Let's talk about how to live your best life today.
Lately I've noticed an uptick in comments from people, usually in their teens and twenties, asking things like, "How do I get your life?"
Usually I make a throwaway not-a-joke about going through a lot of misery first.
But I think this is perhaps unkind, because while a self-effacing joke is fun (and true about how I got here), I think the question is often asked very earnestly by people who wish they could change their circumstances.
I empathize. This was me throughout my 20s.
While the winding, misfortune-fueled road did bring me here, it would have been nice if I could have been more intentional about my path with the guidance from someone who had walked it... this was not an option for me.
So I feel like I should do better than a throwaway joke.
The point I'm usually trying to make with the joke is that it wasn't easy. Going through a gender transition, having two failed marriages while I sorted myself out, and spending 15 years in the corporate grind were all experiences that taught me important lessons.
And you may need to walk a similarly winding road for a while to get to where you want to be.
After all, it's very much about the journey. That's one of the big things I'm still learning every day.
You have to learn to love the journey itself.
My advice for how to reach a similar point ON the journey to where I'm at would differ depending on what aspects of my life you find enviable and where you're at today.
But boiling down the essence of my advice would probably look like this:
"Anything is possible. Go try."
Fifteen years ago the idea that I would have happily transitioned, founded two companies, have written scores of books, and be working on whatever projects I wanted every day while I drive around the desert in an RV (studying magic) would have seemed utterly impossible.
When I take a step back and think about the core thread of these activities, it comes down to freedom (both personal and financial) and flow (engagement with creative pursuits I find fulfilling).
So how do you actually achieve freedom and flow in your life?
Step one is intentionality. If your ideal life is different from your present life, nothing is going to move you toward your ideal without recognizing that your current situation needs to change.
You don't necessarily need to know exactly where you're going.
"Not here" is fine as a first step. In fact "Not here" IS the first step toward defining, "Where then?"
But you need to know where you are (at least) to map out your options to get wherever it is you'd like to end up. Obtaining freedom isn't cheap or easy.
People who say "follow your bliss" are misleading you. This is dumb if your bliss won't actually give you the tools to move yourself toward freedom and flow.
You need to build skills and tools that increase your degree of access to these states.
And I will warn you up front that freedom can be very scary. Taking ownership of your destiny means that you're responsible for your destiny.
Until this point, it's easy to hunker down and pretend that it's society's fault you don't have the things you want.
But also NOTHING has ever made me feel more alive than taking interesting, calculated risks and figuring it out along the way. Those are the times in my life when I've felt most alive: When my RV breaks down in the middle of nowhere and I just have to solve the problem.
This is the core of the adventure experience. You go out, do something hard, and test yourself. You don't always win. But you get back up, lick your wounds, ask yourself what went wrong, and try again.
The only way to lose at this game is not to try again.
So let's get specific and talk about increasing your degrees of personal freedom, financial freedom, and flow access.
Let's do financial freedom since it's arguably the easiest of the three. You want to do whatever you want (within reason)?
There are two elements to achieving financial freedom: Income independent of an employer and reduction of fixed costs of living.
Debt is a killer here. Do everything you can to shed debt. I've been a fanatic about avoiding it forever because it's anathema to freedom.
You need less than you think you do to get by. My grandpa taught me this. Whenever you go to buy something, ask yourself, "Do I need this as much as I want to be financially independent?" This is especially true of large purchases. You can always learn to be happy with less.
Fixed costs of living in general are the other big one. You need cash to make things happen. Anything you can do to reduce your rent burden or your monthly bills is a step in the right direction. Live with your parents. Share rent. Buy an RV and live in it ($12k is enough).
If your reaction to this advice is "But what will people think when they find out I live in a trailer/with my parents etc etc," you don't want it badly enough and definitely aren't ready for personal freedom.
If you actually do want to emulate that aspect of my adventure, RV life, I've already written a long article about that. You too have the ability to go live in a van by the river.
But even with an RV most people will be tethered to a job--remote work or not. You're not REALLY free if your boss can call you at 7pm and ask you to jump on a conference call real quick, and it's going to be stressful if you're in nowhere Arizona without solid internet.
And of course this assumes you're fortunate enough to be able to find a white-collar remote work job in the first place. Not everyone has ability or access to do this.
Fortunately, the path out is available to everyone. You have to build your own income sources.
When people talk about doing this, it sounds both tantalizingly easy and impossibly hard at the same time.
I remember being 27 and coming home from work to brainstorm business ideas on a whiteboard and being SO frustrated by how hard it was to think of something.
