This is the fifth (and last!) in a series of posts about travel, work, and living on your own terms. You might want to start here: A Radically Different Life, You Are A Product: Defining Your Vision, You Are A Product: Core Values, and You Are A Product: Setting the Right Goals.

Let’s be real for a second: As a product person, you can plan Every. Single. Little. Piece. of your product until you wear your fingers out from typing, but there’s one small thing you can’t predict: Reality.

The more obsessive planners among us like to make sure every little detail and edge case is accounted for. Even if, by some miraculous stroke of fate, you manage to perfectly plan and execute your product strategy, there’s an almost certain chance that when you put your product out into the real world, in front of real users, they’ll find something you forgot.

But it’s OK. We’re not perfect so our products are never perfect. Sometimes you misinterpret the data. Sometimes a competitor beats you to the market and you have to go back to the drawing board because they thought of something you didn’t. Sometimes your brilliant idea turns out to be something only you loved.

This is why products pivot.

Humans? We adapt.

We all have some sort of vision of where we want our lives to go. Even if it’s a bit hazy, it’s something. We march toward it, every day making choices that will hopefully get us one step closer to where we want to go.

Then life throws a curve ball. Maybe some really interesting opportunity comes up that would also get you one step closer to your vision, but it’s a risk. Maybe the thing you planned to do took longer than expected and you’re running low on funds. Maybe external factors come to play and you have to pause what you’re doing to take care of it.

Things happen, we need to adapt.

I’ve had lots of grand plans. I’ve taken big risks that I thought would get me closer to my vision. Some of them failed miserably and often unexpectedly. I’ve gotten a lot better at dealing with these sudden changes over time, but in the beginning I thought everything was ruined. Something strange happened the more I “failed,” though. I got so much better at it. I got better at accepting it, dealing with it, and coming out on the other side having learned from what happened and ready to take on the next challenge.

I’ve taken a lot of risks, especially with my career. More times that I can count, the risks didn’t pan out the way I hoped they would. At this point in my life and career, I’m so comfortable with failure that, yes, it does sting, a lot, but I now know that I am perfectly capable of picking myself back up and figuring out what to do next. I take my moments to feel sad or disappointed or angry, but then I chalk it up to a minor hiccup and a huge learning experience on my path toward my vision. Onward.

There’s a fantastic article written recently by my former colleague and fellow product person, Frederique Dame. In it, there’s a section on failure. She talks about building a safety net and the idea that knowing “You’ll be fine if it doesn’t work out” unlocks a world of possibility. That’s the key to failing gracefully. Knowing that you’ll be able to figure it out.

Something awesome happens when you learn to fail gracefully. You become more willing to take risks. With great risk comes the chance of great failure, but you already know that you’ll be able to brush it off and come out even stronger, so really, unless it’s a life and death risk, it’s win/win.

You set loftier goals for yourself. You consider things you might not have considered before. You expect more of yourself. Your confidence grows. Your vision starts to seem so much more possible.

Dealing with “failures” that are out of your control is almost the easy part. Assessing your own progress according to your own guidelines is much tougher.

When you set goals for yourself and you don’t reach them, frustration grows and eventually you start wondering if you should just give up and find something new to focus on. And yes, sometimes that might be the best solution, but often it’s just the trough of sorrow.

In the product world, we set KPIs for our products — things we measure the product against to make sure it’s succeeding where we’d like it to. KPIs can be things like number of monthly active users, number of dollars transacted, number of new registrations — measurable metrics to help gauge not-so-measurable things like “success.”

At certain intervals (weekly, monthly, quarterly, yearly), we look at our metrics and stack them up against our KPIs to make sure things are on track. If something is working splendidly, we give ourselves a pat on the back and see where else we can apply that same process for an even bigger win. If something is off, we assess and regroup.

In some companies, retros and post-mortems are also a common practice. Once they reach a certain goal (or failure), they gather the working group to assess what happened, what they learned, and what they can improve for next time.

The same is true for Me: The Product. I tend to do my “reviews” when I complete a certain goal, when I feel like I’m failing at a certain goal, and always at the end of the year.

Because normal people don’t function in distinct quarters, I often set timeboxes for myself. I choose a certain amount of time from when I start on a particular goal. When that time comes, I assess how it’s going and make any adjustments necessary. Never before unless something is going extraordinarily wrong.

When I first started my consulting business (a big part of my vision), I knew I would be tempted by the promise of a consistent paycheck. To keep things on track, I set checkpoints for myself. “I’m 100% focused on building this business and won’t entertain any other job options until September. When September comes, I’ll assess what’s going on with my business and decide if I’m going to keep going.” When September rolled around, I looked at my spreadsheets (and my sanity) to see what progress I’d made in the company and, since it was going well, I set a new checkpoint: January. I did that until I felt comfortable that running my own business could keep the bills paid.

