This book contains some of the most insightful and interesting comments made on the Hacker News website.
I'm going to go and replace 3 years with a "short time frame". Some things to focus on:
Market opportunity- a million dollars isn't a lot in the grand scheme of things, but it certainly is a lot if the market opportunity is not large enough. Even if you put Bill Gates and Steve Jobs as founders in a new venture with a total market size of 10 million, there is no way they could become too wealthy without completely changing the business (ie- failing).
Inequality of information- find a place where you know something that many undervalue. Having this inequality of information can give you, your first piece of leverage.
Leverage skills you know- You can go into new fields such as say Finance, but make sure you're leveraging something you already know such as technology and/or product. Someone wanted to start a documentary with me. I said that would be fun, but it would be my first documentary regardless of what happened. There was a glass ceiling due to that. If I do something leveraging a skill I know, I'm already ahead of the game.
Look in obscure places- We're often fascinated with the shiny things in the internet industry. Many overlook the obscure and unsexy. Don't make that mistake. If your goal has primarily monetary motivations, look at the unsexy.
Surround yourself with smart people- smart people whom are successful usually got there by doing the same and have an innate desire to help those do the same. it's the ecosystem that's currently happening with the paypal mafia and can be traced all the way back to fairchild semiconductor.
Charge for something- Building a consumer property dependent upon advertising has easily made many millionaires, but it isn't the surest path. It takes a lot of time and scale, which due to cashflow issues will require large outside investment probably before you are a millionaire. Build something that you can charge for.
Your metric shouldn't be dollars- If you're going after a big enough market and charging a reasonable amount, you can hit a million dollars. Focus on growth, customer acquisition costs, lifetime value of the customer, and churn.
Get as many distribution channels as possible- There is some weird sense that if you build something they will just come. That a few like buttons and emails to editor@techcrunch.com will make your traffic explode + grow consistently. It fucking won't. Get as many distribution channels as possible. Each one by itself may not be large, but if you have many it starts to add up. It also diversifies your risk. If you're a 100% SEO play, you're playing a dangerous dangerous game. You're fully dependent upon someone else's rules. If Google bans you, you will be done. Replace SEO with: App store, facebook, etc.
Go with your gut and do not care about fameballing- Go with what your gut says, regardless of how it might look to the rest of the world. Too often we (I) get lost in caring about what people think. It usually leads to a wrong decision. Don't worry about becoming internet famous or appearing on teh maj0r blogz. Fame is fleeting in the traditional sense. Become famous with your customers. They're the ones that truly matter. What they think matters and they will ultimately put their money where their mouth is.
Be an unrelenting machine- Brick walls are there to show you how bad you want something. Commit to your goals and do not waver from them a one bit regardless of what else is there. I took this approach to losing weight and fitness. I have not missed a single 5k run in over a year. It did not matter if I had not slept for two days, traveling across the country, or whatever else. If your goals is to become a millionaire, you need to be an unrelenting machine that does not let emotions make you give up / stop. You either get it done with 100% commitment or you don't. Be a machine.
If it's a "trend", it's too late- This means the barriers to entry are usually too high at this point to have the greatest possible chance of success. Sure you could still make a lot of money in something like the app store or the facebook platform, but the chances are significantly less than they were in the summer of 08 or spring of 2007. You can always revisit past trends though.
If you do focus on a dollar amount, focus on the first $10,000- This usually means you've found some repeatable process / minimal traction. ie- if you're selling a $100 product, you've already encountered 100 people who have paid you. From here you can scale up. It's also a lot easier to take in when you're looking at numbers. Making 1 million seems hard, but making $10,000 doesn't seem so hard, right?
Be a master of information- Many think it might be wasteful that I spent so much time on newsyc or read so many tech information sites. It's not, it's what gives me an edge. I feel engulfed.
Get out and be social- Even if you're an introvert, being around people will give you energy. I'm at my worst when I'm isolated from people and at my best when I've at least spent some time with close friends (usually who I don't know from business.)
