PDF Summary:The Pathless Path, by Paul Millerd

Like most people, Paul Millerd was taught to place conventional, full-time work at the center of his life—but it made him miserable. Now, he’s a freelance blogger, consultant, career coach, and online course creator—and he’s much more satisfied with his life. In The Pathless Path, Millerd encapsulates his non-traditional approach to career success and lifelong happiness: deprioritizing work and pursuing a more meaningful, creative life through freelancing instead.

In this guide, you’ll learn about the historical trends that have led most Americans to prioritize work, the disadvantages of prioritizing work, and an alternative to this way of life—freelancing. You’ll also learn how and why Millerd shifted from the traditional workforce to the world of freelancing and his advice for making the transition yourself. In our commentary, we’ll talk about other perspectives on work and what makes life meaningful, and we’ll provide additional tips for those interested in freelancing.

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• First, learn more about the traumatic experience you’ve just had: What happened, why did it happen, and what are the consequences?

• Second, learn how to manage your negative emotions, for example via mindfulness techniques.

• Third, talk to someone (a professional or a friend) about your crisis—this will help you gain understanding and feel less alone. It can also help to hear from others about their crises.

• Fourth, decide on the story you’re telling yourself about what happened; consider both what you’ve lost and what you’ve gained (like a new perspective or clearer priorities).

• Finally, find a way to help others, as research suggests this can aid in healing and help you turn a negative into a positive.

Millerd’s Switch to Freelancing

When Millerd’s priorities changed, he knew that he needed to redesign his life around them—and the freelancers he encountered taught him that it was possible to design a life he’d truly enjoy. Now, we’ll explore how he made the switch to freelancing and what effect the switch had on his life.

How Millerd Switched to Freelancing

Millerd’s switch to freelancing was gradual: He remained traditionally employed while he explored other options. During this time, he had a few experiences that solidified his choice to start working for himself.

First, since he didn’t care as much about his job anymore, he started to put less effort into it. He continued planning a traditional career path because he still believed this was the only viable option, but his performance was tanking, and he knew he’d have to leave his job. He thought that moving to another company might solve his problem, but they gave him an unexpectedly low salary offer. He says this made him reevaluate his relationship with money: He realized he didn’t mind making less money if he could also work less and do things he genuinely enjoyed. That wasn’t possible with this job, so he rejected it.

At the same time, he launched a new freelance business as a career coach, something he genuinely cared about and enjoyed. Millerd says the exhilaration he felt as he launched his business stood in stark contrast to the dismay he felt at his regular job. Eventually he had to admit to himself—and his boss—that he didn’t really want the job anymore.

Finally, Millerd accidentally quit his job—he got into an email dispute with his manager, something he said made his manager think he’d formally quit, and he didn’t care enough about keeping his job to correct him. He had to stay on for three months to train his replacement, and he did so lifelessly. After his last day, he realized he’d been experiencing burnout—a sense of spiritless exhaustion that, he says, happens when your values and definition of success don’t align with those of the organization you work for. He realized that he wasn’t living up to his own expectations and that this was his fault for prioritizing work—so it was time for a change.

With no pressing responsibilities after he quit his job, Millerd booked a five-week vacation to Europe to relax. He explains that he didn’t feel confident about his choices or the future, but he was committed to exploring new options. When he returned to the US, the pressure to make money was back on—his savings were starting to dwindle. He decided to minimize his cost of living and took advantage of every freelance opportunity available to him—mostly consulting work with other companies.

Should You Transition to Freelancing?

Before you jump into a freelance career, you should understand your motivations for doing so. Let’s discuss some of the signs you’re ready—or not ready—to transition.

Millerd explains that he started to realize it was time for a career change when he became less engaged at work. Experts define employee engagement as an emotional commitment to your work, and they explain that low engagement may be a sign that your job isn’t a good fit for you. However, if you need to keep your job for the time being, be mindful that low engagement can negatively impact your performance, as it did for Millerd. One way to counteract this is by changing unsatisfying aspects of your job to make it feel more meaningful.

