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If you’re philosopher Lao-Tzu, the journey of a thousand miles begins with a single step. But if you’re Edith Harbaugh, it starts with a celeste Bianchi road bike — and the voyage is 3,360 miles. It begins in the Pacific Northwest, hugs the Canadian border, traverses national parks, cuts through the Great Allegheny Passage and ends at the steps of the Lincoln Memorial in Washington D.C. Such treks are laden with lessons, but Harbaugh didn’t expect how much her two-month, cross-country ride would inform how to build software and lead teams.

Harbaugh is the CEO and Co-founder of LaunchDarkly, a feature flag management platform. The startup enables engineering teams at companies — including clients such as CircleCI and AppDirect — to continuously deploy features at scale, as well as allowing business users to control code. Before starting LaunchDarkly, Harbaugh rose through the engineering and product management ranks at Vignette, Monster, Plantsense and TripIt. She’s also a contributing writer at ReadWrite and Co-host of the To Be Continuous Podcast.

In this exclusive interview, Harbaugh shares how her lessons from the road serve as tactics for both starting a company and effective software development. She shares techniques for grinding through the long stretches, making choices at forks in the road and cultivating a mindset that’ll give you enough to cross the finish line. Any founder or engineering leader seeking ways to equip and lead teams for the long haul will benefit from Harbaugh’s tips. Let’s get started.

Break rides into legs.

When Harbaugh decided to try her cross-country bike ride, she was hesitant. “I had read a lot of blogs and didn’t want to have the humiliation of getting two weeks into it, finding it miserable, quitting and then having it be a failure,” says Harbaugh. “But I knew I really wanted to see Glacier National Park. So I titled my riding journal ‘To The Glaciers.’ As soon as did that my mindset shifted. I thought, ‘Okay, that's about a two-week trip, that's a doable and worth it.’ Once I got to Glacier National Park, I paused to ask: ‘Am I still having fun?’ Ok, I’ll go another week across Montana.”

Harbaugh broke that week (and all those that followed) into days and each day into checkpoints: a gas station for milk for breakfast, a little diner for lunch and a Subway for dinner. “Each pit stop was about 40 miles apart. That allowed me to lock in my pace and arrival times. I knew I was on a cross-country trip, but only experienced the glorious and gritty of the ride in 40-mile segments,” she says. “When you build software, deconstruct a feature in the same way. Break it into smaller steps — or minimum components that help you keep your pace and schedule.”

This concept isn’t foreign to software teams, but what may be is what each component and checkpoint should entail. “I think there's a belief that software is just the raw code. It’s not! It’s everything that connects to it: the documentation, marketing collateral and more,” says Harbaugh. “Focus on just the raw code is the equivalent of just paying attention to my bike, like checking the tires at a pit stop or adjusting my mirrors as I ride. If I don’t pay attention to the overall health of my system: my fatigue, signalling to cars at intersections or reading the weather, I’m in trouble. This isn’t just a metaphor for running a company, but building software. It’s all very connected. If you build a feature and no one knows about it, that feature doesn’t exist.”

Software isn’t just code but all that touches the product. Just like each leg of a ride entails the bike and all it moves through.

Harbaugh isn’t advocating that everyone on the software team must code, market the product, sell it — do it all from soup to nuts. But they must consider it as the build to be effective. “The bottom line is that nothing pains an engineer more than to have worked hard on something that nobody uses," says Harbaugh. “But how do people know to use it? That’s marketing. ”

The same principle of “breaking big steps into smaller ones” applies to starting a company. “When I recruited my first engineer, he was hesitant. The company was pre-revenue and seemed risky,” says Harbaugh. “I told him we had enough money to pay him for a one-month-contract while I tried to fundraise. During the month, he could interview anywhere he wanted. After a month, he could either stay or take any of the permanent jobs he wanted. That gave him — and me — enough time to make a better call. He stayed on for the ride.”

Every ride starts with zero.

An integral part of Harbaugh’s philosophy — as cyclist, CEO and seasoned product owner — is that every ride starts with zero. She had an odometer on her bike, and every day, she’d reset it to zero. It helped her:

With cycling — as with product development — you win when you operate with focus, but you want to win when you sense progress.

At the beginning of LaunchDarkly, Harbaugh championed weekly sprints with daily stand-ups that includes not just engineering, but other functions like marketing and sales. “Each day, we talk about what we did yesterday. Then, we discuss what we're going to do today. It keeps a one- or two-year project from feeling daunting. I also find that it creates a great deal of pride and accountability,” says Harbaugh. “If you haven’t found your cadence for sprints at a startup, don’t fix the sprint durations in stone off the bat. I spoke with Kevin Henrikson, an engineering leader established two-week sprints, but soon changed them to be one week long. He noticed that all the work got done in the last 3 or 4 days of the two-week sprints.”