Make waves, don't ride them- There was a famous talk Jawed Karim gave from youtube. He described the three factors that made youtube take off. I think they included (1- emergence of flash, so no codecs required 2- one click upload 3- ability to share embed). Find those small pieces and put them together to make the wave. That's what youtube did imho. The other guys really just rode the wave they created (which is okay).
Say no way more than you say yes- I bet almost every web entrepreneur has encountered this: You demo your product / explain what you're doing and someone suggests that you do "X feature/idea". X is a really good idea and maybe even fits in with what you're doing, but it would take you SO FAR off the path you're on. If you implemented X it would take a ton of time and morph what you're doing. It's also really really hard to say no when it comes from someone well respected like a VC or famous entrepreneur. I mean how the fuck could they be wrong? Hell, they might even write me a check if I do what they say!!!!! Don't fall for that trap. Instead write the feedback down somewhere as one single data point to consider amongst others. If that same piece of feedback keeps coming up AND it fits within the guidelines of your vision, then you should consider it more seriously. Weight suggestions from paying customers a bit more, since their vote is weighted by dollars.
Be so good they can't ignore you- I first heard this quote from Marc Andreessen, but he stole it from Steve Martin. Just be so good with what you do that you can't be ignored. You can surely get away with a boring product with no soul, but being so good you can't ignore is much more powerful.
Always keep your door/inbox open- You never know who is going to walk through your door + contact you. Serendipity is a beautiful thing. At one point Bill Gates was just a random college kid calling an Albuquerque computer company.
Give yourself every opportunity you can- I use this as a reason why starting a company in silicon valley when it comes to tech is a good idea. You can succeed anywhere in the world, but you certainly have a better chance in the valley. You should give yourself every opportunity possible, especially as an entrepreneur where every advantage counts.
Give yourself credit- This is the thing I do the least of and I'm trying to work on it. What may seem simple+not that revolutionary to anyone ahead of the curve can usually be pure wizardry to the general public, whom is often your customer. Give yourself more credit.
Look for the accessory ecosystem- iPod/iPhone/iPad case manufacturers are making a fortune. Armormount is also making a killing by making flat panel wall mounts. Woothemes makes millions of dollars a year (and growing) selling Wordpress themes. There are tons of other areas here, but these are the ones that come to mind first. If there's a huge new product/shift, there's usually money to be made in the accessory ecosystem.
Stick with it- Don't give up too fast. Being broke and not making any money sucks + can often make you think nothing will ever work. Don't quit when you're down. If this was easy then everyone would be a millionaire and being a millionaire wouldn't be anything special. Certainly learn from your mistakes + pivot, but don't quit just because it didn't work right away.
Make the illiquid, liquid- I realized this after talking to a friend who helps trade illiquid real estate securities. A bank may have hundreds of millions of assets, but they're actually worth substantially less if they cannot be moved. If you can help people make something that is illiquid, liquid they will pay you a great deal of money. Giving you a 20-30% cut is worth it, when the opposite is making no money at all.
Productize a service- If you can make what might normally be considered a service into a scaleable, repeatable, and efficient process that makes it seem like a product you can make a good amount of money. In some ways, I feel this is what Michael Dell did with DELL in the early days. Putting together a computer is essentially a service, but he put together a streamlined method of doing things that it really turned it into a product. On a much smaller scale, PSD2XHTML services did this. It's a service, but the end result + what you pay for really feels like a product.
Dig deeper, Sam.
Achievement-oriented people are given to depression both when they fail and when they succeed. If your identity is tied up in your work, then you feel bad about yourself when work isn't going well. That's obvious, and that's the message of this blog post. The implicit message is that you're depressed because you're not succeeding, so get your shit together and succeed and be happy like everyone else.
But then if you do succeed, you start to wonder, why did I just spend my youth in this masochistic, narcissistic path, and why the fuck am I not as happy as I was expecting, and is this really all there is in life. This is a classic "achiever in crisis." The problem is that you realize all along you've been doing things that OTHER people wanted -- that is, you've been doing things that make you valuable in society -- perfect summed up in the raison d'etre du jour, "making the world a better place." And nobody stopped you, because who can argue with making the world a better place? (Or being a doctor, or whatever.) But upon reflection, you quickly realize that this was in many ways easier than asking yourself what YOU wanted out of life. I.e. you've pushed aside your innate feelings and desires, whatever they may have been, and replaced them with the external motivation of achievement, under the rationale that you'd be able to "figure it out" after you had "made it".
