Do it in jeans first

It was six months after my trek through the cloud forests of Peru when I learned I'm not supposed to hike in jeans.

At least it's what I was told, on a different mountain range and continent, by a Seattleite guide who volunteered to lead a group of hikers around the base of Mount Rainier in Washington.

So strong was his conviction that hiking should only be done in pants specifically designed and designated for hiking that he kept a spare pair in his Subaru — a car specifically designed and designated for taking oneself to the hike — and insisted I change out of my jeans and into those pants before we start.

Now, with over a decade of hiking experience, I know with certainty my pants had zero negative effects on those trips. On the contrary, there are great benefits to just going with the simple solution you have on hand:

• Start sooner, with less preparation or work
• Avoid committing too soon, when relevant experience is at its lowest
• Save money up front
• Avoid the sunk cost fallacy later
• Build grit and hone skills
• Build knowledge and experience to inform an upgrade, if there is one
• Leave room to enjoy and appreciate the eventual upgrade
• Still get enjoyment compared to not doing it at all
• Keep a growth mindset because there's no pressure to keep up appearances
• And my favorite: Keep things simple

And now, with over a decade of startup experience, I know there are loads of opportunities outside of hiking where first doing things "in jeans" is the better (yet non-obvious) choice.

For example, if you want to test a new way of talking about your product, you can do it with a handful of informal user interviews, a simple LinkedIn poll, a webinar with the messaging as its theme, or with the trial version of a simple testing tool like VWO. You don't need a six-month long branding project, an enterprise experimentation platform that would cost $100k+ and take months to implement, or a large-scale and expensive usability-testing solution... All of which were real suggestions people made and almost committed to before I intervened.

As another example, if you want to know how your customers use your product or where they get stuck in onboarding, just send them a one-line email or write a tweet. You don't need to hire a data engineer and shell out seven figures for a "modern data infrastructure stack" for this, as I've also seen people try to do.

To find the "jeans" for any new endeavor, look for a solution that's:

• Readily available, without requiring much time or money up front.
• Noncommittal, so you can upgrade when needed.
• Won't get in the way of your goals, so don't try wearing jeans to summit Mt Everest. If you're not sure what really matters or not, ask an expert.

Then, as you gain experience you can decide how to proceed, which you'll be able to do with more confidence, optionality, and likelihood to succeed. Whether that's hiring for the role, buying the enterprise product, committing to a six-month project, or filling the next decade with hiking trips including a return to Peru not in jeans but in your very own pair of pants — specially designed, designated, and purchased for the purpose.