Jason Fried doesn’t set goals “because they’re mostly artificial. You either hit the goal and you’re happy [or] you don’t hit it and you’re upset. And if you hit it, then you just set up another one. What’s the point?” His conversation with Amy Elisa Jackson in this episode is filled with wise advice that comes from his direct experience as the CEO of a successful company, Basecamp, and co-author of Rework, a New York Times bestseller about work.
He believes in the power of saying “no” and the freedom it brings. “What I found is the more often I say ‘yes’, the more often I regretted the decision down the road. It’s really easy to say ‘yes’ to something, especially when it’s later on because it doesn’t cost you anything right now. No is just more specific, and it frees you up. You end up having more flexibility and more independence when you say no more frequently.”
Jason has been a TED speaker. In addition to Rework, he’s been the co-author of It Doesn’t Have to be Crazy at Work, and Remote: Office Not Required. In this episode, you’ll also learn how to keep your work hours under control, be happier when you are working, and how parenthood can teach lessons you can use at work.
Click to listen now. Listen and subscribe on Apple Podcasts or wherever you get your podcasts. Through honest and candid conversations, guests share how they navigate their careers through achievements, hurdles and heartbreaks encountered along the way. If you have a question or feedback for us, message us on Twitter (@glassdoor using the hashtag #InPursuitPod).
Amy Elisa Jackson: Welcome to IN PURSUIT, the podcast from Glassdoor. I’m your host, Amy Elisa Jackson. In every episode we share the real stories of extraordinary people navigating life’s most pivotal moments at the intersection of the personal and professional. Today we’re talking to the author of, It Doesn’t Have to Be Crazy at Work, Jason Fried. He’s the co founder and CEO of Basecamp. He’s a prairie restoration hobbyist, a dad, a husband, and a huge believer in saying no. This is one conversation I’m super pumped to have, so let’s jump into it. Jason Fried, welcome to in pursuit.
Jason Fried: Thanks for having me on.
Amy Elisa Jackson: Jason, when you think about your career, what has really surprised you the most about it?
Jason Fried: Probably that I look at it as a continuation. I look at it as one job. I feel like I’ve had one job since I’ve been 14 or something like that. I don’t look at the things I’ve done as separate things. They happened at separate times and they kind of happened, of course, with separate people. But it’s always been the same thing for me, which is just try to do the best work I can in whatever it is that I’m doing and try to be fair to people that I work with. That’s kind of it. And then, of course, the things are different, but the fundamental principles are the same.
Amy Elisa Jackson: So if careers aren’t sort of this linear thing and it’s kind of a continuation, what’s really been your best detour or your best pivot moment?
Jason Fried: It was probably when I decided to start this business that I run now called Basecamp back in 1999, because before that I’d had other jobs and I worked on my own as a freelancer, and then I hooked up with two other people in ’99 to start this business. So it was the first time I’d ever had a partner in a business. Everything else had just been myself. So that was kind of the moment when I feel like I was able to do more than I could simply do on my own.
And that sort of led to where we are today. It’s funny too, cause my dad always told me never to have partners in businesses, and I’ve always had great partners. I’ve had different partners, but I’ve had great partners. They’ve all been great. And so while I usually trust my dad, I think he was wrong on this one.
Amy Elisa Jackson: It’s interesting because so many people say that partnership can go awry or it can sort of go left very easily. And you’ve written books with partners, you started companies with partners. What is it that has surprised you the most about sort of having a partner in the hustle or a partner in creating a business?
Jason Fried: Yeah, it definitely can go wrong for sure. I think the key is that you have to agree on, let’s call it, 85 to 90% of things. You don’t want to agree on everything because then you don’t need two people and you don’t want to be constantly butting heads. So I think that I’ve been surprised by the ratio, which is 85 to 90% of the time times, we agree. And then the 10% we don’t, we can battle over that and the decision ends up, I think, being better.
And what I’ve seen a lot or happen a lot now is that new founders feel like they need to have a partner until they go out and seek one out specifically, and they just kind of find someone with a different set of skills they have and they’re like, “Okay, well you have this and I have that, so now we’re partners. Let’s start this business together.” And I don’t think that’s the best way to do it.
