10 Life-Changing Lessons I Learned from Jason Fried

#10. Bury the hustle

Sergey Faldin
Feb 21 · 9 min read
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Jason Fried. Image source.

Jason Fried is the founder of Basecamp, a Chicago-based technology company. He is also the co-author of Rework and It Doesn’t Have to Be Crazy at Work. His company’s blog, Signal v. Noise is read by more than 100,000 people every month.

Jason works no more than 40 hours per week, has many hobbies and is happy. Is he successful? I think so. But if we asked him, he wouldn’t give a damn.

He is one of my heroes, and here are the ten lessons I learned from him.

#1. Don’t set goals

“The reason that most of us are unhappy most of the time is that we set our goals not for the person we’re going to be when we reach them, but we set our goals for the person we are when we set them.” — Jim Coudal

In today’s “hustle”-culture, goals are everywhere. You set goals for your diet, your weight, the amount of money you make, when you become a millionaire (25? 30? 35?) and how much your business should grow this year.

All of this doesn’t do good to our anxiety levels.

Whenever you set a goal (or any plan), you feel obligated to complete it. If you don’t, you feel terrible. Guilty. Stressed. Why do that to yourself?

Jason (along with his partner, David), say “fuck it” to goals.

As he told Inc. Magazine, “We don’t have big, long-term plans, because they’re scary — and they’re usually wrong. Making massive decisions keeps people up at night — I don’t like to make those”.

Instead of setting goals and treating your life as a bus ride, where you go from station to station, Jason views his life and career continuously.

He writes in his blog:

“I was 16 or something like that at the time. I didn’t have a goal to make two logos, or to be able to charge $5000 for a logo. I just made logos. And then I made software. And then I made web sites. And now I make software again. No goals in the process that I remember.”

#2. Stop trying to win “it all”

“We are going to win!” — says the ambitious entrepreneur in Silicon Valley. “Winning” became a go-to verb when describing business success.

But what exactly are we trying to win? Who are we trying to beat? What game are we playing?

“We’re trying to win the competition” — ok, so you want to start a company and “win” everybody else in that space. Does this mean you get 100% of the market? 80%?

Winning everybody at everything is a huge expectation (or goal) to set. Chances are, you won’t live up to it, and be stressed as a result.

Jason reminds us that we don’t have to win at everything:

“Build something good, keep your costs low, keep your growth in check, hold back your expectations, find some customers, charge them money for your good/services, make more than you spend, and you’ll buy yourself another day, or week, or month, or year in business. Just aim to stay open, don’t aim to win anything from anyone. Staying afloat is a win for yourself.”

#3. Have JOMO (Joy-Of-Missing-Out)

I remember moderating a panel with a famous Russian entrepreneur, who said something like, “I build this business because I had so much FOMO. Everybody around me was doing something, while I felt like missing out on life…” and everybody started to applaud.

There is a lot of talk about FOMO these days. If you don’t follow the news, you’re missing out. If you don’t buy the new iPhone, you’re missing out.

But what will happen, if you do miss out on a thing or two? Would you die? Probably not.

Instead of having FOMO, embrace what Jason calls in his book, It Doesn’t Have to Be Crazy at Work, JOMO: the Joy Of Missing Out.

Jason and his team at Basecamp constantly ask themselves, “What makes sense, for us? What works, for us?” and as a result lead the life they want.

They have never raised money — and finances their company by bootstrapping and reinvesting profits. They never had an office in San-Francisco, they’re based in Chicago (although they famously pay Silicon Valley salaries). And they are intentionally keeping their company small (55 people) and distributed — with employees all over the world.

By missing out on what’s conventional in the industry, Jason and his team have the option to do whatever they want.

One piece of advice I gave out to new Medium authors that people liked was, “don’t read others”. I meant you shouldn’t allow influences, trends, and “what works” influence your writing. You should spend time finding your voice.

In the interview with Chase Jarvis, Jason says: “I skip most influences that I don’t want”.

Live your life. Embrace JOMO.

#4. Seek out unactionable advice

If you look at most self-help articles on Medium and various blogs online, you’ll see that most of them are filled with practical tips and actionable steps. Sometimes they even have headlines like, “3 Simple Steps You Need To Take” or “1 Hack That Will Change Your Life”, etc., etc.

To me, this sounds a bit hypocritical. That’s why I never read articles like that.

Nobody can ever know how I should act, or what you should do — because they don’t know our particular situation. They don’t understand our context. The best way for a self-help author to write a good article is to share their particular story. Say what worked for them. Maybe that will inspire us in one way or another.

When people accused Jason of being too “high-level” in his books and not giving actionable advice, he wrote:

Most actionable advice isn’t advice at all, it’s opinion. Sure, you can give someone advice by giving them your opinion, but when you stitch actionable to the front of advice, it masquerades as fact. But it ain’t.

The key to obtaining the most value from self-help articles is to bring your mind — and your situation — to understand what your actionable steps can be.

“Seek out unactionable advice. You’ll figure more out,” says Jason.

#5. Find a mentor one step ahead

One question I get often from people is, “What gives me the right to teach others what I know?”, to which I reply: you don’t need to be Tony Robbins to talk about life, or to teach others. You just need to be one step ahead.