Another factor in Millerd’s decision to leave the traditional workforce was his realization that money didn’t matter very much to him anymore. Some research suggests that this was a good call—beyond the $75,000 mark, higher salaries don’t enhance your happiness. However, keep in mind that Millerd had savings to fall back on (enough that he could afford a European vacation and pay bills). If you’re not in a similar financial situation, a steady income might be more important to you than it was to him. In that case, your transition to freelancing may need to be more gradual—and it’s possible freelancing isn’t right for you at all, since freelancing is associated with higher financial insecurity.

Millerd says that when he started working as a freelancer, he knew it was a good choice because it satisfied his passions (whereas his traditional job did not). However, experts note that while having a job you’re passionate about might be good for you, turning your passions into a career can actually decrease the pleasure you take in them. Having a job you’re passionate about can also come with pitfalls like the erosion of work-life boundaries and increased risk of burnout. If you’re thinking about transitioning to a freelance career, it’s worth considering how the pros and cons of following your passions might play out in your life.

If you ultimately decide that you do want to start freelancing, you may find it helpful to ensure the transition is gradual. One way to do this is by starting a side hustle (part-time freelance work) while you hold down your regular job, as Millerd did with his career coaching business. Experts note that side hustles are becoming exceedingly common—around 44 million Americans have one.

If you decide to start a side hustle, keep reading—we’ll go over tips for getting started later. Note, however, that taking on a side hustle in addition to an unsatisfying day job may lead to burnout, since you may overexert yourself or become demoralized if you don’t see positive results quickly enough. To prevent burnout, make sure you’re doing enough self-care (like eating well and sleeping enough).

How Switching to Freelancing Changed Millerd’s Life

As a freelancer, Millerd experienced total autonomy for the first time—he could work on his own terms, which energized him. However, he realized that he still defined his identity in terms of his career, which prompted him to think about his identity outside of work. He decided to prioritize recreation ahead of work and took a break from relentlessly pursuing freelance opportunities that forced him to work on projects he didn’t truly care about.

(Shortform note: In Drive, Daniel Pink argues that intrinsic motivation (an authentic desire to do something) is what makes work meaningful—which could be why Millerd was energized by the opportunity to choose work projects he was genuinely interested in. Pink also recommends taking a break from work, like Millerd did, if you need to increase your intrinsic motivation—he explains that this gives you a chance to discover and figure out how to pursue what truly matters to you. If you’re having trouble taking a break from work because it’s tied to your identity, the best way to decouple your job and identity is by experimenting with new ideas, exploring new places, and seeking out new experiences outside of work.)

As a result of his choice to prioritize recreation, Millerd had a surge in creativity—he revamped his blog, started a podcast, and eventually started designing his own online consulting courses. This experience taught him that creative work was the only work he really found joy in. (Shortform note: It makes sense that Millerd’s creativity was enhanced when he started spending more time relaxing and having fun—according to experts, rest is foundational to creativity. When you’re relaxed, you’re not focusing on any particular subject; as a result, your subconscious mind can wander, discover new possibilities, and produce creative epiphanies.)

Altogether, Millerd’s early freelancing experiences taught him that he wanted to work just enough to sustain himself and no more than that—he was now fully committed to living life to the fullest by prioritizing recreation, exploration, and joy. He got rid of most of his belongings, moved to Taipei, Taiwan, and embraced a minimalist lifestyle: few possessions and few responsibilities. This enabled him to lower his cost of living so that he could focus on his new priorities.

(Shortform note: If you want to work fewer hours so you can spend more time on recreation, exploration, and joy, you may need to learn how to make the most of your working hours. In Do Nothing, Celeste Headlee recommends maximizing your productivity by working in short bursts with breaks in between, collaborating with others whenever possible, and doing the bare minimum since working too hard might leave you too exhausted to enjoy your free time. Minimalism might also increase your productivity—by reducing the number of possessions and responsibilities that worry or distract you, you increase your ability to focus on your work.)