Unfortunately achievers aren't really sure what they want "deep down" because achievement is inherently defined by society, and then after they've "made it" they freak out because they start to wonder if there even is a "deep down" or if they're just a highly educated donkey chasing a carrot.
If you talk to e.g. people who've gone through rigorous Ph.D. programs, you'll find a number of them were severely depressed after their defense. It was just kind of a let-down after such a long buildup, and then they started to wonder why they invested the entirety of their twenties into it and question whether that's really what they wanted their life to be. At least before the defense they could have something look forward to, and the various requirements provided a source of manic energy to propel the achiever forward.
Anyway I don't think the problem here is "not enough success," and I don't think the solution is having more coffee meetings. Founders need to take a hard look in the mirror and ask themselves why they're doing what they're doing and whether their depression is truly a function of their free cash flow or if there's a deeper dissonance between the founder's feelings and the expectations of society, i.e. the heroic mythology of the founder that Silicon Valley has been inculcating in susceptible teenagers for the last 20 years.
Just my 2c. I am not a founder just an observer and aspiring societal psychiatrist. If you want to learn more I highly recommend the book "The Wisdom of the Enneagram".
It looks a lot like astrological pseudoscientific trash but read it and see if things in it resonate with you.
Ok back to work.
Shiny things are nowhere as much fun after you get them as before, even if they have some value. So yes, that Kindle or iPad or whatever will have a real use, and you will be marginally happier with it than without, but not as much as you think
You can talk yourself into (or out of) anything. The only difference between smart people and other people is that smart people do this with bigger words and more complex arguments. Be confident, but also assume that you are broken in ways you can never spot. Find some ways to get a checksum on life decisions every now and then.
You don't need very much at all. Maybe a laptop computer and a couple changes of clothes. Pictures and videos of your life. That's about it.
Nothing will ever replace experiences. No matter how big the car, nice the house, or professional-looking the suit, it's never going to be as much fun or mean as much later as the experiences you have in life. And it's not just having the experience, it's looking forward to them, and planning them, and making pictures, movies, and blogs out of them. The best part, oddly, may be the planning. So planning a 200-dollar trip to the beach in the Fall with people you love may give you many hours of happiness this summer -- along with the fun of the trip itself.
Learn to keep picking topics and immersing yourself in them. Most everybody will say to drop out and become part of the system -- 9-5 job and TV/games/internet in the evening. If you want a life you could sleep through, that's fine. But if you want a life you can tell stories about, keep reinventing yourself. And that means constantly learning.
Lots of shit in life that once looked dumb or stupid opens up into this huge panorama of beauty once you learn the rules. In so many things you are like the guy who never saw a baseball game going to the world series. You kind of get it, but it all seems silly. You don't know the rules. Decide to learn how to appreciate music, for instance. Get a few college lectures on tape, get some good music to listen to, hang out with folks who are music connoisseurs. The more you know about various art forms, the richer your life is.
Forget philosophy and meaning-of-life shit. You're too young. For now, you are what you do. Go do something worthwhile
Stick to a daily exercise routine at all costs
If you are changing and getting better, that means you are changing friends too. This was very difficult for me, but you can't hang out with the same folks and expect to become a better person. There are exceptions, of course, but to a large degree your life is controlled by whom you choose to be friends and hang out with. Be aware that you don't want to be the same person at 30 as you were at 20. I'm not saying be an asshole -- keep being friendly by all means -- but be very careful who you hold yourself up against as "normal"
Dating is a numbers game, like a lot of other things. Learn the skills of dating and don't sweat picking up chicks (or guys)
Concentrate on your weaknesses. Make them stronger. When you get to your 30s you can work from your strengths, but there has to be some time in your life to work on shit you suck at, and for me it was when I had the most motivation, my 20s.
