4023: How to Do What You Love and Make Good Money AND Quitting Something You Love by Derek Sivers
Optimal Living DailyMay 22, 2026
4023
00:10:02

4023: How to Do What You Love and Make Good Money AND Quitting Something You Love by Derek Sivers

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Episode 4023:

Derek Sivers explores why the happiest and most fulfilled people often separate financial stability from creative expression instead of forcing one pursuit to satisfy every emotional and practical need. He also reflects on the surprising freedom that comes from quitting even the things you love, showing how letting go of comfort and dependency creates space for growth, reinvention, and a more intentional life.

Read along with the original article(s) here: https://sive.rs/balance & https://sive.rs/quit

Quotes to ponder:

“Do something for love and something for money. Don’t try to make one thing satisfy your entire life.”

“Most full-time artists I know only spend an hour or two a day actually doing their art. The rest is spent on the boring work that comes with trying to make it a full-time career. So skip the art career and just do the art.”

“You don’t need to compromise your art or value it based on others’ opinions.”

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[00:01:00] [SPEAKER_01] This is Optimal Living Daily. How to do what you love and make good money. And quitting something you love. Both by Derek Sivers of Sivers. That's S-I-V-E dot R-S. And I'm Justin Malik. Happy Friday. Welcome to Optimal Living Daily. Happy Friday. Welcome to Optimal Living Daily or Old. One of a few shows where we read articles to you. So with that, let's get right to it. Two posts actually. As we optimize your life.

[00:01:30] [SPEAKER_01] How to do what you love and make good money. By Derek Sivers of Sivers. That's S-I-V-E dot R-S. People with a well-paying job ask my advice because they want to quit to become full-time artists. But full-time artists ask my advice because they're finding it impossible to make money.

[00:01:49] [SPEAKER_01] Let's define art as anything you do for expression, even just blogging or whatever. For both of them, I prescribe the lifestyle of the happiest people I know. Have a well-paying job and seriously pursue your art for love, not money. Let's look at the ingredients of this plan. First, balance. You've heard about balancing heart and mind or right brain, left brain, or whatever you want to call it.

[00:02:18] [SPEAKER_01] We all have a need for stability and adventure, certainty and uncertainty, money and expression. If you have too much stability, you get bored. If you don't have enough stability, you panic. So keep the balance. Do something for love and something for money. Don't try to make one thing satisfy your entire life.

[00:02:41] [SPEAKER_01] Each half of your life becomes a remedy for the other. You get paid stability for part of your day, but then need creative time for expression. So you push yourself creatively, expose your vulnerable art to the public, feel the frustration of rejection and apathy, and then long for some stability again. Each half is a remedy for the other. About the job? Be smart and choose something that pays well with a solid future.

[00:03:08] [SPEAKER_01] Look for statistics in your area about what pays the best when factoring in the required training. You'll probably need to study for a few years to build up the rare skills that are well-rewarded. This is a head choice, not a heart choice, since you're not trying to make your job your entire life. About your art? Pursue it seriously. Take lessons. Make weekly progress. Keep improving, even if you've been doing it for decades.

[00:03:33] [SPEAKER_01] If you don't progress and challenge yourself creatively, it won't satisfy the balance. Release and sell your work like a professional. Find some fans. Let them pay you. But your attitude is different than someone who needs the money. You don't need to worry if it doesn't sell. You don't need to please the marketplace. You don't need to compromise your art or value it based on others' opinions. You're just doing this for yourself. Art for its own sake.

[00:04:01] [SPEAKER_01] And you're releasing it because that's one of the most rewarding parts, important for self-identity, and gives you good feedback on how to improve. Your main obstacle to this amazing life will be self-control. You'll need good time management to stop addictions like social media and video watching, and make your art your main relaxing activity. You'll need good mind management to not think of your job after you leave the office.

[00:04:26] [SPEAKER_01] Most full-time artists I know only spend an hour or two a day actually doing their art. The rest is spent on the boring work that comes with trying to make it a full-time career. So skip the art career and just do the art. That's my advice for a rewarding life. I've met thousands of people over the last 20 years, many of them full-time musicians, many of them not. But the happiest people I know are the ones that have this balance.

[00:04:53] [SPEAKER_01] Don't expect your job to fulfill all your emotional needs. Don't taint something you love with the need to make money from it. Don't try to make your job your whole life. Don't try to make your art your sole income. Let each be what it is and put in the extra effort to balance the two for a great life. Quitting Something You Love by Derek Sivers of Sivers. That's S-I-V-E dot R-S.

[00:05:23] [SPEAKER_01] Personal change needs some space to happen. To bring something new into your life, you need somewhere to put it. If your current habits are filling your day, where are these new habits supposed to go? The English word quit comes from Old French meaning to free or to release. We know about quitting something that's bad for you or something you hate. But what about quitting something you love? I rebel against anything that feels like addiction.

[00:05:49] [SPEAKER_01] When I hear myself saying, I need this, I want to challenge that dependency and prove my independence. It's usually something tiny. For example, I used to keep mints in the car. One day when I ran out, I thought, oh no, I need more. But as soon as I felt that need, nope, time to quit. No mints in the car since that day. Sometimes it's something big. I used to have an awesome job. I loved it so much that I became too comfortable.

[00:06:18] [SPEAKER_01] So I made myself quit. That made me figure out how to be a full-time musician. Ten years ago, I felt addicted to America. It was my comfort zone. I loved it too much. I couldn't imagine living anywhere else. So I made myself quit. I haven't lived there in ten years and probably never will again. People often ask if I miss it. Any regrets? Not at all. I still love everything I quit,

[00:06:44] [SPEAKER_01] but not as much as I love all this room for change. You just listened to the posts titled, How to Do What You Love and Make Good Money and Quitting Something You Love, both by Derek Sivers of Sivers. That's S-I-V-E dot R-S. And I'll be right back with my commentary. Now I've gone to the doctor with fatigue and got a sleep study which showed nothing. No real data, no plan.

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[00:08:36] [SPEAKER_01] Thank you to Derek. Doing what you love and making good money is a tough one. Am I doing what I love? Yes and no. 100% I'd rather do this than any other job I've had in the past. But does my workday consist of me smiling as I'm working, laughing, feeling like all of my potential and dreams are being released or fulfilled? Not really. Being an entrepreneur means doing everything, especially when first starting out, literally everything,

[00:09:06] [SPEAKER_01] since you're probably the only person working on it. And that was the case for me. As people got added to the team, some help with editing, since we're producing so many daily shows, new hosts hosting the other shows and all that, my duties kind of shifted around from technical to more social and management. Does that make them better? Not really. Different, yes. But the tasks themselves and the work involved, not necessarily better. However, the thing is,

[00:09:35] [SPEAKER_01] once a creative project turns into our job or our livelihood, that means it turns into work. And that takes away the freedom and enjoyment of it. Not all of it, that's for sure, but definitely a large part of it. So Derek's suggestion of keeping a well-paying job while seriously pursuing your art for love and not for money, not worrying about that, it makes perfect sense to me. I started out with entrepreneurship keeping my other job too. And I think it's good advice,

[00:10:03] [SPEAKER_01] along with the advice about balance. We don't want too much stability or too much certainty. We'll reject it. It's all about balance. So try to find that balance today. Hope you enjoyed these ones from Derek. Thank you for being here and following or subscribing. And thank you so much if you've ever shared the show with someone. That goes a really long way to keep all of this going. Hope you're having a great Friday if you're listening in real time. And I'll see you tomorrow, over the weekend, where your optimal life awaits.