On my flight home from Christmas last year, I started thinking about what I wanted my New Year’s Resolution to be.

Most of us have some big, lofty life goals – a bucket list of sorts. But often the hustle and bustle of everyday life get in the way, and our day-to-day actions don’t align with the goals we set for ourselves. It can be hard to bridge that gap, and it takes conscious effort and a plan to keep yourself on track.

For me, I saw myself as an outdoorsman, but I knew that working behind a desk most days and only getting in a few short trips a year wasn’t getting me the experiences that I craved. So I decided to come up with a plan.

Objectives and Key Results

At the time, I was working at an ad-tech startup where we experimented with many different styles of project management. We were working on multiple projects at the same time with a small team, and had to make sure we were hitting our goals, and that things were getting done on time.

We had found success by organizing our efforts around the “Object and Key Results” system, or OKRs. An objective is some ambitious, qualitative achievement that you’re hoping to reach, and then the key results are a series of measurable, quantitative subgoals that help you measure your progress towards the objective. If you hit all of the key results, then you should be able to reach the objective.

Objectives and Key Results flow chart

The system is fairly well-known in the business world, famously used at Google, as well as Intel and LinkedIn. But it also struck me that it could apply well in my personal life, to help me reach ambitious lifestyle goals.

Setting an Objective

One of my personal goals was to be comfortable over long distances on the trail, even when carrying overnight gear. I wanted to know that I could hike on indefinitely, for hours and days at a time. I knew that if I set an objective of completing some long, scary sounding hike, it would set my confidence in my hiking ability for the rest of my life.

I remembered reading an article about backpacking 50 miles in a single weekend, and how it was a crowning achievement for any weekend warrior that wanted to push their limits in the backcountry. At the time, I had never hiked more than 10 miles in a day, and hiking the distance of two marathons sounded like something that was completely beyond my reach – 50 miles was more than half way across the state of Massachusetts, north to south!

It seemed like a perfectly ambitious goal, and so I started outlining the key results. I’d try to complete a 20 mile weekend by early summer, then a 30 mile weekend by mid summer. At that point, I’d see how I was feeling and whether I needed a 40 mile weekend, or if I could jump right to 50 miles.

I also set a key result of finding a list of friends who’d be interested in doing super long hikes. I knew that lots of people liked the idea of hiking a few hours a day, but it might prove tough to find people willing to put in 20+ mile days. I sorted the list into people I’d try to hike with for the shorter weekends, and the longer ones and started reaching out.

Working Towards the Key Results

Initially, I was nervous that these hikes might be too tough, but as the summer went on, it was fun to plan increasingly longer trips. I was building my stamina as well as my trail confidence – but more importantly, I was making measurable progress towards my objective of hiking 50 miles.

In preparation for each longer hike, I’d try to focus on things that went well during my last hike, as well as the things I could improve.

After one hike, I noticed my energy levels had crashed around midday because I hadn’t brought enough sugary snacks. After another, I felt there was a lot of gear I was carrying that I never really used, so I started to focus on cutting pack weight. I also started paying attention to my sleep habits on the trail – both with getting quality, restful sleep, and also adjusting to a “trail bed time,” just after the sun goes down.

Every time I’d complete a longer hike and check off a new key result, I learned a lot about myself as a backpacker, and what I’d need to do to keep pushing myself further.

Despite all of my preparation, I was still a bit anxious in the days leading up to my 50 mile weekend attempt. Was I really ready to hike 50 miles? It had seemed like such an audacious goal just a few months earlier, and now I was only a few days away from heading out into the woods for more than 20 hours of hiking. But when I thought back to all I learned, and all of the knowledge I’d picked up along the way, I knew that I was ready.

Working through each of the key results helped me reach my objective.

Planning Your Own Objectives and Key Results

If you’re worried that your life isn’t as adventurous as you want it to be, the OKR system can be a great way to make sure that your day-to-day actions more closely align with how you want your life to be.

Start by laying out some high level objectives. These can be subjective, qualitative things like being more comfortable in the woods or travelling more. Think of the kinds of things that you want to be able to point to and say “yeah, that’s me, I did that!”

Even if you only tackle one of these objectives every few years, they’ll still make for a great adventure road map for your life.

Once you have your objectives, go through each of them and try to enumerate 3 to 5 key results for each. These should be things that you can measure progress towards, or definitively check off once they’re completed. It could be something like “Takes 3 trips that are at least two nights out in the wilderness” or “travel to a new country every 6 months.” Something that’s more bite-sized and attainable, but that puts you on track to reach your objective. Make sure you setup deadlines and reminders to keep you moving forward.

A year ago I had never hiked more than 10 miles in a day and last weekend I hiked over 50 miles across 2 and a half days. Take some time to set a few adventure goals, and who knows what goals you’ll be able to reach!