidental good fortune—you won’t stumble on opportunities that rocket your career forward—if you’re lying in bed,” Hoffman writes in The Start-Up of You. “When you do something you stir the pot and introduce the possibility that seemingly random ideas, people, and places will collide and form new combinations and opportunities.” I couldn’t agree more.

4.  Be kind to yourself.

We’ve all heard a lot about mindfulness by now, but this quality doesn’t really get you very far unless it’s paired with self-compassion. Psychology professor Kristin Neff is a pioneering researcher on this topic, and her book Self Compassion: Stop Beating Yourself Up and Leave Insecurity Behind is geared to a popular audience and provides an excellent roadmap for further exploration.

5.  Let yourself be surprised.

The biggest difference between lucky and unlucky people may be that lucky people are open to seeing the unexpected. (For more on this, check out this reported research.)  Expanding your peripheral vision can do a lot to expand your opportunities.  I’ve found it to be useful—as well as fun—to consciously expect the unexpected. (Most recent example: I’m about to go off to look at a potential new home that I discovered last night on Facebook.)

Strangely enough, my Plan B Nation life has turned out to suit me far better than the life I had before. I’m finally doing work that feels both meaningful and creative. I have a great community in a place where I love living. The road I’ve traveled to get here was pretty remarkably hard, but that doesn’t tell me I did something wrong. It simply tells me that I’m human.

Another reason regrets are dumb

Chicken-regrets illustration

You’ve doubtless heard the maxim that “You don’t regret the things you do. You regret the things you don’t do.” I’ve never understood why so few are bothered by the major logical flaw here: You can’t do two things at once. Choose X? You can’t choose Y. Regardless of which path you choose, there’s something else you won’t be doing.

I think about this a lot when I’m questioning past choices or starting to second-guess decisions made months or years ago. More and more, I’m convinced that regrets aren’t signs of bad decision-making but rather reflections of temperament and cognitive style. Regrets don’t reflect objective truth. They’re simply interpretations.

A couple years back, I dipped a toe into the critical maelstrom surrounding the book Marry Him, writer Lori Gottlieb’s exhortation to younger women to marry that nice if slightly dull boyfriend instead of holding out for true love and risk ending up (like Gottlieb—and me) single at midlife.

Along the spectrum of Marry Him commentaries—which ranged from the virulently pro to the virulently anti—the review I wrote for the Chicago Tribune fell somewhere in the middle. While I certainly got where Gottlieb was coming from, I couldn’t buy her solution—and not because of its dubious politics but because I couldn’t see it working. (Indeed, with some dark humor, I couldn’t stop picturing a sea of future middle-aged women, cursing that stupid book that convinced them to marry the guy they’re divorcing.)

The fact is, life is risky. There are no guarantees, no fail-proof roadmaps to a fairy tale ending. The answer isn’t to blame ourselves or to look for ways to game the human condition but rather to do the best we can and accept our essential limitations.

I recently interviewed psychology professor Kristin Neff, a leading expert on self-compassion and author of a book by that name, and was struck by what she had to say on this topic: “We love to have an illusion of control because it makes us feel safe. In an ironic way, I think what happens when we criticize ourselves is that we’re saying ‘Oh, I should have had control.  If it was something I did, then I did have control, I just made the wrong move.’ When in fact, the reality is that I didn’t have a lot of control. I did my best, but I couldn’t make things turn out the way I wanted them to. In a weird way, sometimes it’s less scary to people to blame themselves than it is to admit that we human beings often don’t have a lot of say over our lives. It’s hard being human!”

My thoughts exactly.

The notion that our biggest regrets tend to stem from things we failed to do bears a striking resemblance to the maxim that “the grass is always greener on the other side”—the salient difference being that the two are invoked to make opposite points. Here again, I’m reminded of the 28 conflicting legal rules famously set forth in a 1950 law review piece. When judges go about inter­pret­ing laws, there are “cor­rect, unchal­lenge­able rules of ‘how to read’ which lead in hap­pily vari­ant direc­tions,” the author dryly concluded.

For her part, along with urging readers to make haste and marry, Gottlieb set out to do the same herself, albeit belatedly.  Her primary strategy: Be less picky. She expounds on academic research that places people in two relevant groups: “maximizers,” who demand the very best, and “satisficers,” who do fine with good enough. As Gottlieb sees it, the solution is clear. She just needs to switch teams.

It wasn’t until after my review was published that this thought occurred to me: Gottlieb has a beautiful child, a successful writing career. Wouldn’t a true satisficer start by focusing there?