25 Years Without a Job

It’s been 25 years since I last had a job working for someone else, so I thought I’d share some reflections on what life is like on the jobless path.

Freedom to Choose

The most basic benefit of not having a job is exactly what you’d expect. There’s a lot more freedom to choose how to spend your time and what kind of life to create. This is indeed a powerful benefit, one that takes years to fully realize though.

When you aren’t tethered to a job, it becomes obvious that you’re responsible for your affairs and that you’ll need to make the big decisions yourself. This level of freedom can feel overwhelming at times, and it’s unrealistic to think that you’ll somehow create a masterful life in the first six months. You’ll still be limited by your ability to mentally and physically create the reality you desire.

On this path your personal shortcomings feed into your lifestyle limitations, so this is almost by definition a very growth-oriented path to pursue.

This is also a path of self-trust. The one time I had a job, I became an employee because I didn’t really trust myself, and I felt I needed the stabilizing effect of following orders for a while. After several months I realized that I could and should trust myself to lead my own life instead of hiring a boss to manage part of it for me. Surely I’d make some mistakes, but I’d learn and grow from them. And that is indeed what happened.

Achieving Goals

I like that I’ve been able to achieve a variety of personal goals that would have been hard to achieve if I had a job all this time. I created and published several computer games. I wrote a book and saw it published in many languages. I served as president of a non-profit association. I built two successful businesses. I traveled to many places I’ve always wanted to visit like Paris, London, Berlin, Rome, Amsterdam, and more. I built two successful forum communities. I trained in martial arts and ran a marathon. I designed and delivered 16 three-day workshops. I’ve made some unusual and interesting friends.

Or I could have worked at regular jobs for the past 25 years, in which case I probably wouldn’t have accomplished such a variety of personal goals. I would have built a career instead of having a life. Instead of collecting so many amazing memories, I’d be looking back on a much more mundane timeline of my past. I’m sure I still would have accomplished a lot, but those accomplishments would have been less varied and more constrained.

Instead of having to work on achieving an employer’s goals, I love working full-time on my own goals. I don’t have to squeeze my goals into my after-work hours. I don’t even have to squeeze them into my work hours. If a goal is important enough to me, I can push work aside and go after the goal full steam ahead.

This year my big goal is creating and launching Conscious Growth Club, a long-term project I’ve been working on for a few months now. It’s a challenge to be sure, and I’m loving the process of co-creating it with other personal growth enthusiasts. I can’t fathom how I’d tackle a project like this if I had a job sucking up my time and energy.

It’s also great that my work keeps pace with my skills because I decide which goals to set. I don’t have to be bored because my work is too easy or stressed out because it’s too hard. I can keep myself in the sweet spot of motivation by choosing goals wisely. This leads to bursts of high motivation where it’s fun to plow through 12+ hours of stimulating work in a day, followed by extended breaks for rest, play, and social time.

There’s just no substitute for holding the reins and being captain of your own ship.


One of the key benefits of this path is being able to express my values more congruently than I could if I’d had a job all this time. The more I follow this path, the more it sinks in that my life is my responsibility, and I don’t have to live like everyone else does. I can do things my way because I don’t have a corporation dictating how I manage my time or run my affairs. I’m not a cog in someone else’s machine.

That entails more responsibility of course. I can’t turn around and blame my boss or company when I make mistakes. I have more freedom to experiment, to take risks, and to fail, so the responsibility for my results is more obvious. I can’t just gripe about excess bureaucracy or company politics to let myself off the hook. I’m always on the hook for how my life turns out.

Many people with jobs have to deal with values conflicts with their employer. For instance, you might care about helping customers solve their problems, but maybe your employer wants you to push for more sales. Or you might value good health habits while your company succumbs to a culture of junk food and soda. And quite often employers have chaotically shifting values that are unclear, so you never know whether you’re aligned with them or not.

Values conflicts are a part of life, but without a job, I eliminate many of these issues from my day-to-day life, so I’m able to express my values more congruently. I can write about any topics I desire with no censorship of my ideas. When I eat lunch at work, all the food is vegan. I keep my website free of third-party advertising since I don’t want to distract my readers with clutter. I can take as much vacation time as I desire, and no boss will ever complain.

This works well if you’re very self-motivated. If you need someone to pat you on the back for every accomplishment, like receiving a positive evaluation from your boss, you might miss having people formally recognize your successes. Without a job your motivation has to be more intrinsic to stay on track. You need to be satisfied by the natural rewards of accomplishing your goals and expressing your values because sometimes you’ll be the only one who cares or notices.

