It’s normal human behavior to think “if only X happened, then everything would be so much better.”

In the startup world, these statements are usually around the next round of funding:

• fundraising/runway – if only I raised the A, then everything would be so much better
• winning a key contract – if only we had a fortune 500 client, then everything would be so much better
• growth and hiring – if only we had the CRO in place…

When you are a seed stage company, you think life would be so awesome if you only get to Series A and have more money in the bank. Before product market fit, you yearn for product market fit and imagine how amazing life would be (even though PMF is not permanent).

Much like in life, even when the desired outcome happens, it’s not so much better. Or maybe it is, but only for a brief period. Then we adjust to the new normal and our emotional status reverts back. And whatever that new normal is, it is not the “so much better” place we had imagined.

I appreciate that some of these desires touch on the existential. Closing the next round of funding seems to remove the existential risk you face. But… it really doesn’t. It just kicks the can down the road. X rounds of funding does not guarantee the X+1 round of funding.

The new normal is not awesome. It may not be so much better.

It is only different.

As you grow from 5 people to 15, it’s a very different world. From 15 to 100, even more different. The problems change, the challenges change, but it may always be existential.

This is the fact anyone in business has to get comfortable with. Large public companies have major challenges. Often existential challenges. Just look at Intel. There are public companies that are in “turnaround” mode, where things were going great—but then, for a whole bunch of reasons, they were not going great and it was existential. Now (usually new) management is trying to turn the company around.

When a startup is smaller, the existential risk is immediate. You can go from functioning to shut down in 30 days. For large public companies, the existential risk may span decades, but there are, in fact, public companies out there that are slowly dying. Just like great companies can lose their trajectory and mojo, companies can be turned around and made great again. It’s hard.

Nothing is ever easy. It’s always challenging. The scale and scope of challenges change, but challenges themselves never go away. It will never be calm and problem-free. Ever.

To paraphrase Sam Harris, dealing with the challenges *is* the living of life. The same is true of business. Business involves the constant dealing with new challenges. The sooner you learn to accept it, or even love it, the sooner it will be less painful and more just the norm. Because doing the difficult challenging stuff is what building and managing a business is all about.

It never gets easier. But your perspective changes. The fact that you love the challenge makes it hit differently. Perhaps it can even become… normal?

When I finally read this “Taste Is Eating Silicon Valley” post, it reminded me of some notes I had made a year ago under the heading of “Focus on the feeling.” A slightly different take on the same big-picture theme —>

When I watch a film, I focus on the feeling: how do all those elements come together to make the viewer feel?

Functionality (plot, dialogue, acting, costume, camera angles, lighting, locations) matters. But that’s table stakes. There’s a big difference between a synopsis that you could read on IMDb and a film that’s complete with the things that makes the story come alive.

The nuances of the execution of the film matter. It’s in the little details that define the character and the world, the scenes that release tension and make you laugh (even in a tragic story), and how the viewer is carried along on the journey.

A good film doesn’t have to twist your arm to carry you along.

During some films, I feel light, hopeful, filled with possibility. For the protagonist, and also about the world. After some films, the weight of the film stays with me. I leave thoughtful, aware, and perhaps a little sad.

Tech products can have the same effect. In 2013, I used HipChat to communicate internally. It was fine. It was functionally complete and did everything we needed it to do. And then Slack came out. The functionality of HipChat and Slack were so similar, and HipChat had an entrenched user base. Why, then, did Slack pull away and take the lead?

It was the choice of color, fonts, and interaction elements that created these “feelings.” When I tried Slack, it made me feel light, happy, less stressed. HipChat, in comparison, felt formal, almost stifling with blues and grays. There were also key product decisions on how you could start using Slack (easily), and onboard your colleagues (easily) that were heavy contributors. But, in order to even want to use it and get your colleagues to use it, you first had to fall in love with it. And love it enough to get everyone to move to a new platform. The feeling of joy and lightness was so significant that it caused mass adoption of Slack and mass abandonment of HipChat.

A good product doesn’t have to twist your arm to carry you along.

Same goes for the Apple Store vs. Best Buy. One draws me in, encourages me to be in my own bubble (even if the store is crowded), and look at and explore delightfully beautiful products. The other feels cluttered and overwhelming, even if it’s empty of visitors—and even if they’re also selling Macs and iPhones. Instead of products, I get to see aisle after aisle of boxes – a well-lit warehouse. Even the shelves – ugh – such a lack of care for the products they display. It’s an experience I avoid if I have a choice. These feelings of drawing in and repelling are a huge part of the design and care (or lack thereof) that each retailer has chosen.

Another example is Turo¹ versus airport-based car rentals. With Turo, you rent a car from a real car owner, you know exactly what the car will be, you meet the person who owns the car, and you have a warm, more-personal experience of delight for a car you actually want to drive. Turo focuses on the feeling, through the design of the customer experience from booking, to delivery, to the rules around having to clean the car (you don’t!), to return.

You want your customer feeling: That was awesome! Now I’m in a good mood. It makes me lean forward and want to do this again. Behind that feeling are the many careful decisions that make the process delightful.

In tech, there is a big difference between the functionality—”allowing users to communicate inside an organization”—and the details of how they do it, the feeling they get when they’re onboarded, the joy of a shared gif that gets the “room” laughing.

Focusing on the feeling is what will truly separate the winners.

1. Disclosure: I am an independent director on the board of Turo. ↩

There’s a lot they don’t tell you when you start film school.

They don’t tell you the percentage of film school students who end up directing their own feature (it’s <1%).

They don’t tell you how much directors make (usually <$80,000). Most directors, even cult idols like Todd Solondz, have to teach or work in another area to pay their bills.