Speaking of which, you have to learn management. No matter what you do, there will be a manager. Even if you don't want to be one, you have to understand what the job is like to help out your manager. Being a good leader means being a good servant. This concept sounded easy (or facile) to me in my 20s, but proved hard to apply in practice.
You are never ready for kids. Have them early while you have energy. Read all the books about kids if you must, but realize that creating a replacement is about the most biologically easy thing you could do. After all, evolution has been working on making you a great gene transferral and primate-raising machine, so don't get paranoid and neurotic about all the latest parenting fashion. Use some sense.
Everybody wants to be a rock star and win the lottery. Nobody ever does, and the ones that do end up destroying their life. Realize slow success is a million times better than overnight success.
Much of the stuff in life that normal people do is geared around killing time by distracting you with shiny things of no value. You may never be able to fight this completely, but you should at least deeply understand it and how it affects your goals
Create. With a passion. There are two major kinds of people in this world, consumers and creators. The herd will push you to consume, life will push you to consume, consumption is the easy and default path, but true joy and a full life come from creating. It does not matter one bit how many people like what you create, just create. Write. Blog. Make videos. Make a movie. Write a program. The longer the format and the more creativity involved, the more you are going to turn on and exercise key parts of your brain. Nobody wants to be 80 and only have stories of being at the office, but fuck, if you were at the office creating something at least you tried to make a difference. I'd rather be that guy than the one who watched Sumo wrestling everyday (or played 20,000 hours of WoW during his 20s) The only thing you're going to have at the end of your life are the decisions you made, the things you created, and memories. Learn to maximize these things.
I felt obliged to comment because I feel I know what you are talking about and I also worry that much of the advice posted so far is wrong at best, dangerous at worst.
I am 42-year-old very successful programmer who has been through a lot of situations in my career so far, many of them highly demotivating. And the best advice I have for you is to get out of what you are doing. Really. Even though you state that you are not in a position to do that, you really are. It is okay. You are free. Okay, you are helping your boyfriend's startup but what is the appropriate cost for this? Would he have you do it if he knew it was crushing your soul?
I don't use the phrase "crushing your soul" lightly. When it happens slowly, as it does in these cases, it is hard to see the scale of what is happening. But this is a very serious situation and if left unchecked it may damage the potential for you to do good work for the rest of your life. Reasons:
The commenters who are warning about burnout are right. Burnout is a very serious situation. If you burn yourself out hard, it will be difficult to be effective at any future job you go to, even if it is ostensibly a wonderful job. Treat burnout like a physical injury. I burned myself out once and it took at least 12 years to regain full productivity. Don't do it.
More broadly, the best and most creative work comes from a root of joy and excitement. If you lose your ability to feel joy and excitement about programming-related things, you'll be unable to do the best work. That this issue is separate from and parallel to burnout! If you are burned out, you might still be able to feel the joy and excitement briefly at the start of a project/idea, but they will fade quickly as the reality of day-to-day work sets in. Alternatively, if you are not burned out but also do not have a sense of wonder, it is likely you will never get yourself started on the good work.
The earlier in your career it is now, the more important this time is for your development. Programmers learn by doing. If you put yourself into an environment where you are constantly challenged and are working at the top threshold of your ability, then after a few years have gone by, your skills will have increased tremendously. It is like going to intensively learn kung fu for a few years, or going into Navy SEAL training or something. But this isn't just a one-time constant increase. The faster you get things done, and the more thorough and error-free they are, the more ideas you can execute on, which means you will learn faster in the future too. Over the long term, programming skill is like compound interest. More now means a LOT more later. Less now means a LOT less later.
So if you are putting yourself into a position that is not really challenging, that is a bummer day in and day out, and you get things done slowly, you aren't just having a slow time now. You are bringing down that compound interest curve for the rest of your career. It is a serious problem.
If I could go back to my early career I would mercilessly cut out all the shitty jobs I did (and there were many of them).