Financial Freedom

It took me several years and a bankruptcy to achieve the level of abundance I wanted. Lots of entrepreneurs struggle in the beginning because there’s so much to learn, and so many mistakes are possible. But if you’re intelligent, flexible, and willing to learn from those with more experience, you can eventually enjoy financial abundance without needing a job. This means that money is no longer a serious limitation to creating the type of life you desire.

When money is abundant, it becomes obvious that time is really the scarcest resource. Consequently, having more financial freedom can actually motivate you to improve your time management and to overcome procrastination. You’ll soon realize that money has no power of its own. Fat stacks just sit there and do nothing by default. It takes time to spend money if you want to spend it wisely.

As many friends who’ve built passive income streams have discovered, achieving financial abundance doesn’t automatically create an awesome life. Far from it! You still have to invest your time, energy, and intellect into figuring out what to do with your time. Even if you just travel around, it takes effort to figure out where to go next. It takes effort to figure out what to do each day. And if you aren’t careful, you could fall into a slump of depression if you allow yourself to slack off from personal growth.

Having more money won’t wipe out your problems. It will simply give you a different class of problems to deal with. The post-abundance challenges aren’t any easier than the pre-abundance challenges, but in some ways it’s easier to fall into a slump on the post-abundance side because you don’t have so much financial pressure pushing you to take action. You have to learn how to motivate yourself with positive action even in the absence of financial pressure. For some people this is really hard to do.

I know – it’s an enviable problem to have, but in practice it’s a real challenge to figure out how to spend one’s time when money isn’t such a limiting factor anymore.

I learned that money is a downright awful motivator for me. Even when I was broke, I couldn’t get very excited about following through on action steps to earn more money. Whenever I tried to earn more, I encountered failure, resistance, and setbacks. My path to abundance was to focus on creating a purposeful and fulfilling life regardless of how much money I had. That mindset was my path to abundance.

In retrospect this makes sense because money is a social instrument – really it’s a form of social debt – and trying to make people become indebted to you isn’t very inspiring. Focusing on the social side instead of the instrument side makes a world of difference since then you’ll be thinking about doing something that matters to your fellow human beings. The social side gets you taking actions that lead to social exchanges, whereby money can finally flow to you. Money flows to you through other people. If you focus too much on the money, the people aspect might block you from receiving.

I think many of us perpetuate our financial problems so we can avoid dealing with the bigger, scarier challenges like how to invest our precious days while our death timers are counting down. It can be less harrowing to deal with the challenges of financial scarcity instead of facing harder questions like, What should I do with the next decade of my life? Sometimes it’s easier to worry about the bills instead of your relationships, your life purpose, or your entire existence.

Finding the Best Rhythms

In order to feel grounded and to be reasonably productive, I need to have some structure in my life. In some ways this is easier without a job, but in other ways it’s harder. I don’t inherit the built-in structure of a job, but I can define my own working rhythm that may be a much better match for my personality and goals. I can also do a better job of integrating my work and my personal life. My personal world and my business world can be the same world.

I began today with my usual morning routine. I got up at 5am, went for a run while listening to some podcasts; did some stretching; sat in the park and reflected on life, the universe, and everything; had oatmeal with fresh blueberries for breakfast; and started my workday. I love to begin my days with cardio exercise because it’s an instant mood booster, it strengthens my self-discipline, and it rebalances hormones and neurotransmitters, so I feel mentally sharp for the coming day.

When I had a job, I didn’t care so much about optimizing my startup routine for each day. There was a disconnect between my productivity and my results. As an employee I sometimes prided myself on how little real work I got done each day. I didn’t like my boss, especially due to his bad temper and his use of fear tactics to manage people, so perhaps being unproductive was my way of punishing him for being such a jerk.

Without a job, however, being unproductive makes no sense since it’s clear that I’m wasting my precious life. So I’m very motivated to stay sharp and squeeze a lot of juice out of each day. If I don’t keep my standards high, I suffer for it, and there’s no one to blame but myself.

If I ever slack off, I can reboot myself whenever I want. I don’t have to wait till the end of a shift or a weekend. I can set new goals or pivot to a different rhythm whenever I experience one of those golden awareness boosts. If I want to start a new habit trial, I can kick it off as soon as I’m ready. I don’t have to work around my employer’s schedule.

If I feel unmotivated or burnt out, I can take a vacation starting the very next day (or in some cases, the same day). I can stay on vacation for as long as I want. I’ve taken breaks for 30+ days more than once. Taking a full month off can be very restorative, and I usually hit the ground running when I return.