They don’t tell you that the industry is teeming with gatekeepers, and there’s red tape everywhere.

They don’t tell you how much money you’ll need to make a real film, or that you need to be a very persuasive salesperson to raise that money—not to mention all the other skills you’ve got to have, including technical skills, teamwork, leadership, public speaking, and the ability to express a vision for something that doesn’t exist yet.

In the process, there will be times when your bank balance is in the single digits, you’re doing gig jobs to pay rent, you’re getting rejected every week and dealing with your hopes getting crushed, but having to persevere, perhaps getting sued over who owns an idea, and all manner of other setbacks. You want to share your stories, but you don’t want to be considered a whiner. You can’t complain to the rare friend who is doing well, and you can’t really talk to anyone not in the industry because they don’t get how hard it is. Your relationships can sometimes help you, but they’re likely to suffer while you (and maybe your partner) go through the rollercoaster. You’ll have to balance the projects you’re passionate about with the ones that will pay the bills. Most directors face countless obstacles and bumps during their careers that can easily topple a person.

Going in, everyone thinks: “I am the exception; I am the one.”

And here’s the contradiction — you have to think that. Beneath all the doubt and the bruises of survival, you have to truly believe that. And you have to hold on to that (at times) delusional self-belief if you’re going to have any chance at all of making it.

Same goes for startups. No one tells you:

• They don’t tell you the percentage of startups that actually succeed: <10%.
• Most entrepreneurs have to shut down their companies, lay off founding team members, shift their vision radically, or merge with a bigger company down the road.
• You’ll have to balance the mission you’re passionate about with the business model that pays the bills.
• The startup world, too, is full of gatekeepers and red tape.
• To build a real company, you need to be a persuasive salesperson, along with all the other skills you need to have, including technical skills, teamwork, leadership, public speaking, and the ability to express a vision for something that doesn’t exist yet.
• In the process, you’ll risk all manner of other setbacks, and on top of it all, most founders face countless obstacles and bumps during their careers that can easily take you down mentally.

But going in, everyone thinks they’ll be the one—and they should.

That’s the only way to stand a chance of succeeding. You have to believe you can navigate through the challenges, and at every turn, you have to make the right decision for the long term. And it is a long road, so you need your belief in your mission, combined with the ability to execute. You need the ability to survive a global pandemic and a complete turnaround in the venture market (forget growth at all costs, get those gross margins up, get to profitability). All the while still believing in yourself, believing that you are the one.

Advice is cheap.

The only way is to go off and be the one.

Small acts of connecting people can change someone’s life. In 2001, I experienced this firsthand when a friend at Microsoft made a quick introduction to someone at eBay. It led to a job that became a significant part of my life and career.

Since then, I’ve made it a point to help others in the same way. I’ve connected friends with potential hiring managers, people who work at educational institutions, and even dates ?. It’s easy to do, and it can make a meaningful difference in someone’s life.

Unfortunately, some people guard their relationships and even resort to games of “stealing” friends away from others. Lame!

Of course, there are caveats. I only connect people I know and trust, and I don’t bombard powerful connections with requests. But if I think an introduction would benefit both parties, I ask if they’d be open to it.

An abundance mindset in connecting people makes the world better.

One of the challenges of being an adult is wanting to do more things than you have time for. Maybe this is a challenge of being human?

Usually the urgent prevails over the important. I’ve tried to overcome this prioritization problem in many ways: doing things on the weekend, putting it in my to-do app, telling people about it for accountability, signing up with a tutor (hi Spanish).

Nothing has stuck. When there’s too much to do, it’s easy to ignore, delete, or cancel.

At the end of last year, the team at Ultraworking launched a new year resolutions challenge. They built a website specifically for this challenge called Last Resolution Standing, and the last day to sign up was Jan 1.

Everyone picked a resolution that could be done either:

• first thing in the morning, or
• 5 minutes a day

As a not-a-morning-person-at-all person, I chose 5 minutes a day. And I decided I wanted to revisit Economics. It was my undergrad major, but I felt I remembered nothing. So I got a PDF textbook and spent 5 minutes a day on it.

Fortunately, I did remember a lot of it—and today it seems like so much more fun than when I was actually studying it. And I’m now 5 chapters in, which is more progress than I thought I’d make with such a small time commitment.

Sadly, the Last Resolution Standing streak ended for me on the 19th (my first day at Sundance), and I’m not allowed to use the app anymore. I’m ranked 31st of 159 participants. Most people stopped quite early (Jan 13th is known as “Quitters Day” – the day by which most resolutions are done and dusted). But there are still 14 people in the running, which is really cool.

While I couldn’t use the challenge as a motivation, I could just re-start the habit. So I downloaded the Streaks app, and I’ve been continuing my 5 minutes a day of Econ reading.

Compared to everything else I’ve done, this feels really easy. I set a timer for 5 minutes either on my phone or on this cute timer I bought through their Kickstarter (what’s the point of a new habit if you can’t buy a little tchotchke?) and open up the textbook. There are times I get into it and have more time on my hands, so I just keep going. The lack of pain with this method is seriously amazing.

And the key is that I’m not obsessing about the streak. If I break it, great, I just continue the next day. I’ve found when I overdo things, the pendulum swings hard in the other direction.

I’m going to experiment. I’m sure this, too, will fall on the floor at some point. But my goal is to pick it back up quickly and continue. The goal is to keep it light and also easy to do (i.e. accessible any time you have the 5 minutes). That seems like the key.

Want to join me? Let me know what ritual you’re starting. And I’ll let you know how long I keep mine going.