The trick is to set a checkpoint that allows you to free up your mind from thinking about how you’re doing every single day. That’s just stressful. And it means daily fluctuations can cloud the aggregate trend. Sometimes you need more granular checkpoints, just make sure you give yourself enough time to actually see results.

But what happens when things aren’t going well? It’s never fun.

Sometimes we pick the wrong goals. Sometimes we think something is right for us and it turns out it isn’t. I have friends who had dreamt about traveling solo. They had expectations of “finding” themselves or having some enlightening journey that brings out the person they always knew they were deep down inside but had to uncover.

Then they tried it for themselves and it turned out not to be what they expected. They hated traveling solo or they didn’t have the confidence to be alone in a new place. Or they just didn’t like sleeping in hotels or hostels or being in strange airports with delays and foreign languages. It’s easy to be fooled by the romanticized travel in movies and blogs and books.

Sometimes you have to try something to find out it’s not the right Something for you.

Does that mean you failed? I like to think not. I like to think you learned something new about yourself and you’re a stronger, better, more self-aware person because of it.

Slack, the tech world darling/unicorn, failed in its original vision. Slack started out as a gaming company. They were building a game called Glitch, which I played for a little while. They had this amazing vision for a beautiful game designed by all different artists. And it was beautiful. But it never took off.

I don’t know what happened first hand, but I imagine it went something like this: The brains of Glitch gathered and assessed their progress and realized that they might not have enough in the bank to get to their full vision. So they took stock of what resources they had at their disposal and realized they had something in their back pocket all along, but didn’t really acknowledge because it wasn’t a part of their original vision. That magic rabbit out of the hat was Slack. They’d built it as an internal communication tool and now it’s a beloved company worth billions. They didn’t fail. They learned. They took stock of what they had to offer. And they adapted.

(Fun fact: You can actually play a little Glitch on Slack’s 404 page.)

I broke the cycle of day-to-day short-sightedness in favor of long-term thinking and opportunities. — Me, 2013

When I started to think of myself as a “product,” I didn’t really have a plan for how I was going to go about implementing these ideas in my everyday life. I just took what I knew about building things for the internet and experimented on myself (and yes, there were some failed efforts). I certainly haven’t completely reached my vision yet, but I know from my experiences over the last few years that I now have the tools necessary to get there with time and diligence and a dash of luck.

The wonderful thing about this process is that it works at every level. It works for the CEO trying to figure out what their company should be and for the newly-minted product manager trying to figure out what their feature should do to meet the CEO’s vision. For us as individuals, it works for figuring out our own personal vision, all the way down to figuring out what our goals should be for the next week.

It works the first time you’re going through the process or the thousandth reset because you learned something new and need to recalibrate. That’s the thing about achieving a grand vision: Whether you’re a company building an awesome product or whether you’re just a normal, everyday person building your ideal life, it takes persistence. It takes guts. It takes a fair bit of confidence. And most importantly, it takes the ability break down big goals into smaller bites and to adapt to whatever gets thrown at you while staying true to your values and goals.

We can’t predict the future, but we can give our best effort to make our own future what we want it to be. We can always take the next best step forward with the information we have at the time. It might not be the perfect choice, it might not succeed, but you never end up back at square one. It’s always a win. Some way, some how, you’ve gained something.

In the end, with focus and persistence, always taking the next best step, you’ll get where you need to be.

I started this series by talking about how I’ve felt somehow foolish or like an outsider for not having the “typical” life and how lonely it could be at times. It took me about 3 years of trying, failing, trying again, and reminding myself that I don’t need to live the same life as everyone else to finally get to a place where I’m confident in what I’m doing and the choices I’ve made.

As I’ve met more people living and working toward their own ideal, radically different life, it has become less lonely and more realistic. My goal is to make living a radically different life something that’s totally normal for as many people as I can. Getting started can be intimidating, but I hope this series will help you fast-track through the first few years of that process and unlock the life you want to lead. I hope you’ll share your progress!

If you’re leading your own radically different life, or thinking about diving in to this world of crazy possibility, let me know if you’re interested in joining a Slack community to meet fellow “radicals.” I look forward to hearing about your vision and progress!

Thanks so much for following along in my first series! I’d appreciate a 💚 if it was at all helpful. And hey, why not share it with one of your favorite people? My next posts will likely be about some more travel-related topics, so please follow for updates!

(Special thanks to Jimelle, Kristen, Sam Hogg, Courtney Machi, and Kate Zasada for reading drafts and making me sound coherent over the last few weeks!)