Edith Harbaugh

Write it down. You can always alter your route.

Harbaugh kept an online journal as she crossed the country by bike. “I knew this trip was something special, so of course I wanted to record what happened. I’d take photos and write entries throughout my months on the road,” says Harbaugh. “However, I realize now that I was also doing a daily stand-up — just solo. I was obsessively introspective about what was working and what wasn’t with my rides. I noticed quickly the difference between being tired and cranky, the latter which meant — nearly always — that I needed to eat. These are thoughts that many let pass, but when you write them down, you get to realizations and changes faster.”

At LaunchDarkly, each team has its task list that it uses as much as a to-do list as a capacity gauge. “As I said, we do a weekly sprint where we establish what we’re going to do — but before that, we review what we said we’d do. I try to set the tone that it’s fine if we don’t hit every mark, as long as we dig into why,” says Harbaugh. “The important aspect is writing it down. The mind just processes it differently when it’s written and team members can return to it asynchronously and as frequently as they want. Plus as a team, we can get a sense of if we are being too optimistic or not ambitious enough. Then we can adjust within a week.”

When new employees start at LaunchDarkly, Harbaugh tells them: at the end of your first week, you must publish a post on the company blog. “Try it out at your company. I tell them that they can write anything they want and we’ll edit it for grammar and spelling, but nothing else. It’s unfiltered and it’s fascinating,” she says. “Our ulterior motive is that we want to get a pulse of how people feel, how we’re doing and what they think of the culture. The public component is a big part of our content marketing strategy. Everybody in our company blogs — product, sales, ops, everyone. I want them to get in the rhythm of it. I ask the engineers to write an article once a month. It helps crystallize what they’re learning and is great marketing.”

You can't always A/B test the way forward.

From an early age, Harbaugh always liked riding bikes. As a teenager, she’d venture out 10 miles to the Washington Beltway near her home in Virginia. Soon it was 18 miles out to Reston, 24 miles out to Ashford and 30 miles to Leesburg, trying to get to the end of the 45 mile trail. “I wasn’t sure about 90 miles, so I asked my parents to drop me off at the end — 45 miles away — and biked one way back in,” says Harbaugh. “By 16 years old, I built up enough confidence and endurance to complete the entire 90-mile rides.”

The point is that it’s easier to test in some scenarios, than others. “If your primary focus is learning, test away. Think creatively as you are breaking projects into smaller tasks or organizing an experiment,” says Harbaugh.

But it’s different if you have a far-off destination you need to hit. On a cross-country ride — as in startup life — there are always diverging roads. “It was all forks — all forks. On any given day, there were so many decisions on the path forward. In some cases, like Montana, there was one road forward, but it was the exception, not the rule,” says Harborough. “In every state, I’d buy a paper map and scope out the best route. I wanted to avoid deserted roads and busy roads — both for reasons of safety. I looked for a road with a nice, wide shoulder and followed it. Sometimes that shoulder would peter out, and I’d have to make multiple course corrections.”

While Harbaugh could A/B test some parts of her journey — like which hotels gave her the best night’s sleep or gas stations had the best snack selection — she couldn’t with others. “If I were to hit my daily pace, each checkpoint for a meal and get to lodging by dusk, I couldn’t afford to double-back to take another road,” she says. “I did my best in the planning stage when I entered a state and pushed ahead. The key was to trust in your pattern recognition and then roll with the punches.”

Over Harbaugh’s career, this phenomenon has been most true with hiring. “You can't A/B test team composition. It’s not a helpful process to rerun a scenario of hiring a person. You can't. . That’s especially true with small teams at startups,” she says. “It’s about sample size. If you’re fine-tuning email marketing, you can do some complex A/B testing if you’re sending out 10,000 emails. You’ll never be able to hire — or interview — 10,000 people in a job cycle. I’ll paraphrase Jocelyn Goldstein:

You can’t A/B test your way to success. You have to find your guiding line.

You’re self-propelled and self-supported.

Ask any founder or sales lead or engineering head who’s accountable for building a company, customer base or app and the good ones point to themselves. The same goes for cycling. You’re your engine. It’s your two legs in rotation, propelling the bike and your body forward. That’s obvious, but here’s what Harbaugh learned from the road that helped her get better at that self-fueled forward motion:

You’re gonna need extra gears.

