12 Ways to Scare Yourself Silly in 2014

Eleanor Roosevelt once advised, “Do one thing every day that scares you.” I’ve always thought aiming for that daily was a bit much. Maybe once a week?

But courage is a muscle, a skill. I’m not a brave person by nature. I’m timid and prefer my routines. And, like most people I’ve met, I have to train myself to be courageous. So, every year, I try to push myself a little further out of my comfort zone. Here’s my list for 2014–12 things to tackle when you need a good dose of daring:

Travel—on your own. Go to a new city all on your own and spend a day walking the streets. If this isn’t a stretch for you, take a friend you’d like to know better but have been shy about contacting. You’ll come home buoyant with a sense of possibility.
Connect with a stranger. On the bus. At the café. In the grocery checkout line. Start a conversation with someone different from you. Particularly someone you can’t imagine having much in common with. A good conversation with a homeless person, a teen, or a retiree will change your world. I guarantee it.
Take a romantic leap of faith. If you’re single, ask someone on a date—someone you don’t think you have a chance with. Too pretty. Too brilliant. Too awesome. Who cares? Go for it. And if you have a special someone? Go out on a limb. Do something out of character—too sappy, too compromising. A week of love letters. A load of their laundry. Whatever it is you resist but suspect would amaze and charm your partner.
That thing that you’re afraid will make you weepy? Yeah. Do that. The movie you can’t watch because it reminds you of someone you lost. The place you can’t stand to visit because of the memories. When I was seven years old, my parents moved from one side of Washington to the other, and my mother lost her rose garden. She steadfastly refused to even drive down the old street and risk seeing the roses—alive, dead, absent. She didn’t want to know. But I always wished she had. Avoidance is no way to heal. Let yourself grieve.
Take a class in a subject that you secretly love. That’s right. No more secrets, people. Maybe you recite Hamlet’s “To be or not to be” speech to your bathroom mirror. Maybe you pore over Thai recipes on the internet but never actually dare to make one of the dishes. You can accomplish amazing things if you just stop hiding. My lineup for 2014: public speaking, salsa dancing, or acting. I’ll start with the one that terrifies me most.
Have a thought. Then say it. If self-censoring is your thing—like it is for me—watch for a situation where you really want to be honest. But worry about the reception. Maybe you’re afraid friends will think you’re a pussy if you point out that most human beings have an aversion to violence, despite what your television tells you. Maybe you worry your boss will resent you if you point out the downside of her policy proposal. Sure. Could be. Or maybe you will get a reputation for candor and insight. Dare to be honest when your conscience is at stake.
Go see your doctor about that thing that’s been bothering you. No matter how much you think you don’t want to know. You do. Trust me. The arthritis diagnosis was one of the best things that happened to me. Now I have a whole healthcare team and a load of options for coping with the pain and mobility issues. I wish I’d gone in two years earlier. You can’t do a damn thing about it until you face it. Your loved ones will thank you.
Track down that long-lost friend or teacher or relative you always wonder about. Hunt down their contact information. And then write a letter to someone you wish you hadn’t lost contact with. I’ve got a high school English teacher who changed my life. He’s getting up there in years, and I know if he bites the dust before I get a chance to thank him, I’ll always regret it. Maybe they’ll be angry or hurt or just plain confused. Who are you again? Or maybe your note will mean the world to them. You won’t know until you try.
Identify the thing you’re scared of that’s getting in your way. Then tame it. For me, this is totally swimming. With my arthritis worsening, the pool is my best option for aerobic fitness. So my fear of water has to go to the wayside. One step at a time. Identify one thing that’s limiting your health, professional, or personal goals. Then, knock it out of the park.
Where have you lost hope? Go there. We all go through dark times. But if your life matters to you, you’ve got to trudge on even when you’ve lost all faith in the destination. Maybe this means leaving your relationship. Maybe it means staying. Maybe it means switching careers. Maybe it means developing other areas in your life to fulfill you. Either way, it’s a scary, uncertain place to be. But one thing I’ve learned in a whole lot of darkness is that we have to find a way to go on, even when we think there’s no reason to. Especially then.
Develop a five-year plan for the one thing you’ve always dreamed of—but have put off. Whether this means living abroad, writing a memoir, or buying a house, you’ve got to map a very specific route to your dream year by year, month by month. Give yourself a Plan A and then a Plan B and even a Plan C. Tell yourself one way or another, you will get there. Maybe you’re afraid you don’t have it in you. Maybe you’re afraid you do—and then what new responsibilities would you have to tackle? Who cares? Do it anyway. Chart that route to your destination and follow it.
Befriend that person who unsettles you. You know who I’m talking about. We all have that one person who challenges our status quo. Our assumptions about ourselves and the world. That one person who throws us back into gray space just when we think we’ve got everything mapped out in black and white. Too bad. Suck it up. Instead of shoving this person back to a comfortable distance, ask him or her open-ended questions. And actually listen. Really listen. Don’t turn it into a debate. Just try to understand. Be curious. Open up to another worldview, another experience that is radically different from your own.