Millerd also decided that instead of living for the weekend or waiting for retirement to do what he cared about, he’d incorporate exploration into his regular life by devoting intense energy to a new experience (like learning a new language or traveling) for a short period of time, then resting and moving on. He explains that this is a great way to experiment with what makes you happy—you’re not exhausting yourself by overcommitting, and you gradually figure out what really makes you happy and should be incorporated into your day-to-day life when you do eventually retire.

(Shortform note: In How to Do Nothing, artist Jenny Odell says there’s also some value in exploring the world around you (as opposed to traveling elsewhere). She recommends using your free time to explore three facets of your daily life: the nature that surrounds you, the history of the place where you live, and the people who live near you. According to Odell, exploring these things will make you feel more connected to and appreciative of your community. One benefit of exploring close to home rather than far-off places and cultures is that this is easy to incorporate into your daily life right now, as Millerd suggests you do—you don’t have to wait until you can afford a vacation or retirement.)

How to Deprioritize Work

Based on the lessons he learned from his own career, Millerd offers advice for anyone who’s looking to deprioritize work by becoming self-employed. This advice can be collapsed into three essential steps: altering your mindset, finding your niche, and adjusting to your new lifestyle. Let’s explore each step in detail.

Step 1: Alter Your Mindset

According to Millerd, since we’re all taught that prioritizing work is the best or only viable life path, to make a change you must first unlearn that idea and open your mind to the alternatives. He suggests that you do so by reinventing success, facing your fears, and discovering new values.

Reinvent Success

Millerd explains that most people hold two mistaken beliefs about success: First, they believe that they’ll only be judged as successful if they meet certain socially determined benchmarks, which usually represent the accumulation of wealth or social status (for example, some people define success as becoming debt-free). This is mistaken because studies suggest that most people care more about living their values to the best of their ability than adhering to social standards.

(Shortform note: In The Seven Spiritual Laws of Success, Deepak Chopra explains in greater detail why external factors like wealth or social status aren’t good markers of success. He argues that external markers of success are ephemeral, which gives you anxiety and leads you to make unwise decisions in a frantic attempt to hold onto them. For example, you may become willing to step on others to keep a high-paying job that makes you feel important and secure. Chopra says it’s better to prioritize what’s spiritually meaningful to you since the joy you experience from achieving goals that align with those priorities is more sustainable.)

Millerd says the second mistaken belief people have is the “arrival fallacy”—the belief that once you achieve a given benchmark, like buying a house, you’ll be happy once and for all. When they inevitably find that it doesn’t make them permanently happy, they apply the same thinking to another, loftier goal. Millerd says this is mistaken because nothing can give you permanent happiness.

(Shortform note: Experts explain that the arrival fallacy isn’t just unrealistic—it can also put you at risk for depression. If your expectations about what you’ll feel when you achieve a goal are too high, you become disillusioned when the results aren’t what you thought they’d be, which can lead to a general sense of demoralization. To avoid falling for the arrival fallacy, experts recommend living in the present instead of focusing on future goals, practicing gratitude, and enjoying the process of working toward goals instead of prioritizing the end result.)

Instead of falling for these mistaken beliefs, reinvent success for yourself. Millerd recommends measuring success in terms of contributing something important to the world and living according to your values. He explains that this dynamic process will naturally bring recurrent joy to your daily life, whereas static achievements like home ownership happen one time only and are innately less fulfilling.

(Shortform note: Research on happiness supports the notion that you should measure success in terms of your integrity and your contributions to society. First, living your values helps you prevent cognitive dissonance—an uncomfortable sense that you’re not doing what you should—and achieve cognitive consonance instead, which reduces anxiety and helps you feel like a good person. Second, contributing to society satisfies a basic psychological need. Humans are an interdependent, social species, so feeling connected to others enhances well-being, and studies suggest that helping others is a powerful way to reinforce this sense of connection.)

Face Your Fears

Reinventing success can often provoke fear—for example, you might worry that deprioritizing work will make you go broke. When you’re afraid of the consequences of reinventing success, Millerd recommends the following practice:

First, write down the worst possible scenario and some steps you could take to recover from it. (for example, if you became homeless, one step toward recovery might be accessing a shelter). This step makes your fear more manageable by transforming vague anxiety into tangible concerns and instilling confidence that you can handle setbacks. Then, write about what could go right—the opposite of the worst possible scenario—and what you might lose out on if you don’t take this risk. This step makes your fear more manageable by shifting your focus from risks to benefits.