In the oughts, the "four hour workweek" strategy was a bestseller about building a dropship vitamin business to free yourself from work.
This is only a partial truth. I have never worked harder than I do right now for myself. But my self-directed work is very satisfying.
Ironically, many of the skills you need to make a self-directed career easier are things you pick up fastest in a conventional white-collar setting (because you need to manage your business). But anyone can learn on the fly if you're smart and determined.
The core skills you need to have to build independent income streams are 1) making stuff and 2) selling stuff.
#2 is more important than #1 and you can practice it with almost anything. The best way to learn to sell stuff is just to try. Craiglist. Fiverr. Start selling.
You don't have to be a maker today to start. Get creative. You can go to a used bookstore, buy books of art for less than $10 and some frames at Walmart, and cut pages out of the books to frame. Start a little store on OfferUp and see what people will buy.
This hones your selling instincts and will start to teach you about marketing because you'll intuitively learn what's appealing and what isn't based on what you're moving.
Longer term though, I recommend making things that scale better.
Whenever you're thinking about what you can sell, you have to think about it in terms of revenue as a function of effort. What this means is "how many hours does it take to generate $1 from this effort after costs of materials are considered?"
Something I didn't fully appreciate until I worked at a firm that sold data was the true power of scale offered by digital or soft assets. If you build a house or a painting you can only sell it once. If you write a book or code a program, you can sell it thousands of times.
This doesn't mean that physical assets are necessarily bad to sell! But if I was laying the groundwork for a long-term plan from scratch, I'd be looking for ways to build assets I could create once and sell ad infinitum.
From this lens, traditional jobs are a very bad deal. You're selling your time in one hour blocks and getting a fixed fee in return, while someone else claims the future value of your labor. This might be worth it if you're building key skills, but you want to move on fast.
Also, if you build digital assets you retain, you can remix them endlessly into other projects. The fantasy world for my first novel is now serving as the base of my game. Stock art assets I got from a promo deal get remixed for all kinds of graphics I need.
This brings up another point which is that you don't necessarily have to sell stuff YOU make. That's what learning to sell teaches you: You can pay someone else to build things and sell them more effectively. This is literally what business IS: channeling labor effectively.
You want a free business idea? I've spent $200 in the last week on itch.io and GameDevMarket.com. There is a lack of high quality asset packages. You can pay artists on Fiverr to paint you assets and package them into small sets to sell there. Boom.
The point I'm making is that opportunities like this exist all over the place and the only limit is your own creativity and your ability to recognize needs people have. Make enough things available to sell and people will buy some of them.
That's the other part of this: I don't make a ton of money on any one asset. I have tons of books, several Patreons, and several small digital products out there that all generate small monthly income streams that add up over time. The more you make and sell, the better odds.
I don't want to hammer on this point any more because I've already written about this a lot. I recommend reading my whole set of writing articles for more advice on building a biz.
The other thing reducing your living expenses and building independent income streams offers you is key to accelerating all of this: You get time and disposable income.
People say "you need money to make money." This is true but not in the defeatist way it's usually said.
You don't need a LOT of money to make money. It's just that the more disposable income and recurring revenue you have, the more options you have to channel that into new ventures.
Playing WoW taught me this. You can own a chunk of the in-game economy with some effort.
And you don't start by buying the super-expensive high end toys that are hard to move. You start by building an economic base by flipping cheap stuff you can afford and grow over time. Soon you have assets AND a bankroll.
Ironically, playing the economy in an online games is actually a GREAT low-risk way to learn to sell. If you have no real-world option and are currently addicted to an MMO, do this. At least you'll be building good selling instincts and learning to manage cash cheaply.
As you build your income streams and have more access to revenue, you can experiment more without risking anything major because it'll keep trickling in. I pay for TextSpark's burn rate and my game art with my publishing biz. I have time to work on them for the same reason.
And it's all low risk because I paid cash for my RV and my costs of living are STUPID low because I've intentionally structured my life that way. This allows me to do small business experiments all the time. This allows me to fund magical research. This lets me do whatever.
You want to build a stable of assets that grow over time and put yourself in a position where you can continue to add to them, not get burned if something fails, and be patient because things don't HAVE to succeed over night. They won't, I promise.
And you have to keep going and not get discouraged. Small successes today are the start of a snowball rolling downhill. You'll look back in five years at what felt frustrating now and marvel at how it grew with consistent effort.
Okay, basta. Let's talk about personal/social freedom. Getting this is easier once you have financial freedom, because you're no longer dependent on the approval of others for financial support (your career).
But it's still a double-edged sword.