Amy Elisa Jackson: It seems like a lot of times these days people do try and go out and find someone who has the skillset that they don’t have. It’s almost like trying to date someone and you’re just trying to find a perfect fit or a perfect match. What has it been like to sort of have a friend or have a friendship and relationship with your partner? Any advice for when things go wrong? Because it can go left and then all of a sudden, you’re on the outs with a good friend or someone you’ve known for years. How do you navigate that?
Jason Fried: Yeah, that’s a really good question, and I should probably clarify that I wasn’t really personal friends with these people. I was kind of professional friends and then we’d work together on things prior to going into business together. I’m not sure it’s a good idea to go into business with a personal friend. It can work certainly, but I haven’t had that experience. I feel like it’s best to be sort of professional friends, which is to know what they’re good at and know what you’re good at and to really know, to have worked together, not just to have read someone’s resume or heard something that someone’s done, but to actually work together on a day-to-day basis on a particular project so you can see how well you mesh and if your values are lined up or not and what previous disagreements look like.
Were they easy to handle, or with someone extremely stubborn? Are you extremely stubborn? What are the things that could cause this to go awry, and be good to know that upfront before you sign up. So I think that that’s really important.
Amy Elisa Jackson: Absolutely. One of the things that I appreciate in reading your books and sort of listening to your podcast is really your outlook on saying no and ruthlessly prioritizing. So you don’t set goals. So then, what does your decision-making process kind of look like either personally or professionally? If you don’t set goals, how are you making calls in your day-to-day life?
Jason Fried: Yeah, so the reason I don’t set goals is because they’re mostly artificial, and you either hit the goal and you’re happy, you don’t hit it and you’re upset. And if you hit it, then you just set up another one. It’s like kind of what’s the point? I think the key is to just do the best you can. You shouldn’t need a goal to do the best you can, and hopefully, you’re going to do the best you can anyway.
I used to jog a lot more than I do today, but when I used to jog, I remember there were some times when I wanted to hit a certain time, like I want to run a six-minute mile or something. And you go out and you run, and then you end up running a 6.07 or something. And technically, I remember being upset about that. I’m like, “I didn’t get the six-minute mile that I was going for.” But that’s the wrong question to ask. The right question is, “Did I enjoy the run? Did I get some fresh air? Do I feel like I exercised?” Those are the questions to ask.
So when it comes to work it’s very similar. It’s not about, do we hit this target, or do we have this number of people sign up? That was just made up numbers. It’s, did we enjoy the process? Would I want to do it again this way? Was it creatively challenging? Was it fun? Did I like the people I worked with? Did I like the decisions we were making along the way? Did we learn something? Those are the things that are more important to me. And so if the answer’s no to most of those things, like are we going to learn something new with this project? No? Mmm. Less interesting to do. Am I going to enjoy this process? No. Less interesting to do. Do I like to work with these people? Yes, no, whatever it is. Yes, more interesting to do, or no, less interesting to do. It’s more about the process and the outcome there than it is hitting targets. So that’s why I don’t like setting goals.
Amy Elisa Jackson: When in your life was the moment, if you can remember, when you harnessed the power of no, when you really like came to this understanding and this awareness of sort of, that you can’t do everything? Because I feel like that would probably be a very pivotal moment in one’s life to realize the power of no and it is okay to say no.
Jason Fried: I think it wasn’t really a moment. It was more of a culmination of many, many moments, or many episodes, and primarily because what I found is the more often I say yes, the more often I regretted the decision down the road. It’s really easy to say yes to something, especially when it’s later on, because it doesn’t cost you anything right now. You’re like, “Yeah, I’ll do that. Yeah, I will do that yet. Yeah.” And then you get around to doing it, and you’re like, “Oh, I wish I didn’t say yes to that. I’ve got another idea now. It’s been seven months. I want to do this instead, but now I can’t because I’ve committed to that.” I think it’s that. It’s that feeling of, yes later that’s really the dangerous version of yes. And I think just realizing that over and over made me recognize that no is just more specific and that it frees you up. It makes … You end up having more flexibility and more independence when you say no more frequently.
Amy Elisa Jackson: I love that. I’m personally trying to learn how to say no to more in my life, not just my personal life, but also professionally. How have you sort of shifted that notion at least at Basecamp around, it’s not a bad thing to say no.