Jason on this:

If you’re starting a brand new business, talk to someone who started theirs a year ago. Or if you’re about to sign your first office lease, talk to someone who just signed theirs. Or if you’re about to hire your first employee, get advice from someone with a two-person company, not 200. I think there’s a good chance the advice will be more helpful.

Not only that you can teach others if you’re one step ahead, but you should learn from people who are close to you.

Twenty-year olds spend a lot of time watching YouTube videos where people 3 times their age advise on how to become successful. But people usually give advice based on their particular context, at the moment. Everybody is talking to themselves about themselves all the time. Hence, the advice from a 60-year-old won’t be as relevant to someone who has just graduated from college.

Seek advice from people who are one step ahead of you. And teach people who are one step behind.

One of my favorite quotes from Jason: “Yes, history has much to teach us, but history also has much to trick us. Last week is a better predictor of this week than the last decade would be.”

#6. Busy is the new stupid

At Basecamp, nobody knows where everybody else is. There is no (in Jason’s words) “presence prison” of the green dot in Skype or Slack or any other app you use for work communication.

What matters is, “Are you getting the work done?”, not how many hours you’ve spent working, or whether you’re “Available” (read: open for interruption).

This is, probably, the best and least practiced aspect of how Basecamp works. No shared calendars. No green dot. No immediate status meetings. No office (!). They work, they gut stuff done, that’s it. In Jason’s words, “Time isn’t a commodity we trade. No one can turn your day into theirs.”

In many companies, “showing that you’re working” is often confused with work. You get from your employees what you incentivize them to do. When you ask people to show you how much they’ve worked, they’ll fake it (change the clock on their computer or whatever).

As Warren Buffet says, “Busy is the new stupid”. Don’t be busy. Be productive.

#7. Break projects into smaller projects

I get my best work done when I feel excited. That’s why I so impatient when it comes to new projects. I know that if I sit on it for too long, the excitement might wear off and the project would feel like, you know, work.

I bet that’s true for you as well.

Jason’s company uses project cycles that last 6 weeks or less. They understand that short time horizons keep it fresh and that a long project will more likely to be completed if it’s broken into small little projects.

If you want to get something done, make sure you stay excited. To do that, break your project into smaller ones, create those “small wins” for yourself.

#8. Give it five minutes

“The faster you react, the less you think. Not always, but often,” writes Jason on his blog. What he means by that is that often we want to put our ideas, our opinions out there. We disagree impulsively and don’t give the new thought or concept room to sit and sink in.

How many times have you been reading a book and said, “Oh, I disagree with this”?

When you give something five minutes, you’re less likely to act as a hothead and disagree with everything on the spot. If it took a person years to write that book and make an argument, what makes you think that you can just brush it as wrong on the spot?

Whenever you feel like you’re about to disagree with a new idea, stop. Give it five minutes. Maybe you’ll change your mind once you understand it better.

#9. Don’t call yourself an entrepreneur

With so much hype around startups and entrepreneurship, everyone is an entrepreneur. People look at examples like Elon Musk or Jeff Bezos and think they should be like them.

But entrepreneurship doesn’t have to be crazy or intimidating. The core message of Jason’s book Rework is that it’s noble and great to start a small side business to supplement your income.

I find this idea liberating.

You don’t have to reach for the stars. Contrary to common wisdom, it’s OK to set reachable expectations.

The idea of Jason’s book is that you don’t go and raise millions of dollars for an idea. You don’t rent an office. You don’t hire experts. And you don’t build in advance. Instead, you solve a particular problem with less and scale slowly, if you have to.

You don’t call yourself an entrepreneur. You go and solve a problem and build something people want — and become one.

#10. Bury the hustle

This lesson doesn’t come from Jason particularly, I read it from his partner David, on their blog. But it sits at the epicenter of the Basecamp’s core values, and I believe it’s important to talk about it.

You don’t need to hustle today to survive. And people who brag about 16-hour workdays, well, they just brag. You wouldn’t hear a person who has to work 3 jobs to make ends meet brag about it.

But the “hustle” culture is pernicious because it makes everybody who doesn’t subscribe to the grind feel left out. It makes them feel “not enough”, hustle became the new norm.

In their blog with Jason, David writes, “The truth is you’re going to die, and it’ll be sooner rather than later, the more feverishly you devote your existence to the hustle and its grind. Life is tragically short that way.”

To me, “bury the hustle” pretty much sums up the whole philosophy of Basecamp, David, Jason, and their books.

You say NO to more dumb shit (like meetings, raising money for an idea, spending a lot of other people’s money, etc.) to be able to say YES to things that matter.

You ask yourself all the time, “What works for me?” instead of copying what somebody else is doing.

If more people lived their lives and led their companies like Jason and David, maybe we’d have more happiness in the world.

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Sergey Faldin

Written by

Writer. Making sense of the world and teaching others. | Daily creative newsletter: https://honestcreative.substack.com/ / faldin.sergey@gmail.com

The Startup

Medium's largest active publication, followed by +731K people. Follow to join our community.

Sergey Faldin

Written by

Writer. Making sense of the world and teaching others. | Daily creative newsletter: https://honestcreative.substack.com/ / faldin.sergey@gmail.com

The Startup

Medium's largest active publication, followed by +731K people. Follow to join our community.

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