Personal freedom is even more terrifying than financial freedom because it means having to reject the impositions and expectations that other people have about how you should be living your life and following your own moral and personal compass.
This can be very, very painful if the people around you withhold love and support conditionally on taking actions that they approve of. I am very lucky in that my family and friends have tended to support my personal happiness regardless of actions I take.
But this is only partially luck. Finding your tribe--people who respect and support you in your endeavors--is totally within your control. If your friends don't support your dreams, they suck. Get new friends.
Often when friends or family try to hold you back from going after things you want, it's presented as being concerned about your well-being. This is _sometimes_ true. But more often, people holding you back do so because of their own fears and limiting perceptions.
When people tell you "artists don't make any money," or "most businesses fail," often there's an element of comfort in this belief because it absolves them of the responsibility and regret of not having chased their own dreams.
Don't listen to them. You'll never succeed if you don't try.
Look, you WILL fail. I promise.
But it's not something to be afraid of. The thing people don't realize is that "failure" isn't the end of the game. It's a NECESSARY step on the journey to success.
This is literally the try/fail cycle you see in almost every book. Okay, so you try to do something and it doesn't work out. Did you learn? Cool. Try again. That didn't work? Maybe the 3rd or 4th thing works out for you! Maybe the 5th.
The thing is that you now have a personal "failure" rate of 80% (gosh, those odds suck, right?)... except that you're laughing all the way to the bank because your artistic project is finally working out and you're living off your art because you didn't give up.
Choosing personal freedom means being willing to go against the grain of what other people think you should be doing in order to pursue a strategy that moves you closer to the life you envision for yourself. This may cost you friendships and relationships.
You're the only person who can decide if those relationships are worth the cost to you. But if you want something and are building toward something important to you, you need to surround yourself with people who support and encourage you even if others don't understand.
Personal freedom means willing to step back and be resolute in saying, "No, I want this. It's important to me. I might fail. It's worth it to try anyway. And you can't stop me from trying.
This might even be dumb if you're unwise. And yet it's the only way we learn.
I'm not advocating foolhardy decision making here. Your risks need to be calculated. But often you don't have information that you can only get through experience. Try/fail cycles yet again. In an effort to protect us, sometimes the people around us try to limit us.
Taking responsibility for your own destiny and obtaining personal freedom means trusting your own judgment in who to listen to and how to act in ways that may go against the advice of those around you who are not on a similar path.
Talk to people living the life you want.
People living the life you DON'T want are not going to be able to give you as good of advice on how to do something different than people living the kind of life you want to have. It's your life. You only get one. You get to choose how to live it.
This isn't a dig on just following the advice of your elders and taking a conventional path! That works really well for a lot of people and makes them super happy. I'm happy for them.
But this is a thread about obtaining personal freedom outside of that framework.
If a conventional life makes you really happy, you probably wouldn't have bothered reading the last 62 tweets in this thread. Still, it's worth thinking about (yet again) what you really need to be happy--understanding and identifying where you want to be. Know thyself.
Finally, there are degrees of freedom from obligation you can obtain that don't involve an all-or-nothing rejection of relationships that get in your way. This is called "establishing boundaries."
Being part of a social framework is being human. Even on a compound in the desert, you're not totally free of obligations... ever. Even like-minded friendships always impose some responsibility on you. This is good, though. You need other people. People are great.
So choosing personal freedom means you choose the degree of obligation you'll accept from your relationships and drawing clear boundaries.
"I love and respect you, but I want X and you won't talk me out of doing it" is a powerful statement.
This can be very scary. What if you're wrong? What will they think if you look stupid when you fall on your face? Won't that be embarrassing?
Yes, it will. But who cares? Do you want the thing you want or not? Eat some dust and get back up.
Finally, let's talk about flow. One of the things I've learned is that I do my best work when I'm working on whatever I'm excited about on any given day because I can pour my passion into. I work an average of 16 hours per day and I love almost every minute of it.
This is my personal flow state. Whenever I deviate from this pattern, by forcing myself to grind through stuff I'm not excited about, my work (and mood and confidence) suffers for it. You have to find your own pattern.
Because I've built my life around personal and financial freedom, this is no big deal. It was much harder when I had a fixed 9-5 with fixed expectations and deadlines and less control over my projects.
But I'm SO much more productive now then I ever was then.
Finding a way to unlock your flow state is the key to unlocking your potential to make really awesome things. When you feel engaged and motivated, your odds of success and commitment to a project go way up.
This will differ for everyone.
But a thing you can do to enhance your flow state once you know what it looks like is find ways to not do things that yank you out of it. Money is a flow lubricant here. Paying other people to do the things you hate that break your flow offers massive returns.