Jason Fried: Yeah, and by the way, I agree, it is hard to do and I’m still working on it. There are certain things I still say yes to that I wish I didn’t or there are opportunities that I take on that I go, “Eh, maybe I shouldn’t have done that.” But that’s fine. I’m not perfect and I’m not going to be perfect at this. It’s just a matter of, hopefully, I’m more on the side of right then I’m not overtime when it comes to these sorts of things. I think the way to do it is, at Basecamp, everyone is pretty much dedicated to the work that they’re doing and they’re not really often pulled away from it by other events. So I think in a lot of office settings and a lot of companies, people are constantly being pulled off their work to do something else. They’re being pulled away.
So they’re told to do this project, but then there’s some other thing that comes up and someone else changed their mind and they’re pulled off the other thing and they’ve shifted to this other thing. And then it becomes this culture of yes all the time, because you’re changing all the time. We’re pretty much focused, let’s call it six weeks at a time, on the work that we need to do. And during that time, unless there’s an emergency, you’re focused on that work and you’re expected to say no to everything else. Like you’re supposed to say no to everything else. That’s the whole idea.
Amy Elisa Jackson: So tell me what part of your personal life has most impacted your professional life in the past year?
Jason Fried: Over the last year, and it’s called over the last five years, I have two kids, one four and a half and one 10 months. And that’s the biggest impact. That’s been the biggest impact, because it sort of forced me to remember how much time I have at work and how much time I need to stay away from work and how important sleep is and all these other things that come up in life when you have other real serious responsibilities. And I think it made me a better manager of my own time and someone who’s more protective of time away from work and also time at night to sleep.
Amy Elisa Jackson: And so how much sleep do you get?
Jason Fried: Eight hours. I aim for eight, typically get between seven and a half and eight and a half depending on the nights. Which means, right now my son is getting up at 5:00 in the morning, which means I have to go to bed at 8:00, 8:30 sometimes in order to get the right amount of sleep. If I stay up till 11:00, I’m screwed. It’s just not going to happen. And then I’m messed up. So my wife and I kind of go to bed based on the kids’ schedules, not on when we want to go to bed. That way I can get a full night’s sleep and -be a good husband and be a good father and be a good coworker and be a good boss and be a good business owner. Cause if I’m on six hours of sleep, I can’t be any of those things.
Amy Elisa Jackson: Wow. Even just the two-hour difference really affects you?
Jason Fried: I think it might even be something like 12 minutes less sleep has a measurable impact on cognition, on speed, on a number of different things. So it really does matter. And for people who are like, “I can get by on five or six hours,” it’s like, you can get by terribly. You’re not going to die yet, but you’re not really anywhere close to what you’re capable of, and you’re actually hurting yourself. And that’s not to say, sometimes I get six because of something that happens or I don’t get to bed until late or I’m reading a book and I’m kind of absorbed or the kid gets up early. I’m not a perfect sleeper by any means, but I really recognize how important it is to try to get there, and I’m really careful about it.
Amy Elisa Jackson: It’s interesting because I read Arianna Huffington’s book, which is all about the sleep revolution and her focus on sleep. It’s interesting because how we’re juxtaposing that with sort of this hustle culture. What is your thought on how you balance those two popular trends right now?
Jason Fried: Yeah. I’m not a fan at all of the hustle grind culture. I think it sends a terrible message. I think it forms the wrong habits. I think it’s unsustainable over the long term. And I think a big part of it is because people are busier than they’ve ever been, but it’s not that they’re getting more work done, they’re just busier. We’re more distracted these days. So for me, my workday is eight hours. That’s it. I don’t need to work longer than that because I have a full eight hours essentially to myself everyday to do the work I need to do. And that’s plenty of time. And I was reminded of this recently. We wrote about this in our book, but I had this experience recently where I was flying. My family went over to Amsterdam for three weeks and we were flying from Chicago to Amsterdam direct.
It’s about eight hours, the flight, and you’re on this plane and you look at your watch and you’re like, “We’re probably close to being there, right?” And you’re like, “Oh no, it’s only been four hours.” And you look at your watch again and it’s like, “Oh my God, now it’s been five hours and 15 minutes.” And then you look at it again, it’s only six now. And you realize like eight hours is an incredibly long amount of time. It’s a long time. It’s plenty of time to do a great amount of work well, and then stop. So this idea that you have to hustle and work 10, 12, 14 hour days, I don’t understand it. And first of all, you can’t do it well. There’s diminishing returns after about eight anyway. And you’re probably also not sleeping very well, so you’re in this manic mode of denial where you think you’re just kicking ass, but you’re absolutely not.
Amy Elisa Jackson: How can people detox from the hustle culture? Because I feel like it’s almost like a drug. You kind of become addicted and it’s a cycle that you kind of can’t get out of. Any tips on detoxing from hustle?
Jason Fried: Yeah, it is a drug. It is addictive, which is why so many people do it and keep doing it. I think a good thing is to maybe keep very good track of let’s say three … Let’s make it a week. Every week, keep extremely good track of the time you’re putting into things and then look back on that the following week and go, “Were those good days? Why was I bouncing?” My guess is that you’re going to find that you’re bouncing around between all sorts of things all day long, and meetings and phone calls and meetings and phone calls, and 15 minutes here and 15 minutes there.
I think sometimes you have to step back and look and see, because if you’re just in the zone and doing it all the time, you don’t really realize how messy it probably is. I think what you’ll see is that your time is a mess and then you can start to figure out, how can I group these things? So maybe if I’m going to have a bunch of phone calls, let me do them in succession and over two hours in the morning and then stop. So I’m not doing them 15 minutes here and 10 minutes there and 15 minutes there and another 20 minutes there, breaking up my day into smaller and smaller chunks, which makes me less and less efficient.
The other thing I would do is encourage you to take some vacations and get the hell away from work for a while. If you find yourself unable to leave work, you’ve got a problem. Now it’s, again, a little bit different if you’re on your own and only on your own. Then if you’re away then your business shuts down. But that’s probably okay too. And probably very healthy for 10 days or two weeks here and there. So I would encourage people just to get a little bit of perspective and get away from work. And then when you come back you might see things a little bit differently.
But if you’re in the middle of it all the time, hustling all the time and you feel like, if I leave, everything’s going to … that the world’s going to end, you’re also a little bit too self-important, and things are going to be just fine without you typically. So I go through those experiences, keeping track of your time, looking at it, and then trying to group it better. And then also just staying away from work for a while and getting some perspective away.
Amy Elisa Jackson: Jason, you seem like you’ve got it all together. Eight hours of sleep, eight hours at work. So tell me, when’s the last time fatherhood knocked you on your ass?
Jason Fried: <laughter> All the time. By the way, I don’t have it all together. I try to have it all together. I am very imperfect in all of these realms, but fatherhood’s definitely kicked me in the ass many times. The thing I’ve learned though from it all, which applies to adults as well, is that you simply can’t make someone do something they don’t want to do. And if you’re trying to get a four-year-old to put their shoes on and they’re just not going to do it, you can’t … I mean, you could force them to do it, but that’s not going to help anyone.
So that’s always been a good reminder. But it’s always hard to remember that in the moment when your patience is thin and there’s just no momentum on it in a certain direction and you need to be somewhere. Those are the things that are really difficult. But those are really also good moments to just go, “You know what? I can’t make this human being do this thing they want to do, so hey, maybe I’ll just bring the shoes along with us in the car and just to … And then we’ll put them on later.” It’s just a good moment to figure out how to deal versus how to break a stalemate and figure out a compromise and get around that.
Amy Elisa Jackson: I feel like parenthood is the thing that can truly humble you, slow you down and show you who’s really in charge.
Jason Fried: It’s very, very true. It’s extremely true, and it’s cool because it changes. My son’s four and a half now, and he’s going through all sorts of different things than he went through when he was three, and we have to change our perspective on things all the time, so. And then we have a 10-month-old, so we’re going to go through it again in a different way. It is a very good reminder of how out of control you actually are in a sense, and then realizing the things you’re actually truly in control of, which is really only primarily your reaction to things. It’s not the things that are happening, but it’s how you react to those things that are happening.
Amy Elisa Jackson: So there’s a trend of people taking these workplace productivity tools, including Basecamp, and applying them to their home and family lives, trying to bring some order to the project of managing a family. Would employing Basecamp at home be a horrible idea?
Jason Fried: There’s a number of people who do that. In fact, people who work here often do that. I don’t think it’s a bad idea. I think though, of course, you have to be realistic about, if you assign a task to somebody at work, it’s kind of like, well that’s sort of what you pay them to do. If you assign a task to your wife or your husband or your partner or your kid, eh, it may not be received that well. So I think it’s really important not to be a taskmaster at home. And some of these tools kind of put you in that mindset. But I think as far as communicating and being thoughtful about sharing schedules and talking about what needs to happen and making decisions together, that’s very valuable.
Amy Elisa Jackson: Is it your love of writing, the prairie lands, vintage watches, and having hobbies that sort of keeps you from over-investing in work?
Jason Fried: I’ve always been interested in a variety of things, but I think it’s the fact that work ends for me at around 5:00, that now I have time to do other things. I think a lot of people who work too long, they simply just don’t have time, which means they don’t … They can’t develop hobbies and other interests. It’s impossible. The people I know who just spend all the time at work and thinking about work and, they’re not healthy and happy people most of the time. Because work’s hard sometimes and challenging and you don’t want to have that on your mind all the time. You need to get away so you can come back to it with fresh eyes and a fresh mind and feel rested.
Amy Elisa Jackson: But that’s easy to say as a CEO of one of the best companies. Is it feasible for the average person who clocks in and clocks out to ascribe to some of these anti-hustle life theories? You’re already at the top of the pop, if you will. It’s kind of easy to say it.
Jason Fried: Well, that’s very generous of you, by the way, and thank you for that. But I don’t think … I mean yeah, certainly we’re all … We can only do what our environment essentially allows us to do. So if I work somewhere, if I was an employee somewhere, and it was hustle, hustle, hustle, hustle, hustle, it’d be very hard. But the thing is is that, like you said, I’m the CEO of this company, but there’s lots of CEOs of lots of companies who are technically more successful than us that are working in 90, 100, 120 hour weeks. So it’s not about reaching a point where you can do this. It’s about making a decision to do this. Now, because to your point though about people who don’t have control over the way or the place they work or the way that place works, I think what’s important is just recognizing what you are in control of.
So for example, if you don’t like being interrupted all day long by your coworkers, then maybe you shouldn’t interrupt them. Maybe you can control that. Maybe you can control, next time you have a question, maybe you can look it up yourself versus trying to ask someone for that answer. Try to be the change you wish to see, and have a little bit of influence. You just got to figure out what influence you have and what you can control and what you’re in control of and do the best you can. It’s, of course, unfair of me to suggest that somebody who doesn’t have control over the way a company works to try and change that company. It’s just probably not going to happen. But you might be able to change yourself, change a single coworker, change a small team that you’re on. That’s the kind of change you should start with and then see where that goes from there.
Amy Elisa Jackson: What’s been the biggest obstacle to making Basecamp a calm company? Have you had to fire people or take drastic actions to keep things calm?
Jason Fried: I think it’s just always a challenge, because we have a lot of really creative people here and creative people want to create and they want to do stuff and some people have a tendency to work more than they should perhaps. And so I think just reminding people and reminding ourselves that hopefully it’s not just lip service, that we believe in this and that eight hours is plenty of time during the day, and 40 hours is plenty of time during the week. And sometimes we’ll spot people who are putting in time over the weekends or something like that, and we’ll just gently remind them that that’s not necessary, that they don’t need to do that, that anything that’s happening on Saturday can wait till Monday, unless of course it’s an emergency.
I mean, if I’m working all the time, people are going to follow the leader. That’s just kind of typically how these things work. So if I’m working all the time or I’m not taking a vacation or whatever, then it’s hard for other people to feel like it’s okay for them to leave at 5:00 and for them to take vacation. So it’s really important I think for leadership to set the tone there.
Amy Elisa Jackson: What has been one of your biggest career mistakes or a decision that you wish you could walk back?
Jason Fried: This is going to sound not true, but I don’t have any, in that, I just don’t think that way. Certainly, there are things we’ve done that we could’ve done better or the mistakes we’ve made, but I just don’t ever feel like I should walk anything back in terms of what decisions we’ve made at work. I feel like it’s a continuum again, and hey look, we’re doing pretty good right now. So whatever happened before in terms of a decision we made, it was actually okay because we’re okay right now.
There’s this interesting experience I had. This was a number of years ago. I was in this shop, this place or this collector who collected Navajo rugs. And I noticed in the rugs there was a lot of … These rugs are very geometric. So the patterns are rectangles and triangles and squiggles and all these things that are very … It’s very pattern-based. And you could spot these errors in the pattern here and there. And I’d asked the person, “Why is this rug … Why is that error in here? Why didn’t they fix that?” And his take was that they didn’t actually see it as a mistake that needed to be corrected. It was just something that happened and they just kept going. It’s kind of like if you’re walking down the street, and you trip or something or you slip or whatever, it’s like, you don’t start back from the beginning of the street. You just keep going.
Amy Elisa Jackson: In culture, especially American culture, there’s this idea that a mistake is the end of the world and that, oh my gosh, everyone is going to see it and everyone is going to judge you by it. But the thought that the mistake either was supposed to happen or that it really wasn’t a mistake, it was just a decision that was made and you kind of move forward, I think that that’s something that we can all benefit.
Jason Fried: Yeah, because a lot of decisions are based on the best information you have at the time. And maybe if you look back on it, you go, “Wow, that wasn’t a great decision.” But perhaps it was a great decision or the only decision you could make or the only realistic decision given what you knew at the time. So I think sometimes we have this tendency to judge past decisions based on what we know now. But that’s not when they were made. They weren’t made now. They were made before. And further, really a mistake to me is just a moment in time, and you can’t go back. You can’t go back in time. So what are you going to do, just ruminate over this bad decision your whole life? You can’t go back in time and that’s all a decision is. It’s a moment in time. So move on, make better ones moving forward. And that’s kind of how I try to look at it.
Amy Elisa Jackson: Jason, as we wrap up, tell me, when have you felt most in control or in the driver’s seat of your career? Is it now? Is it five years ago?
Jason Fried: I guess actually that it was earlier in my career, when it was just me, when I was just freelancing and I wasn’t responsible for other people’s mortgages. I wasn’t responsible for other people’s families and putting food on the table and that sort of thing. There’s a lot of … While it’s very enjoyable to run a company of our size and of our influence and whatnot, there’s a lot of responsibility that goes into it. And the decisions affect a lot of people. I’ve always found that the fewer people my decisions affect, sort of the easier they are. And I would say probably maybe in the late ’90s when I was working on my own, I was probably in the most control of everything. I mean, technically I’m still in control, but the implications are broader and wider and deeper today than they were when it was just me.
And again, that’s not to say that I’m not really pleased with where I am today. I am, and I’m really enjoying it, but there’s just more pressure. And the thing about business and work is that it never gets easier, actually. Sometimes a lot of founders think that it’s going to get easier, like now we’re only three people, but once I can hire 100 people, everything’s going to be easier because I can have 100 people doing things instead of three. Well, it only gets harder, because you have to deal with people. People are hard to deal with, people and personalities and politics and all that stuff. It’s just, we’re human beings and we’re complicated. And the more of them around, the more complicated it gets, which is one of the reasons why we want to keep our company as small as we possibly can, just to eliminate as much complexity as possible. So I think that’s probably the honest answer.
Amy Elisa Jackson: Lastly, Jason, what are you still in pursuit of?
Jason Fried: I don’t feel like I’m in pursuit of anything. I don’t feel like I’ve ever been in pursuit of anything. I just want to try to be the best person I can be and do the best job I can do and be the fairest person I can be. I think maybe fairness in all respects is something I would say maybe I’m trying to point towards or something. But as far as pursuing and achieving, I’ve never really looked at things that way. And it’s similar because it’s kind of like the goal discussion. I think if you’re pursuing something and you get to it, well then what? Do you have to pick something else? If you don’t, then are you done with life? It’s kind of like, why set yourself up for those sorts of moments. I’d just rather try to continually do the best I can and see where things go.
Amy Elisa Jackson: Wonderful. Thank you so much, Jason, for hopping on and speaking to us here at Glassdoor. We really appreciate you taking the time.
Jason Fried: Well, thanks for inviting me on. It’s an honor and I appreciate it.
Amy Elisa Jackson: Thank you for listening to IN PURSUIT, the podcast from Glassdoor. This episode was produced by Lee Schneider and Alison Sullivan, music by Epidemic Sound, production by Red Cup Agency. Look for us on Apple podcast or wherever you get your podcasts. If you’re on Apple podcast, don’t forget to share the love. Give us some stars and leave a comment. Thanks for listening. I’m Amy Elisa Jackson, and this is IN PURSUIT.