One more thing, about personal identity. Early on as a programmer, I was often in situations like you describe. I didn't like what I was doing, I thought the management was dumb, I just didn't think my work was very important. I would be very depressed on projects, make slow progress, at times get into a mode where I was much of the time pretending progress simply because I could not bring myself to do the work. I just didn't have the spirit to do it. (I know many people here know what I am talking about.) Over time I got depressed about this: Do I have a terrible work ethic? Am I really just a bad programmer? A bad person? But these questions were not so verbalized or intellectualized, they were just more like an ambient malaise and a disappointment in where life was going.
What I learned, later on, is that I do not at all have a bad work ethic and I am not a bad person. In fact I am quite fierce and get huge amounts of good work done, when I believe that what I am doing is important. It turns out that, for me, to capture this feeling of importance, I had to work on my own projects (and even then it took a long time to find the ideas that really moved me). But once I found this, it basically turned me into a different person. If this is how it works for you, the difference between these two modes of life is HUGE.
Okay, this has been long and rambling. I'll cut it off here. Good luck.
Here are a few tips that have worked for me to achieve the desired kind of big picture awareness and mental state suitable both for flow and for strategic thinking:
keep a simple per-project todo list (I use a text file that I edit with emacs in text mode, one item per line. Delete when finished).
realize that if you are procrastinating it might be because part of your brain disagrees with a decision you have made. Reflect on the decisions and uncertainties you feel, and let any objection come to the surface of your consciousness. Often the remedy is pretty quick and the procrastination disappears.
escape the echo chamber. Maybe some people in your life are reinforcing stupid decisions or criticizing good ones. Be brutally honest with yourself and believe in yourself. Seeking social validation is in many ways a crutch.
environment matters (people, architecture, city, flat, office, etc.). Be picky and find one that gives you the right mix of ingredients for productivity, inspiration, and happiness and doesn't make you feel bad about yourself, discouraged, etc. It may be very different than what works for other people or what is trendy.
Even if you think university will teach you absolutely nothing, you've got a one-time offer from society that we're going to subsidize anything you do for the next four years and not have any expectation that you'll work for a living during that time. This offer is essentially only good once. Take it.
That said, you can learn an awful lot from school. You say it is tedious -- that suggests to me you're underchallenged. Have you tried learning a foreign language yet? Like, really learning a foreign language, rather than learning to say "Yo quiero una cerveza" like I assume your high school Spanish has taught you? It is incredibly rewarding, in all possible senses of the term rewarding, and you'll never get a better opportunity than the next four years. (Dedicated instructors, plenty of time not occupied by the demands of job and family, social push to complete studies, possibility of study abroad bankrolled by someone else and unrestricted by visa concerns, etc etc etc...)
You can also learn quite a bit about programming during college, even if actually doing it is a much better teacher. (Although, again, we're subsidizing all your activities for four years -- you show up for 3 hours of classes 5 days a week, the rest of the time is yours, program as much as you want to program.)
Incidentally, I hate to sound like An Official Adult, but just trust me on this one: the job market for young Americans sucks right now, and you absolutely do not want to be facing it without a degree. Degrees are not just for boring megacorps coding Blub: even cool companies which code Lisp look for people who can carry tasks to completion, and not possessing a degree when we hand them out like candy on Halloween suggests "I am insufficiently motivated to do clearly beneficial things when they require non-trivial amounts of actual work. Please employ me -- you will find me excellent at everything you assign me to do, provided none of it is actual work."
A few things to remember: You're much more valuable than your first employers would have you believe. Don't let that go to your head. Do go to university. I know how eager you are, having been in that position myself, but it's a mistake to drop out of one of the most effective social networks ever devised by humankind. Go for the social experience and the social doors it opens.