(Shortform note: In Courage Is Calling, philosopher Ryan Holiday offers more advice about facing your fears as you make risky decisions. First, he recommends that you embrace uncertainty. He explains that even if you make the safest choices possible (like staying in the traditional workforce), there’s still a chance that something could go wrong, so you might as well take the leap and pursue the option you truly desire instead of prioritizing security. Second, he says you should make a bold decision and stick with it. If you spend a lot of time weighing the pros and cons of your choice to deprioritize work, you’re really choosing to stay stuck in your rut, which robs you of time you could be devoting to a better way of life.)

Discover New Values

When you let go of society’s definition of what’s important, you must replace it with a new set of personal values. Millerd says the best way to discover your new values is by noticing what draws your attention. He explains that when you begin to question what makes life worth living, you’re naturally drawn to seek out new experiences—and he says the experiences that hold your attention are typically what’s most important to you. You may also return to experiences that held your attention during childhood—for example, maybe you used to love making music but stopped when you became an adult and got a traditional job that sucked the life out of you. In that case, it may be time to explore making music again.

(Shortform note: Experts suggest that the relationship between what you value and what you pay attention to is complex—while studies affirm that visually speaking, your focus is naturally drawn to elements of your environment that you value, it’s also true that you may focus on distractions that aren’t all that important to you (for example, maybe you spend a lot of time on social media even though you don’t think it’s high-value). In The Subtle Art of Not Giving a F*ck, Mark Manson offers another method for defining your values—focusing on your emotional responses to stimuli. First, notice your emotions; next, evaluate why you feel the way you feel. Then, ask yourself how those emotions relate to your definitions of success and failure.)

Millerd also suggests that you graciously accept differences of opinion. Many people in your life will still define success in traditional ways, which means they might not understand or approve of your decision to design your life around different values. That’s OK—they don’t have to. What matters is that you understand and approve of your new values.

(Shortform note: When your values clash with those of other people in your life, psychologists suggest you follow these steps to achieve a resolution: First, define the values in question on both sides. For example, maybe you value freedom while your partner values financial security. Next, each of you should explain why you value what you value and how it relates to the situation at hand; this can support mutual understanding. Finally, find a compromise by choosing a course of action that honors both sets of values if that’s possible.)

Step 2: Find Your Niche

Once you’ve altered your mindset, it’s time to pursue a more personally meaningful life. Most people assume that deprioritizing work means rashly quitting your job with no backup plan, but Millerd explains that the transition from traditional work to self-employment should be a gradual process. It takes time to figure out what you’re going to do next, and if you make rash decisions, you might suffer negative consequences that put you in panic mode, which limits your freedom to make the decisions you genuinely want to make.

(Shortform note: As you gear up to leave your traditional job, you might consider quiet quitting—a form of subtle disengagement from the job that involves doing only the bare minimum. That way, you can continue performing as well as you need to in order to keep bringing in a paycheck while refocusing your remaining energy on the next steps.)

Many people are intimidated by the freedom that self-employment gives them—how do you decide what to do with your time? Millerd says that you can only find your niche via trial and error: Try a new approach to work and see how it feels. If you like it, do it again; if you don’t, try something else. He explains that you’ll know you’ve found your niche when something meets the two conditions of reinvented success: It enables you to live according to your values and contribute something important to the world.

(Shortform note: in What Color Is Your Parachute?, career expert Richard Nelson Bolles says finding your niche is easier with self-reflection. He recommends considering seven factors as you reflect: the kinds of people you want to work with, the conditions you prefer to work under, your skillset, your life purpose, the knowledge you already have, your financial goals, and your ideal place to live.)

Millerd argues that creative work is key to a meaningful life—so your niche will probably be a creative endeavor. He explains that everyone has an inherent capacity for creativity and that creative expression is becoming more democratically available thanks to the internet—anyone can post self-produced music online, for example.