I write when I’m inspired to write, not on some employer-dictated schedule. I don’t arbitrary say to myself, “I have to blog something today.” What draws me to the keyboard is when I’m struck by an idea. I’ve gone as long as seven weeks at a stretch without blogging, and it’s totally fine. It wouldn’t suit me (or my readers) to crank out drivel on a schedule. I’d rather write only when I have something inspired to communicate.

This isn’t the industrial age anymore. Working on a 9-5 schedule isn’t well suited to today’s best opportunities for creative knowledge workers. I feel fortunate that I don’t have anyone imposing such a schedule on me. Discovering my own best rhythms has enabled me to crank out 2 million words for 100 million readers over the years.

My best working rhythms would most likely be punished by an employer. I love putting in 12+ hour days when I’m inspired to work, sometimes for weeks at a stretch. Then I need time to disappear for a few weeks, travel, explore, and switch to a different mode of living – sometimes with less than 24 hours advance notice. During that time off, my subconscious continues working in the background and chewing on problems, frequently feeding me fresh ideas and helping me to figure out new goals. Eventually I can’t hold back the creative pressure anymore, and I’m eager to pounce back into work mode for another cycle. At my best I’m a burster, not a plodder. But what employer respects such a mode of working? If you find an employer like that, maybe that’s a job you should actually consider.

Social Freedom

If I had a job, I’d probably socialize with the same people every day, which could lead to a stagnant social life. I like having the freedom to choose the people I connect with each day instead of inheriting whatever social mandates are assigned by an employer. If someone rubs me the wrong way, I don’t have to deal with them. I can fill my life with friends that I actually like, and we connect socially by choice, not by forced circumstances.

How many people do you connect with each day that you actually like? Most of the social connections I have are with people I genuinely like. If I didn’t like them, I wouldn’t connect with them.

Being self-employed can lead to spending a lot of time alone, especially if you have an Internet business. If you go to an Internet marketing conference, you’ll probably find that the room is 80-90% introverts. Same goes for the speakers. Many of the people you’d think must be total extroverts based on their effervescent YouTube videos are actually quiet and shy when you meet them in person. They can look extroverted when they’re making videos by themselves, but connecting face to face is very different.

Many introverts are perfectly fine with this, preferring to cocoon themselves and do most of their interactions from behind digital devices. If that’s your cup of tea, you might really like life without a job. You can pretty much run your whole life this way today. Or you might prefer a job that minimizes human interaction.

I didn’t want to go that route though since I felt it wouldn’t be as growth-oriented for me, so in the same year I started blogging, I also joined Toastmasters International to develop my public speaking skills. I did this partly to create a better social balance for my life and business. I’m so glad I did that because it gives me the freedom to live as an introvert or an extrovert without being forced to pick a side. Sometimes I love getting away from the computer to engage with people face to face through speaking, workshops, meetups, and traveling. Other times I feel a little overwhelmed with socializing and crave a few weeks to work alone or to enjoy life with my girlfriend.

It’s fair to say that managing my social life has been my biggest challenge since I started blogging. It takes some real conscious thought to strike the right balance, and the right decisions aren’t always clear. I’ve gone through multiple rounds of social expansion and withdrawal to wind my way to a feeling of social abundance that isn’t overwhelming. Building Conscious Growth Club is one of the expansion phases.

I tend to make new friends easily, so I’m glad I don’t have to settle for a socially stunted life. I like having lots of stimulating, growth-oriented friends. I also like having the freedom to create a social life that works for me. I shudder to think of how repressed I’d be socially if I had a job that stunted my ability to thoughtfully manage this part of my life.

I think what I’ve most enjoyed on the social path is meeting other growth-oriented people who like to zig while the rest of the world zags. These people add tremendous richness to my life. And they give me hope that together we may someday entice the rest of the world to stop zagging so much. Haven’t we zagged enough already?


Exploring personal growth is my passion, and it would be tough to fully explore this passion if I was tied to a job that limited what I could do.

If I had a 9-5 job, could I have done experiments with polyphasic sleep, water fasting, or going to Disneyland for 30 days in a row? That’s doubtful. Maybe I could do short-term experiments during vacations, but I couldn’t make these kinds of explorations part of my normal lifestyle. And I don’t necessarily want to chew up my vacation time dealing with no sleep, no food, and endlessly looping Disney music.

(As a side note, I finally got most of the Disney music out of my head, but now I’m stuck with the addictive songs from La La Land. And whenever they start to fade, Rachelle starts singing them again.)

Would I have gotten fired for blogging about open relationships or D/s play? Maybe. It would depend on the employer, but who wants to wear a social mask to please their boss? It’s easier just to be myself. I don’t want to have to pretend to be someone else each time I go to work.