If you're still not convinced, take a hard look at the background of all of the YC partners and realize that all of them seem to have attended some good schools. While you can make it without university, and you can lead a happy life and do whatever you want and be in the upper 1% of quality of life across all of humanity without attending university, you only get one chance to choose not to follow "The Path," which is high school -> good university (undergrad) -> better university (graduate student) -> learn how to be around rich people and convince them of your way of thinking. Normal people who don't attend university simply don't get this opportunity. Specifically, the opportunity to test out what works and what doesn't, socially, with wealthy people. Why is this important? Well, if you want to do something big, and you don't have any money, wealthy people are by definition the only ones who can help you. Even at absurdly high salaries, it's very hard to save up money to do something that involves hiring other people. Possible, but difficult. So where do you turn? Investors, of course. Except, crap, they're wealthy, and you have no idea how to be around them as equals. But wait, you attended university, and so maybe they have some shared ground with you... Hm, nope, you didn't. Well, of course, your website demonstrates traction, and traction is what matters to an investor. But what else do investors care about? Your team. Where (or whether) you went to university says a lot about you, fortunately or unfortunately.
Really, there's no reason not to go. Make some reasonably intelligent decisions and you'll have a great time while getting the debt paid off in a reasonable timeframe.
But if you don't go, you may find you'll want to later but never really get the opportunity. Not in the way you once had. Once you depart from The Path, you'll have to beat your way back onto it, surmounting bills and work and all kinds of annoying stuff that people fresh out of highschool don't really have to worry about just yet.
Speaking of bills and debt: whatever you do, don't get into credit card debt. Don't get into credit card debt! I can't emphasize this enough. It's so tempting, but just don't.
Do use a credit card though. Just pay it off every month. Otherwise you may not be able to get services (internet, phone, whatever) at a new apartment, or buy a car. Had it happen to me once, and it sucks. No credit history = unknown risk = "I'm sorry but we will never do business with you."
Kind of an awkward place to end a ramble, but whatever. Maybe some of the ideas might be useful.
Maybe consider leveraging this particular experiment to help you attend one of the local top-tier universities as an undergrad. Ask people if they have any advice on this, and maybe you'll find someone who could help with the admissions process. Who you know matters more than what your highschool history was like, so maybe some strings could be pulled somewhere.
A little hypothesis:
Burnout is your subconscious's way of telling you that you're on the wrong track.
I've found that every time I've felt burned out - whether in writing, coding, startup, life - it's because I was working on something that ultimately was going nowhere. I needed to revisit my assumptions, yet my conscious mind didn't know that. Burnout was a way for my subconscious to say "This isn't going to work, you're not working on the important stuff, take a step back and look at the big picture."
When writer's blocked, I delete the last 3 paragraphs I've written and take the story in another direction. This has almost always cured my writer's block; when it doesn't I delete the last page and take the story in another direction.
When coder's blocked, I revert to my last svn commit and start again, usually with a smaller task. I've thrown away up to a week's worth of work this way, which is another lesson: commit early and often. Commits should be an hourly or minutely process, not something you do after a whole bunch of work.
When blocked in general, I think about the last design decision I made and revisit. Oftentimes, if I'm blocked entirely and can't even get started on implementing a feature, it's because the feature is ill-conceived and needs to be redone. Maybe it's done with incorrect assumptions about how users will use the problem, or maybe it just doesn't serve any purpose. Revisit whether you need the feature at all.
If you find you can't work on your startup at all, maybe it's a sign that your startup is on the wrong track. Revisit your idea. I'm actually at that stage with mine: we scrambled to get a demo ready for YC, but now that I want to procrastinate and avoid work (our market is people who want to procrastinate and avoid work), I find that I don't want to use our product. But I've got some ideas about how to backup and try a different approach, and now I want to try them out and see if they can get me procrastinating with the startup itself.
So, here's my story; I tell it occasionally when stories like yours come up.
I had no college experience, but did manage to jump right in to a good I.T. job while I was still in high school, and from there into an even better I.T. job in another state where I made more money than I knew what to do with. (I've never been good with money, and didn't understand what "savings" meant.) I worked there until suddenly one day I went on a camping trip with family, came back, and decided I hated computers. I quit that job, and the industry.
Then the dotcom bust happened.
So, at about your age, there I am, living back with my parents. They at least were supportive, but it took me a while to get my feet back under me. I took some simple jobs, took up rock climbing as a hobby, eventually became a climbing instructor, learned a whole bunch of skills but got paid next to nothing.
