How Long Is Too Long to Pursue a Goal? Deciding When to Quit or Keep Going

*Leaving Tongariro Crossing on the Te Araroa Trail, New Zealand 2018*

In 2018, I quit my job to hike across New Zealand, and people thought I was nuts.

At the time it was a stable, full-time career in Civil Engineering with benefits and a bright future. I would get sat down by people at work asking if I was sure and offers to stay for just “one more” opportunity. Concerned family members sent me job postings “just in case”…I had intentionally not wanted a job to push me home early. Friends would give me queer looks over dinners out when I talked about being excited about living out of a tent, and my concerned neighbors said they’d let me crash their couch when I returned when I let it slip once that I paid my car off in full to “ensure I have a roof over my head when I get home.”

But by 2018, all these well-meant people in my life were pushing against a goal that had been built up for so long, none of them could tumble it. A goal that started in 2009.

The Trail That Kept Calling: Discovering New Zealand’s Te Araroa

New Zealand’s Te Araroa Trail officially opened in 2011, but I had discovered it just a few years before when they announced its near completion. The trail felt personally built for me. My teenage self had an obsession with the Lord of the Rings and, between my love of the books and my family’s history in filmmaking, I would watch the special edition “how it was filmed” DVDs on repeat. When getting ready for school, when getting ready for bed. From concept to completion, but specifically, the destinations where they filmed. This historically highest winning Oscar trilogy was in New Zealand, and I wanted to walk where the fellowship had walked.

When I first discovered Te Araroa, it was still a relatively young and slightly feral 3,000-kilometer trail connecting Cape Reinga at the top of New Zealand to Bluff at the bottom. The route was designed to stitch together beaches, forests, mountains, farmland, city sidewalks, questionably safe stretches of highway, and even a river, the Whanganui, that you had to paddle. With plenty of mud, river crossings, and orange markers lighting the way, it was a hell of an adventure just waiting for me. The year I planned to go, I would be one of 1,200 people who attempted the “thru hike” or full route (less would finish), but it is attempted by nearly 2000 people each year as of today.

Also, 3000 kilometers is 1800 miles, or three pairs of Oboz Hiking shoes to wear through, just to give you an idea of measure…. and I wanted to take every. single. step.

How A Few Years Became a Decade: When a Goal Takes Longer Than Planned

So in 2009 I knew I wanted to do this. I thought it would be just a few years. Since the trail would open after I already had to report to my first military duty, I thought I would wait for my military service post college to be over. So… 2016? I would leave immediately when my time was up.

In 2013, they asked for volunteers to leave their commitment early! But I wasn’t financially ready and I wanted to explore my career more… so I decided to wait for 2016.

Then I had the opportunity to get my Masters affordably…which tacked on another year of waiting. 2017.

Then I went to EOD school… and didn’t finish because I got chronically ill. Had to wait another year. Spring 2018.

Then had to build in time to wait for the southern hemisphere hiking season plus save enough to pay for the extended storage and dog care for my absence to ensure I didn’t collect debts while hiking. I stayed at the job I didn’t quite like anymore to pay the bills… and delayed another four months. Late Fall 2018.

When Delaying a Goal Does Not Mean Giving Up

Then by November 2018, I was finally on the trail. Now I only had to walk approximately 4.3 million steps with 20-30 pounds of supplies on my back through tropical storms, shin splints, tendonitis, lost toenails, hip-deep mud, and a few (many) tears.

I was supposed to wait about 6 years, an already Huge length of time to achieve a goal in many people’s minds.

All in all I waited 9.5 years to cross the finish line in March 2019.

And suddenly the narrative of all those people that started this story were a whole new audience.

Suddenly, they thought it was cool that I had done such an amazing thing. People would say “I wish I could do that!” or “what a once in a lifetime opportunity!” No one faulted me for not having a job right when I got back, or renting a room from a friend for a few months to stay cheap. Frankly they didn’t care. Within a year, I had a normal job again and a normal home for myself and the dog that returned home. And we never had to sleep in the car (till three years later, but that’s another story).

Why People Change Their Minds After You Succeed

Enter The Psychology of Outcome Bias

There’s an actual explanation why people shift their positions on ideas and dreams they once criticized and its called the outcome bias.

Outcome Bias (thank you Wikipedia) is “an error made in evaluating the quality of a decision when the outcome of that decision is already known.”

This is different from hindsight bias, which distorts our memory in ways that favor the person with the bias. Think: your parents saying, “I was supportive of you going hiking the whole time! You’re just confusing that with parental concern” …that’s hindsight. And maybe a smidge of a gaslight.

Outcome bias is, instead, how we judge a decision based on how it resulted rather than the information available at the time the decision was made. One of the first researchers on Outcome Bias were Jonathan Baron and John C. Hershey. In their 1988 article “Outcome Bias in Decision Evaluation” for the Journal of Personality and Social Psychology.

They found that people rated identical decisions differently based on which resulted in a positive outcome. Once an uncertain decision proves successful, the risk, doubt, and disruption surrounding it can suddenly seem justified. The decision itself didn’t change, but the outcome changes the story people tell about whether it was a good one. Home purchases, pet adoptions, and online dating all come to mind. but so does New Zealand.

Before I completed the trail, people saw me leave a stable career, give up my home, and walk away without another job waiting. After I completed it, they saw courage, adventure, and an extraordinary accomplishment. They were evaluating the same decision. The difference was that they now knew how the story ended.

How Long Should You Keep Pursuing a Goal?

You see, a lot of people believe that there is a set time to achieve your goals. Life tells us when we should have the degree, the family, the “explore your options” time, the career set, etc. It’s all bullshit and yes we subscribe to it as if being successful is a specific metric to be measured. If you don’t reach that goal at a prescribe time, then you supposedly failed. That’s just not how life works! If you have a goal, it’s okay to say “not yet” and achieve on your timeline, but its only a “no” if you give up because someone else defines the when & how for you.

Once you achieve the goal, no one will ask how long it took you

They will just celebrate that you did.

If you’re interested in more on exploring this chat, I did a whole post about it HERE. Do me a favor and share it with someone you think needs to hear.