I love talking about being “ballsy.”

Testicles are very delicate – very important, yes, but also very delicate. Like, say, eyeballs. Important, but quite fragile! Yet no one ever says “Eyeballs out, ladies! Let’s do this!”

So, when is it important to be ballsy? More specifically, when is it time to make massive life changes to get ahead?

There was once a time that I worried I was clinically depressed and would require medication I could not afford. After all, depression is a disease, right? It’s all chemicals in your brain? Clearly, sometimes, that is the case. It is especially not difficult to understand that the drastic hormonal changes related to pregnancy and childbirth might marinate a person’s cerebellum in liquid melancholia.

But, in my case, I was running a failing company in a dead-end town, I couldn’t pay my bills, I hadn’t had fun in (actual) years, my landlord was threatening to evict my startup, and I had cut out exercising and friendships in order to make more time to fail at things. So, I don’t think that was a case of my brain randomly deciding to make some depressing chemicals. I think that was a very rational reason to be bummed out.

It turned out that the “solution” was to give up on a solution: close up shop, admit that the only big, adult thing I’d ever done in my life was a failure, and move to New York with $400 and zero knowledge of urban living (Note: once, someone asked me to meet him on 34th St “outside the H&M,” and I checked every street corner looking for the subway entrance to the H and M trains, because I did not know that H&M was a store).

It all worked out, obviously. But it took much, much longer than I thought it would to regain my bearings, and massive life change is generally incredibly painful, or else sort of freeing in a deeply disorienting way, much like starting over in one of those post-apocalyptic movies in which everyone the main character knows is dead, but there’s no time to think about it, because avian-flu zombies are waging war over the world’s water supply.

Let’s talk about two situations in which massive life changes may be in order. (Note: TheGloss is a pretty young crowd, and accordingly, the below is aimed at relatively unattached young people. Do not abandon your children. Repeat: Do not abandon your children.)

Everything is bad, all at the same time

Is everything in your career and life so awful that you pick up motivational books at Barnes and Noble and laugh until you cry at how pathetically inadequate the advice is to your life?

This happened to me. The particular book was Julie Morgenstern’s Time Management from the Inside Out. There’s nothing really wrong with this book. It’s simple, general, and uncontroversial. As I remember it, Morgenstern pointed out that there are only so many hours in a day, and that it would be good to see them all at once on a calendar, and that most people greatly underestimate how long it will take to do a task; thus, you should try to estimate honestly the amount of time it will take to do the things you need to do, and then you should put these tasks on a calendar, scheduled for specific times. Well, yes. Few of us do this all the time, but it’s kind of hard to argue that that’s a good idea, right?

My response was to laugh hysterically and then tell Julie Morgenstern’s little cover photo, “That’s really cute for regular people, but IF I DON’T DO 500 THINGS BY TOMORROW, BY WHICH I MEAN SIX MONTHS AGO, MY LIFE WILL BE OVER!” There were also some expletives that Julie Morgenstern did not deserve.

If everything in your life is not working, all at the same time, it is actually fairly unlikely that incremental improvement will give you the results you want. If you have a terrible job in a terrible city where you live with a terrible boyfriend in too-close proximity to your terrible relatives, and you try to fix everything as it stands, it’s pretty likely that you will wear yourself out early on, and you will stop tinkering as soon as things become bearable again – that is, the goal will become relief, not awesomeness.

David Sedaris wrote in one of his books about going to Japan for several months in order to break his smoking habit; he just couldn’t do it at home, where everything is a physical cue to do the things one has always done. Dumping yourself in another country is an excellent way to make clear to yourself that there are many, many lives you could be living, and the one you’re failing at is not necessarily one you need to go back to and tinker with.

Drop everything. Go teach English in Moldova. Seriously, if you don’t have any money, you can still travel, because America is actually really expensive and a lot of other places are much less so. Just Google “vagabonding,” or try this to start.

Or, could you stop failing at something hard, go do something easy – maybe some kind of feel-good temporary job that allows you to pay your bills – while you use your newfound mental space to plot your next move? If you drop everything and take up dogwalking or coffee-serving, it won’t even look like a chink in your career at all if you can come out of it in a couple of years with a book, a new company, an invention, or some other creative enterprise most people aren’t ballsy enough to even attempt.

Things are good, but nothing is changing, and it’s hard to see how anything ever will

This is a more insidious life problem. It’s hard to let go of good things for great things. Plenty of people have this idea that they want to achieve some mystical, ultimate success and glory. (I was once in a diner with my vegan boyfriend, who was placing all kinds of special orders. The Japanese waitress said, in an unidiomatic way that I’ve remembered since: “Oh! You are vegetarian to the limit!”) If you have this idea that you want to take your career “to the limit,” but you’ve chosen a job (say, Human Resources manager) that can only be performed within the constraints of a fairly large company – and where glory is simply never awarded – then you’re going to have to rethink.

How many people have you known who had moderately comfortable lives, talked about breaking free and doing something riskier and more difficult but infinitely more awesome – and then they got engaged, and all you ever heard from them after that was stuff about different kinds of dresses and dishes?

So, don’t let that happen to you. (See Bullish: Maybe Work-Life Balance Means You Should Work MORE). For courage, think back to those last days of high school when everyone was really emotional and talked about staying in touch forever and how the best days of your lives were ending and blah blah blah and the senior class is giving this memorial object to the high school so its legacy will remain forever and it seemed so terribly painful to some people to move on. So … how did that work out? Does anyone want to go back to high school? (Dear god, I hope not.)

So, how many times since graduating from high school have you made a leap of the same magnitude? Is it time for one?

When my company was failing, I was paralyzed by fear. I woke up every morning terrified. I really did lose weight from stress (that’s not just a celeb excuse!), but I couldn’t afford new clothes, so I probably looked like I was going through chemo. I was constantly nauseated. I avoided everyone who might suggest that I do something I didn’t want to do, which was everyone with any common sense.

And then finally, one day, sitting in the beat-up car I couldn’t afford to repair (it had been hit by someone and I’d received insurance money, which I’d used to pay rent instead of fixing the hole in the bumper), with a stack of collections notices on the passenger seat, I had this fantasy of shaving my head and walking away barefoot – literally walking, right down the street of my neighborhood, and then into infinity – and I realized, “Seriously, what is the worst thing that’s going to happen here? I am not going to die, and I am not going to go to jail.” If you’re not going to die or go to jail, what are you worried about? In my case, embarrassment. That’s it. I was worried about a feeling.

If you are in either of the situations I’ve described above – everything sucks, or everything is just-okay with no upward movement – then try a little experiment. How about a mind map? (See last week’s Bullish: Pre-Internet Productivity Tips for more on the retro benefits of paper). Start with where you are now. Plot two paths: incremental improvement (i.e., fixing your current situation), and radical, shocking, temporarily painful life change towards something better. Plot what is likely to happen as a result of each path in six months, one year, five years, ten years. Add a little side-arrow for the worst-case scenario for each path.

You’ll probably find that the worst-case scenarios for both paths are about the same. I mean, you could die in Moldova, or you could die being hit by a car on your way home from a data-processing job in Albany. But seriously, worst-case scenarios are often, well … feelings, or else very remote risks that look silly when you write them down.

Is the chance of a worst-case scenario greater when you take a riskier path? Probably. (Although people get laid off from “safe,” boring jobs all the time.) But is there any chance at all that that safer path will lead to the awesome results that you want? Can you honestly plot that career progression on paper? Can you make a circle for what you’re doing right now, and one for the life you want, and connect them through any number of arrows? (For instance, if you want your own television show, and you currently work in marketing, can you draw some arrows and bubbles getting you from one place to the other? What’s in the bubbles?)

If not, what you’re doing isn’t “safe” at all. If there is no path from your current job or situation to where you want to be, you are doing the least safe thing there is: wasting years that you can never get back.

In retrospect, I’m glad my company failed, because even if it had succeeded, my life would not be as awesome as it is now. I’d still be in Virginia, for instance, and I wouldn’t be writing for TheGloss, and I probably would’ve tried hard to convince myself that a bunch of mediocre aspects of my life were just as good as the real thing in New York (did you ever know anyone who tried to tell you she was the “Carrie Bradshaw of Poughkeepsie”?) Not that I’m implying that everyone needs to move to New York. I’m sure there’s someone out there who wants to live on a ranch (the cowboy/cowgirl kind) and is trying to convince herself that caring for a dog, a bird, and two gerbils in her apartment is basically the same thing, because after all, who lives on a ranch? There’s no path on the mind map from here to there, unless you are willing to undergo temporary emotional pain, to risk embarrassment, and to feel very, very alone while you do things others regard as crazy.

I do like to giggle at the idea of being “ballsy,” but I think the real key to building the life and career you want is to be very unlike the most wobbly of male body parts: to be comfortable with the pain of dislocating yourself from the familiar. If you feel safe all the damn time, you’re going to get the same results as the average people all around you. Get cozy later, when you have grandchildren. For now, ruthlessly break away from futureless jobs, and cities, and people (repeat: do not abandon your children), and accept that momentary discomfort is the currency you must pay in order to move forward to untold levels of awesomeness.