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How to Think Outside the Box

Simple ways to get out of a rut (and into a new life)

“Think outside the box” is advice you often hear. But what if you’re STUCK in a box, a routine, a view of yourself or how others view you? Options for doing things differently may seem like too much effort (“That could be hard, and it might not work”) or just plain ludicrous (“That’s just not me!”). It can be easier to decorate your box and make it more comfortable than ever by sticking with what you know and calling it self-awareness. How many times have we said “I don’t do that,” end of discussion, thereby tying up the box with a bow?
"At last, a place where I am in charge!" my 9 yo daughter says inside her box.

I was a master box-builder. I did what I was competent at (career, family) and what I had to do (housework). Outside the box meant outside my comfort zone, which meant the possibility of failure, and as the child of Chinese immigrants, failure = falling into an endless black abyss, SO WHO THE HECK WANTED TO GO THERE?

But IN the box, was fear, restlessness, children who wanted to run free, and once I slowly let them, there was me yearning for something more. When I started Facing Forty Upside Down, I started with baby steps, learning to dive into a pool, to do a handstand, proving that I could be different than how I was. Then I wrote Some Nerve and faced many more fears, including the hardest ones for me: fear of failure, rejection, and pain. And most recently, I took on what I thought was an iron-clad box, a defining characteristic of mine – “I am not an athlete” – and pried it open with a year of hard training and became a triathlete ("What I Found at the Westchester Olympic Triathlon"). By going outside our comfort zone we create new comfort zones. And if we keep pushing the boundaries we never stop growing.

Here are some ways to think outside the box:

1) Go outside the box. And that doesn’t mean you have to go far. Draw the outline of your current daily life – your routine – and do something different this week. Go to a new neighborhood, introduce yourself to coworkers you don’t know, change your exercise regimen (or start one!). Decide that extra effort is worth it – get your bike tuned up, buy swim goggles that actually fit, get up early and go see the sunrise. If you feel resistance, that’s the box. It’s made of cardboard, push through.

2) Draw the outline of your life up until now – your upbringing, your personality, the characteristics that make you, you. And then challenge them. I thought “I’m a people person, not a techie person” until I started blogging (5 years after everyone else learned the platforms). If I hadn’t, I’d still be writing in a journal that no one else would have seen. “I’m not an athlete” was absolutely true…until I became an athlete in a year. What could you become this year?

3) Hang out with people who will challenge you, not just say you’re fine the way you are. I mean, you ARE fine the way you are, BUT if you feel like you want to shake things up, you’re not going to do that staying the same. There are many ways to do this for whatever excites (or scares!) you – join a club (like Toastmasters, for public speaking) or class or team (Team #SomeNerve on FB or Team in Training for endurance sports).

4. Go away with people who don’t know you – i.e. go on a retreat. This is a double whammy because you get outside your routine and outside the parameters of what people who know you think of you. Mommies don’t have to mother while on retreat, executives don’t have to be in charge. The “serious one” can relax and laugh as much as they want, the “follower” can float ingenious ideas they’d be too intimidated to at home. In my sad and anxious times, I found retreats healing escapes, in my healthy and vibrant times they’ve been a place to network and make friends. Every time, I come back a different version of myself, more in tune with how I want to be.

The best part of going outside the box are the people you meet and the fun you have – fun you never expected to have and experiences that will always stand out in your memory because you took a chance to get there. How will you step out today?

Note: Join me at the Women at Woodstock Retreat (Nov 6-8, Woodstock, NY) where I’ll be giving a keynote and workshop on living a bigger and braver life.


TEDxTalk "Warning: Leaving Comfort Zone. Things Could get Exciting."

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