(Shortform note: Some researchers say that one reason creativity makes life more meaningful is that it deepens your relationship with yourself. Through creative work, you have the opportunity to explore and reflect on your thoughts, beliefs, feelings, and experiences. This process can help you cope better with adversity and produce results you find personally valuable, which is correlated with enhanced joy.)

Millerd also encourages you to share your work online because although there’s a chance people will dislike it, there’s also a chance that people will love it—and if they do, it might open the door to further opportunities to do what you love.

(Shortform note: In Steal Like an Artist, writer and illustrator Austin Kleon says you should be careful not to rush the decision to start sharing your creative work online. He explains that when you’re anonymous, you have the freedom to experiment—but once you start sharing your work, people will expect you to keep doing the same thing. When you know you’re ready to share your work, Kleon suggests that you create a website and join social media, where you can share both finished work and sneak peeks at ongoing creative processes.)

Once you find something you want to stick with, engineer a life that enables you to continue doing it. For example, if you discover a passion for music but can’t get paid for it yet, you may have to take on paid freelance work to support yourself until you can make music profitable. Millerd suggests minimizing risks to your security as much as possible: For example, he recognized that freelancing is a fickle industry since work isn’t steadily available or well-paying, so he set himself up with multiple streams of income (including freelance consulting work and selling online consulting courses) so he always has something to fall back on.

(Shortform note: As you work on engineering a life that enables you to continue working in your niche, it may help to build flexibility into your plans. In Designing Your Life, Bill Burnett and Dave Evans suggest that you generate three five-year plans: one plan that would support your current career path, a backup plan in case the first plan falls through, and a third plan for what you’d do if you weren’t concerned about money or other people’s approval. This could help you adapt to unexpected circumstances that might arise as you pursue your new career.)

Step 3: Adjust to Your New Life

Once you’ve found a niche and designed your life around it, Millerd says you’ll need to make major adjustments to your money habits and your motivation habits. Let’s explore this further.

Adjusting Your Money Habits

In the traditional workforce, you have a steady stream of income, and—according to society, at least—you should be consistently building wealth for the rest of your life. In contrast, self-employment rarely comes with a stable income, and according to Millerd, you’re not likely to become very wealthy. To deal with these differences, he suggests making the following adjustments:

Instead of pursuing exponentially growing wealth, pursue sustainability—making just enough money to meet your needs. When you’re always trying to make more money, you lose some of your freedom: You can’t say no to any opportunity to make money, no matter how miserable it makes you, and you can’t say yes to opportunities that are more emotionally rewarding than financially rewarding. On the other hand, when you deprioritize work, you’re saying that enjoying life is more important to you than having a lot of money—so aim to bring in an income that enables you to enjoy life.

(Shortform note: In Minimalism, Joshua Fields Millburn and Ryan Nicodemus argue similarly that sustainability is a much better goal than a life of excess. If you tend toward excess and want to change that, they recommend starting by identifying your anchors (possessions or financial responsibilities that make you feel stuck). Then, classify those as major anchors (large responsibilities like car payments) and minor anchors (small responsibilities like clutter). Finally, get rid of as many anchors as you can, starting with the major ones. They say this will reduce your stress, free up your time, and help you find overall happiness.)

Live more frugally. You’re trading higher pay for a higher quality of life, so you need to make every cent count. Millerd recommends spending money only on the things you need to be happy and cutting extra costs wherever possible—that way, you can spend less time working and more time enjoying life (by spending time with your family, for instance).

(Shortform note: To live more frugally, experts recommend keeping track of your expenses for a month or two, and then evaluating them: What’s necessary, and what’s not? Then, cut back on any extra purchases that don’t add value to your life. According to some research, valuable purchases include those that save you time (which you can reinvest in enjoyable activities) and those that enable you to have meaningful experiences, as opposed to just accumulating material goods.)