If you’re not on a fixed gear or one-speed bike, you’ve got additional gears — and you’ll need them. “Gears mean you’re more equipped to respond to the world around you. You’re a big part of what moves the bike forward, but the external — tailwinds, headwinds, the incline of the road — all matter. If you’re already running at top gear with no tolerance, you’re screwed if you need to pick up the pace,” says Harbaugh. “The same goes with projects. I know developers who say that a sprint will take four weeks, but say they’ll get it done in two weeks. You know what happens? It doesn't get done in two weeks and then your team's burnt out from trying. And there’s more ahead.”

Extra gears means having capacity to do more, not the requirement to do more. “The second biggest mistake I saw with failed cross-country rides was a guy who pre-booked all of his hotels on his trip. You’d think that it was liberating to have that structure, but he was in its service in the end. He was locked in. He could not fall behind. And, what’s worse, he couldn’t get ahead, as his hotel for the night had to be his endpoint that day,” says Harbaugh. “Extra gears is having the right tool to react to your environment versus being confined by it. In startup life, being equipped to be adjust and be nimble is more powerful than being accurate from the get go. It’d be nice if that happens, but there are just too many variables and contingencies that await.”

Take your rest days.

There are times when there were headwinds, packs of dogs chasing her bike or remnants of a tornado swirling near her. “Those days nothing really helps. We’ve all had those days — whether you’re part of a startup or not. The reason I could suck it up and go further is because I had rest days,” says Harbaugh. “If you research failed cross-country rides, the common thread of why people stop is usually fatigue. The guy who is hell bent on 200 miles every day.”

Harbaugh made herself take every seventh day off. “Even if I was in a town I didn't really like — which happened all the time — I stopped and took the day completely off. I did laundry, saw a movie, caught up on writing or read a book. But I didn’t bike,” says Harbaugh. “Taking that time off gave my mind and body rest and variety — and more so, an excitement to get back on the bike. Allocating and taking those conscious breaks keeps 8 hour-days turning into 12 hour-days, in which only 6 hours — if that — are getting work done. Rest days or hours help prevent that.”

A rest day doesn’t need to be the same day of the week or shared with others. “Some startups basically require employees to work on weekends — or prohibit them from doing so. When I’d ride, I learned which day — and environment — was going to give me the most rest,” says Harbaugh. “For example, I’d choose Sundays because I really liked sitting and working my way through Sunday’s New York Times. I also had my favorite fast food spot — Quizno’s — or hotel chain: Holiday Inn. That familiarity was as important as the amount of time I had to rest. I felt connected in new places.”

There’s never a bad day to ride.

After Harbaugh made it past Glacier National Park, she renamed her journal: “Never A Bad Day to Ride.” It reminded her that everybody has bad days and to keep riding because it gets better. “I hit some major bad patches. I remember when my phone died completely in Wisconsin. It was Friday night, so there’s a lot of drunk driving, and I’d just pass these white crosses dotting the road where people had been hit and killed. Not the most encouraging when you’re solo, approaching nightfall and without a working cell phone,” says Harbaugh. “I eventually found a bar with some rooms above it, but it wasn’t easy. But I still had fun that day. I think people often mistake a temporary bad patch for a permanent one. There’s a fire in production. One of your big customers is grumpy. But there are also the positive feedback on a feature or news of saving customers time in their day. Quite simply, have a channel in Slack or HipChat where you can expose and tally these moments for everyone.”

When you get a big victory, use it to fill everyone’s reservoir. “Keep people buoyed by really celebrating the successes. When LaunchDarkly got its first six-figure check, I called everybody in the conference room and I projected an image of the check up on the wall,” says Harbaugh. “I wanted everyone to not just hear how excited I was, but actually see the check and gather together, as the team that helped make it happen.”

Bringing it All Together

Harbaugh was an experienced technologist before she rode across the United States, but it’s that athletic feat that has given her tactics to build software and lead LaunchDarkly better. Among them: break jobs into smaller tasks. Every day starts with zero. Write it down — you can always alter your plan. You can’t A/B test everything. You’re gonna need extra gears. And take your rest days. Lastly, though there will be rough patches — there’s never a bad day to build.

“I remember the home stretch. I had just navigated a nightmare road in Pittsburgh with a narrow potholed shoulder that was hilly and shrouded in dense fog. When I got to town, most hotels were sold out due to a country music concert, so I had slim pickings. Although I was almost there, I wanted to quit,” says Harbaugh. “But I was three days out — it was the home stretch. I asked myself: ‘Can you do this for 72 hours more?’ I started thinking about the people who got me there. My sister, who had ridden cross country. My step-dad, who had taught me how to ride a bike. My dad, who had ridden 90 miles himself. My mother, who was waiting to ride the final five miles with me. That’s when you go from solo rider to peloton. From founder to startup. You get on the saddle, and you ride for yourself and others. That's how you can do anything of lasting value.”

Photography by Bonnie Rae Mills.

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