And also you need to let go of all of your "shoulds." When you feel like you "should" be doing something a certain way and this differs from how you enjoy doing it, it will create dissonance for you. It's not in alignment with your real emotions and preferences.
For a long time I struggled with the idea that I should work on one project until it was done and then pick up another project. I kept bouncing between projects and getting discouraged that I never finished anything and beating myself up because I "wasn't doing it right."
What was extremely helpful for me was giving myself permission to pick a set of priorities (in my case 3-6 projects) and telling myself I didn't HAVE to work on any of them, as long as I worked on ONE of them on any given day. This aligned with my personal preferences better.
What this means is that I reach individual milestones more slowly on my projects, but I make better progress on all of them overall than I would trying to grind them out and abandoning them due to burnout and boredom.
Fits and starts work for me. Slow grind does not.
This goes against "conventional wisdom" that you should focus on one thing at a time... but in my case, recognizing that the conventional wisdom was making me unhappy and I STILL wasn't finishing anything was the key to finding a work style that DID work for me.
Because I've started letting go of ideas about how I "should" be working, I'm able to stay in my flow state and crush my goals. I paused my game and worked feverishly on TextSpark for six months. Got it out the door.
Now I'm back to working on my game and my publishing business, magic research, and TextSpark are taking a backseat at the moment. I touch them, work on them a bit, but they're not my focus this week.
I made space for myself for this to be okay and I'm in near-constant flow.
Your pattern will look like whatever it looks like, but you need to pay attention to your emotional state and think about how you feel as you pursue different activities. Let go of "I should be doing X" and just observe. Then build channels toward feeling happy and engaged.
Finally, in addition to doing the things I've already talked about, there's a few tips that make all of this stuff easier. First, having freedom means taking responsibility, and you need to be comfortable with learning and trying stuff. Mistakes don't help if you don't learn.
You need to get better at learning, which means building accelerator skills to improve learning and retention.
Also, many people tell you to get very specialized at something. This is good advice, but I'd rather be in the 75th percentile at many things than in the 90th on one or two things. Ideally you can have both, but personally I prefer the former if I only get one.
This is because as an entrepreneur (or even just free-roaming person following their flow) you encounter many situations where a diverse set of skills is useful. If you're hyper specialized, you have to pay someone to help you.
If you're a solid generalist, being in the 75th percentile at lots of things is more than good enough to deal with the majority of situations that come up. In fact, it makes you a better judge of how not to get grifted when you DO need to hire someone for a 90th % task.
And building more generalized skills ironically makes you better at everything you do, because you can cross-apply patterns and tricks from different disciplines and see things you didn't notice when you were more limited in your focus.
Coding makes me a better writer and writing well makes me a more structured coder. Artistic skills make me a better marketer, and marketing improves my emotional awareness and understanding of psychology. That makes me a better friend, which opens more opportunities to me.
There are a million examples of this. You should always be challenging yourself and learning new things. They all make you better. Ideally you're learning things that complement one another, but even things that seem like they don't help you in surprising ways.
As for hard skills to start with, I recommend skills with broad application. You literally can't go wrong with being a better communicator (written and spoken). This makes everything easier.
And I HIGHLY recommend learning to code. Even just the way it organizes your thoughts helps you structure things more clearly and appreciate systems better. Systems thinking offers MASSIVE returns for business minded people because you see opportunities to connect value.
Making high-leverage products that you can sell ad infinitum usually involves either writing, coding, or selling in some capacity. And systems thinking helps all of them. If you want a solid springboard, those are the ones I'd start with. (I'm biased, that's my skillset.)
Lastly, I'm gonna bring you back full circle to what I started with: You simply don't know what's possible for you until you try. People will always tell you you can't succeed for reasons. They might be right. They might not.
Listen, think, and if you want it, go try anyway.
The only way to be absolutely sure you can't find your way into something you want very badly is to not try at all because you're scared of failure.
People will also say this is a lie and survivor bias and it misleads people into wasting time and effort.
This is not true.
It's only a lie if you try for a while, give up, and haven't gained or learned anything in the process. In practice, this almost never happens and the journey itself changes you.
You either learn valuable things about yourself that allow you to find your way to success and the life you wanted, or you discover things that change your preferences and feel your way into a life that does satisfy you. Either way it's an important journey.
So how bad do you want it? Do you want it badly enough to stomach failure? Embarrassment? Toil on the path?
All you really have to lose is your life. Almost anything else you can find ways to recover from.
Go get what you want. Don't let anyone stop you.