I think many people hide behind their jobs as a convenient excuse for not exploring their desires. Exploration involves taking risks and facing fears. It’s easy to settle into a job and tell yourself that you don’t have the time, freedom, or money to identify, clarify, and pursue more interesting goals. Just getting clear about one’s desires can take a lot of work, let alone carving out the time to actually explore them.

I can get wrapped up in my business too, but it’s harder to pretend that I’m not in control of my explorations. If I’m not exploring something I really want to, I have to face and work through the inner resistance. I can’t just externalize an excuse and expect myself to believe it.

The result is that I explore a lot more than I would if I had a job. I don’t have to schedule my explorations during the gaps in my job. I can weave them into my work as well, and there doesn’t need to be a sharp separation between work, life, and play.

Location Freedom

A job can tie you to a single location, but without a job, you can go wherever you want, whenever you want. You can even live on the road if you like.

I once fantasized about going fully nomadic, but I like having a stable home base to come back to, and I sometimes feel burnt out from traveling too long at a stretch. I’m more productive in my home office, and some experiments are much easier to do at home. What works well for me is to oscillate between time at home and time on the road. I’ve gotten pretty good at taking spontaneous trips when I feel it’s time to get away from my desk.

I love that travel isn’t just a dream, but it’s something I can make real whenever I want. Going to other cities and countries has enriched my life tremendously, and I see this being a part of my lifestyle for decades to come.

Skill Breadth and Depth

As an employee I might be able to get by with a narrow set of skills, but to survive and thrive without a job, I’ve had to develop a great variety of skills.

As I shared in the article Mile Wide, Mile Deep, going broad with a skill set doesn’t mean being shallow. You can actually gain more depth from complementary skills that enhance each other.

On my path without a job, I’ve developed skills in programming, writing, business, public speaking, negotiation, coaching, event management, sales, marketing, creating income streams, community building, website development, product development, networking, and more. My college degrees in computer science and mathematics seem like such baby steps with respect to all that I’ve had to learn since then. It often feels like I must continue to earn the equivalent of a new college degree every year or two just to keep up with the rapid pace of change, especially when it comes to doing business online. I always feel like I’m behind in one important area or another, and that pushes me to absorb and apply new ideas quickly.

It’s important to me to have the freedom to direct my own educational path. Every week I devour information, and the more I learn, the more I’m exposed to the naked edges of my understanding.

Lately I’ve been enjoying other people’s coaching programs. I belong to two paid communities at present and will likely join more. Learning this way is more expensive financially, but it’s cheaper time-wise because I can learn faster from experts and coaches than I can from just reading books. I love reading and typically go through about two books per week, but that isn’t what moves the needle forward most of the time.

I think that if I were an employee, I’d fall into the trap of being too comfortable resting on my existing skill set and not pushing to expand and deepen my skills every month. I think I’d spend too much time doing my work the same way over and over instead of questioning how I work and continually seeking to build relevant skills for tomorrow’s world.

Having so many economically useful skills makes it hard to fail since I can always pivot to one skill set or another. I can write articles or books. I can do public speaking. I can do Internet marketing. I know how to build websites, web traffic, and online communities. I can write software, plugins, or video games. I can do basic audio and video editing. I can do consulting or coaching. And so on. I don’t have to worry much about a shift in my field rendering my skills obsolete. In fact, I love it when shifts happen because it allows me to pounce on fresh opportunities before most people even know what’s happening… like when I got into blogging in 2004, the same year WordPress came out.

Developing a variety of skills has made me a faster learner too, so I’m able to quickly build competence in new skills and start using them productively. The more skills I learn, the faster I seem to be able to pick up new skills.

This constant pressure to keep learning can burn some people out. I’ve seen friends go through periods of overwhelm related to worries that they’re falling behind. I succumb to that feeling too sometimes, but overall I love the stimulation of pushing myself to learn, learn, learn. I love looking back on the past month or quarter and taking stock of what I’ve learned. This month I’ve learned a tremendous amount about creating membership sites since I’ve been studying that intensely, especially with the help of resources like Chris Lema and The Membership Guys.


The main emotions I feel when looking back on 25 years without a job are gratitude, appreciation, and relief. This wasn’t a smooth road, and I took some lumps along the way, but I’m really glad I decided to pursue a jobless lifestyle. That decision pushed me to grow in so many ways I doubt I’d have experienced if I’d gone the employee route.

When I think about the next 25 years on this path, I feel happy, excited, and optimistic. Even if I just keep living the way I am now, I think I’d be pretty fulfilled on this path. But I’m sure there will be many changes ahead, and I’m looking forward to navigating them, even if they throw me off balance now and then.

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