You Can’t Get There From Here: A Few Stories About Backtracking

Problem: If you’re on the wrong path, no amount of tweaking or persevering will get you where you really want to go.  You’re headed down a dead end.

Solution: Backtrack until you’re in a familiar place, and try again. Repeat as necessary.


Life goes fast, and it’s easy for even the best laid plans to go off track. Sometimes you find yourself in situations you thought would treat you well, but your intuition lead you astray. Sometimes you just stop paying attention long enough to wander down a path you never meant to.

Whatever it is that gets you to the breaking point, in the end you’re faced with having to make one of three decisions:

  • Continue on because that’s what’s comfortable (easiest)
  • Throw in the towel and quit trying (easier)
  • Take a few steps back and try again from another angle (hard)

The first two rarely get you what what you want—if something’s broke, it usually doesn’t fix itself—but they’re easy choices because they’re comfortable. Backtracking, on the other hand, is a difficult choice. It’s uncomfortable because you’re not giving up… but you still feel like a failure. And you’re not staying the course… but you’re still aiming for the same goal.

Backtracking is a confusing, frustrating, and challenging experience. Of course, it’s also the only viable solution.

Those that take the challenge face serious trials, but the payoff is usually worth the effort. Those that avoid it jeopardize their own happiness and run the risk of never finding what they want.

To help you along the way, here are a few close, personal stories of backtracking gone right.

Mark and Nancy Start Over

Two of my close friends, Mark and Nancy, fell in love in high school. He was a wrestler; she was a cheerleader. They graduated and went away to school together. She studied literature, he studied psychology. Half-way through college, Mark proposed. Nancy, of course, accepted. They moved in together and got two cats.

When they graduated from college, they moved back home, got a house, got jobs, and added a dog to the family. Things seemed to be going well. Mark and Nancy were unstoppable—a true high school sweetheart story… or so we thought.

Somewhere along the way, Mark started to get violent. According to Nancy, it was never anything too out of hand—a push here, a kick there, a tackle on the carpet during a heated argument. Never anything that would leave a mark, at least not where we could see.

Of course, no one ever suspected a thing. We all knew Mark as the kind, silent guy. And he was the kind, silent guy… except, I guess, when he wasn’t.

Gradually, things got worse. Mark started to hit harder and he got angry more and more frequently. Even he realized there was something wrong and started seeing a doctor, but the bouts of violence didn’t stop.

What was Nancy to do? It’s easy to say she should have just left him, but things are rarely that simple when we’re in the middle of them. At this point, she’d shared more than 10 years of her life with Mark. She loved him. But where would they be if they kept this up?

After one particularly bad night, Nancy convinced Mark to admit himself to the hospital for the night. While he was away, she went to the courthouse, filed a restraining order, and changed the locks to the house.

The sheriff served Mark with the papers the next day. It didn’t go well. Just like that, ten years were gone. But what if she hadn’t done it? What if she’d just kept quiet and let things continue because that’s what was comfortable.

Would life have gotten better? Would she have been okay if they simply stayed the same? Would I still have a friend, Nancy? Hard to say, but the point is that she did the courageous thing and decided to make a change—to take a step back and try again. Now she’s free to start putting the pieces back together.

It won’t be easy, but it will happen.

So Close, Yet So Far Away

A few weeks ago, I drove out to Mt. Hood in NW Oregon with my sights set on the summit. It was a beautiful day, and I was ready to climb.

Though it’s the tallest mountain in Oregon, it isn’t that tall, and it’s more than 1,000 feet shorter than summits I’ve already climbed. No big deal, right? What Hood has going for it, though, is a challenging final 500 feet that are more technical than what I’m used to climbing.

As with any mountain, there are a number of different routes to the summit (queue clichéd life parable), but the shortest and fastest one is up a steep slope called the “Hogsback”—a trail no wider than your shoulders with several hundred feet of drop-off on either side. Once you cross it, you must maneuver through the Bergshrund, the final obstacle between you and the summit, which is a short maze of cornices—windblown snow outcroppings that will collapse if you make a bad step on one.

Of course, by the time you get to any of this, you’re already tired and just want to make it the last few hundred feet to the top.

So, I set out up the Hogsback. An hour later, I arrived near the top, only to find the Bergshrund impassable. It was too dangerous, especially climbing solo without ropes, and there was nothing to be done about it.

At this point, backtracking was inevitable. I’d either have to climb back down and head home disappointed, or somehow find the energy to climb down and take the longer, alternate route.

Neither option was ideal, but with the clear goal of reaching the summit, the choice was obvious—I’d have to muster the energy to carry on despite fatigue because there was simply no way to reach the goal from where I was standing. It added an extra two hours to an already tiring climb, but now that it’s done, I certainly don’t mind. In fact, I see it as two hours very well invested. The view from the summit was worth it.

A New Way to Sell Cupcakes

It was always Jessie’s dream to some day own her own business; she never did well working jobs where she was told what to do all day. So, even though starting a bakery was a stressful and challenging undertaking, the idea of supporting herself while doing something she loved propelled her forward.

She didn’t have much money at the beginning, so she started small, baking in her kitchen and selling at a local farmer’s market. After two years, she’d even worked her way into three more markets. Things were looking up, but it still wasn’t perfect. The markets were nice, but they couldn’t sustain the business, and they were seasonal, so even though times were good in the summer, they didn’t last.

In year three, Jessie was sure she’d finally get into the Portland Farmer’s Market, the most coveted and lucrative market in town. If she was accepted, she’d be set. She worked hard to put together a proposal the market board would like, and the future of the business was riding on their decision.

She was rejected. “Too many vendors returning from last year and not enough space” they said. She was devastated. But devastation wasn’t really an option. If the business was going to live, then something had to change.

Rather than give up, Jessie sat down and took a hard look at how her business operated and started to think of new ways she could make money. That’s when she learned about wholesaling. Rather than work tirelessly to make the food and then do it again to sell it, she learned she could sell it to stores and cafes that would do the selling for her. And that’s money that would be available year round.

She didn’t miss a beat. A few days later, she’d forgotten all about the farmer’s market that was surely missing out and hit the pavement meeting with store managers and coffee shop owner all around town. Just a few months later, she’s making wholesale deliveries almost every day.

She could have given up and lost the business. She could have stayed the course and gotten more unhappy each year, depending on some suit and tie to decide if she’d make enough money to live. Instead, she backtracked, took a second look at how her business could operate, and set sail on a new course.


As fun as it is to think otherwise, life, business, love, etc. cannot be programmed to “set it and forget it.” That concept, apparently, only applies to rotisserie chicken.

If you want to stay excited about life, you have to work to try new things and have new experiences. No matter how hard you try to automate your business or your work, it will eventually require your input and creativity to stay alive. If you want to build a deep relationship, you have to be willing to work at it. And when you do these things, they don’t always go right. As you’ve clearly seen, sometimes they go very, very wrong.

The only solution, of course, is to take a deep breath, re-imagine what you really want, and try again. Good luck.

Question for you: When have you had to backtrack? How did you get through it and was it worth it in the end?


For more on making big changes, read this piece over on Jonathan Fields’ blog. Image by: DrChumley1978