Learn to live with insecurity. Millerd argues that no amount of money can guarantee total, everlasting security. Even if you had a million dollars in the bank, something could happen tomorrow to wipe out your funds. He says that worrying about the future is an unavoidable part of life, and it’s healthier to accept and deal with those worries as they come up than to avoid worrying entirely.

(Shortform note: In The Wisdom of Insecurity, philosopher Alan Watts argues similarly that insecurity is a fundamental part of human life. He explains that this is because life is inherently ephemeral—everything is in a constant state of flux. He says that trying to achieve security can only lead to further misery because the desire for security is based on an illusion that you can achieve a state of permanence. As an alternative to worrying about the future, he suggests embracing insecurity and going with the flow from moment to moment.)

Embrace generosity. Millerd explains that flexible payment models are becoming more popular—for example, many freelancers offer subscriptions to their services via platforms like Patreon and pay-what-you-want options for people who may not be able to afford their services. He explains that people usually appreciate these payment models because they’re voluntary and fair—so they’ll be generous with the amount of money they give you. You should also be generous with others, as Millerd says that will increase the likelihood of others being generous with you.

(Shortform note: Experts note a potential drawback to flexible payment plans—you might not bring in a large enough income. According to public data, a very small percentage of Patreon creators bring in more than the US federal minimum wage ($7.25 per hour). Some businesses that offer a pay-what-you-want option have suffered major earnings losses. Research suggests that to make a profit with flexible payment plans, you need to build up a large base of loyal customers—the more stable their relationship with you, the more likely they’ll be to pay you fairly, and having a large number of customers can make up for the times when some customers don’t.)

Adjusting Your Motivation Habits

With a traditional job, it’s easy to know whether you’re on the right track—either you’re performing well and achieving traditional benchmarks, or you’re not. When you’re self-employed, it’s a little more complicated—and insecurity about whether you’re doing the right thing can diminish your motivation to keep going. To minimize your insecurities and stay motivated, Millerd recommends making the following adjustments:

When your ultimate goal is unclear, define what you don’t want to happen and figure out what steps to avoid taking so that it doesn’t occur. If you find that you’re on the path to making that bad outcome happen, you need to make changes. If not, you’re probably doing OK. To illustrate, suppose your worst fear is becoming destitute. If your current work situation isn’t paying your bills or is causing you to go into outrageous debt, you probably need to revise your approach to work.

(Shortform note: Psychologists distinguish between avoidance goals like Millerd describes, where you’re focused on avoiding a poor outcome, and approach goals, where you’re focused on pursuing a positive outcome. Some experts say that avoidance goals are typically less motivating than approach goals—and research suggests that pursuing more avoidance goals than approach goals can lead to poorer self-esteem, increased procrastination, and decreased satisfaction with both your goal-related progress and your life in general. For that reason, they suggest transforming avoidance goals into approach goals when possible—for example, instead of trying to avoid destitution, you might aim to build an emergency fund.)

Stay adaptable. Millerd says that change is inevitable—work opportunities will come and go, your financial situation will vary, and you may even revise your values and definition of success. Instead of resisting change, prepare yourself to go with the flow and have faith that even though you don’t know exactly what’s going to happen, it’s going to be OK.

(Shortform note: In Who Moved My Cheese?, Spencer Johnson offers some tips for adapting to work-related changes. These include staying abreast of signs of change so that you can better prepare for it, accepting that the prior state of things no longer applies, and focusing on the potential benefits of the change instead of the things that scare you about it.)

Connect with supporters and mentors. Supporters are those who believe in your ability to live a meaningful life outside of traditional parameters, and mentors are those who can teach you how to do that because they’re already doing it themselves. Millerd notes that social media is a great avenue to find supporters and mentors—people who openly share their life stories online can learn from each other, and you may even be able to find an online community created for people in situations like yours.

(Shortform note: In Never Eat Alone, entrepreneur Keith Ferrazzi says there are two methods to connect with supporters and mentors online. The first method is approaching prospective supporters and mentors directly—you can decide who you’re interested in networking with, follow and message them, and eventually try to meet in person. The second method involves posting interesting content to your social media that will compel prospective supporters and mentors to reach out to you instead.)