Eventually all of the credit I had amassed during my previous life in I.T. ran out, and I was deeply in debt with not enough income to manage it. My parents had moved away, and I ended up moving with them. Again.
Not my proudest moment.
It took months, applying to nearly every job and place of business in the area, but eventually I got a simple retail job. I lied about my past experience so that they wouldn't tell me I was overqualified to operate a cash register.
I let my bank accounts and credit fall apart. There was nothing I could do about it but start over. So I did.
Eventually, I was ready to re-join I.T. and happened by dumb luck across the perfect job opening for me -- about 6 hours' drive away. I patched up my car enough to get me there, and took with me the bag of spare change I had accumulated over a year or so.
The boss and I hit it off, and I got the job. It was one of the most challenging jobs I've ever had -- I was a one-man I.T. department for a store & restaurant that had no budget for anything fancy. All patchwork, all the time. I had gotten pretty good at that by then.
I was homeless at that point and my car barely got me there, but I happened to have some friends in the area so I stayed on their couch and made up for it by cleaning while I was at home. My first paycheck got me living expenses, the second got me the new radiator that my car needed, and so on.
Several years later, I've gone through a couple more jobs (a step up each time), started my own business, my credit is slowly rebuilding, the business is supporting two other people. It's still a struggle every day, but it's an uphill struggle. Every year is better than the last.
So, if your friends are giving you a hard time, tell 'em to knock it the hell off. Or find new friends. You've made a mistake -- maybe, you won't really know for sure for years -- but you have an opportunity to gain experiences that others never will. If I had never been a climbing instructor, I never would have developed the people skills that I needed to be an effective manager, let alone a business owner. You don't know what the future holds, so there's no sense in admitting defeat yet.
I won't try to lie to you, the next few years could be rough. Real rough. There could be an awful lot of days where you don't want to get out of bed, you don't want to do anything. Depression certainly doesn't make it any easier -- I know that from experience, too. But, if you keep trying anyway, you may discover that your best days are ahead of you yet.
Also, you're really not an idiot. People that never take a risk rarely end up in great places in life. You took a risk, it hasn't worked out so far. But, you didn't know what was going to happen before you did it. An idiotic decision is one that you know is bad when you make it. Unless you have an unusual power of foresight, you're not an idiot for making the decision you made.
Keep working on the freelancing. Keep getting better, keep making connections with other people. You have to become very aggressive now; it's not like a regular job where somebody else is doing the marketing and management for you and setting a schedule. Learn to start recognizing little victories. If you made enough money this week to pay a bill that you couldn't pay last week, that's a victory. Learn to get good at operating within razor-thin margins. Make sure you take a real hard look at all of your expenses; people that aren't accustomed to this style of living often have expenses that they believe they must have. At one point, my expenses were literally: food, and gas for the car. And that was it. I had no bank account, I got my checks cashed at the grocery store, I kept the cash in my wallet with a little extra hidden at my crash space (because paranoia), and so I knew exactly how much money I had to spend and live off of. If I had an extra $20 come payday, that was a real good week.
If you're lucky enough to be in an area with good public transit, ditch your car. Those things are money sinks. The moment you can't afford your insurance or registration, you will get pulled over. It's like magic, really bad magic. And the fines and fees just pile up, and there are no sympathetic ears when that starts happening.
Let go of everything that you think you have to hold on to -- your sense of importance, of self-worth, anything that might be holding you back or keeping you from making the hard decisions that have to be made -- and just decide that you'll buy it all back later.
Then just take your life one day at a time for a while.
I am crippled by the feeling that it's "too late". ... I can't help but feel that if I had started in earnest at 25, at 21, at 19 — then maybe the list of accomplishments at the end of my life will be longer.
Too late because you're 26? More like too early. The way you deal with the gnawing in your chest is to correct your view of success with a healthy dose of reality. The 21 year old success is almost exclusively a lie, little more than a media fabrication; don't buy what they're selling.
Here's a nice list, and the age at which they got their big hit: