Achieve Escape Velocity: Failing to Freedom by Failing Forward
- Waylon Bennett
- Aug 12, 2024
- 10 min read
Updated: Mar 12
You make $50,000 a year? Not knowing how to make a million is costing you $950,000. This is the cost of ignorance, a tax everyone pays.
After an overtime shift put me at 74 hours for the week, I sat searching for a better life in the stained upholstery of my beat up used car. I sat as the parking lot emptied, waiting for the AC to cool the summer air. When I found myself alone, looked down and saw the salt from my sweat crystallizing on my slowly drying pants. I wondered if there was a better way. I wiped fiberglass out of my eyes with my cleanest dirty fingers and it burned about as bad as I expected it to. I used the moisture laden hem of my shirt to rub at them next, and the saline gave me tears for my trouble. Years later, things were different, but they hadn't really changed. I still felt like I was in the wrong room - not special, just out of place. About seven years on I got a bone thrown my way after being laid off and made more substantial money at a federal contract job, more than I'd even thought to expect, but it was a feast foreshadowing famine. The contract was renegotiated a few times, and as perks I had enjoyed went away eventually it expired. My savings depleting rapidly, I was on the hunt for where I'd dirty my cleanest fingers next.
One day almost two years into my next factory job, my little girl yelled "Dada" for the first time and cried at the top of the stairs as I walked out the door to head to work. When I got to the car and sat there, unmoving and still hearing her wail behind two closed doors, I was reminded of that day in the car all those years ago... But this time, I had no sweat or fiberglass to blame for the tears that welled up but didn't fall, and her cries set my soul on fire. This blog serves to document whatever happens next, and this post in particular showcases some of the thoughts and content I consumed that have already begun changing my life. I hope they help change yours, too.
Tip #1 - Traits of Successful People
You stay in poverty until you learn the first lesson of poverty, which is two words: my fault.
The most successful people, and I mean the .001% here, have three traits in common.
A superiority complex
Crippling self-doubt
Strong impulse control
Relentless drive goes without mention, and whether they push so hard because they think they deserve more, or that they're just willing to sacrifice anything to get it, they think they're better in some way than the people around them. At the same time they tell themselves they're going to achieve so much, paradoxically, they have doubt gnawing at them, making them question if they're even good enough for the success they're convinced is theirs for the taking. These work together to convince them, for better or worse, to keep going no matter the sacrifice. So, they have something pulling them, they have something pushing them, and on top of this they have a laser focus that comes from their ability to control their impulses, limiting distractions until they reach their goal. How about us commoners, though? Let's simplify it with a metaphor: we need a cat, some cheese, and a few hidey holes of safety in between to rest at while we run from the cat and chase that cheddar. If we stop, the cat catches us and we never get the cheese, so we have to keep going. What pulls you? What pushes you? Who, or what is distracting you, and how do you narrow your focus and reach milestones in pursuit of your goals? For me, what pulls me is the feeling that I have unrealized potential, that I'm somehow falling short of what I should be capable of - and I'm eager to bridge the gap. What pushes me is the thought of watching my daughter grow up from the sidelines. I've missed milestones and checkups already. How long until I miss first days and game days and father-daughter days? What focused me is the quote at the top of the post. It opened my eyes to the cost of my ignorance, showing me that not knowing how to make ten grand was costing me seven every month. If there's one more thing I'd add, it's that you should try to lower your action threshold and flatten your extinguish curve - make convincing yourself to try something easy, and make giving up too early difficult.
Tip #2 - Execute - Just Win
It takes 20 hours to learn most things, but most people spend 20 years delaying the first hour. Don't be that person.
Should you start a pressure washing business? A laundromat? A bookkeeping business? A tutoring or test prep business? Maybe hit up a marketing guru or a successful cousin and try to land an internship at their firm to learn higher value skills? Paralysis by analysis keeps you from saying yes, but once you can agree to trying things, the next problem is saying yes too often - and we need laser focus. Impulse control, remember? Everything is an opportunity, but none of them will work unless you pick just one. When you start, chances are you'll be responsible for everything. Marketing, finances, fulfilment, labor, and all the other hats, too. If you want to do anything well, you're going to need to limit the number of things you do.
When you start saying yes, then learn to say no, you'll most likely find yourself in what I call the lonely chapter. It's a season of no. Places you used to go will have an empty seat, friends you used to hang out with will be sidelined, and sometimes your circle will shrink. Don't hold it against them. People say, "you've changed" because they don't know how to say, "you've grown." You'll be too different to fit in where you used to, but not different enough to be invited into newer, more appropriate surroundings. Just have hope, and remember this:
Extraordinary results come from doing ordinary things for inordinate amounts of time.
Tip #3 - The 5 Stages of Entrepreneurship: Failing Forward
Uninformed Optimism
Informed Pessimism
Valley of Despair
Informed Optimism
Achievement of Goal
You get an idea, and you get really excited about how you're going to make all this money, help all these people, do all this stuff. You find out really quickly that your latest bright idea is going to be a lot harder than you thought to pull off. Then you find out it's even harder than that. Most people derail here, jumping off the track and going right back to the top with a new idea, over and over. Stick with something long enough and you'll see the light at the end of the tunnel. You'll see the obstacles and the path around them, too. The first few ideas you entertain may not pan out. That's okay. The goal is to learn, to grow, and to fail forward. I fell into the valley of despair when my first idea turned out to need an audience, which I didn't yet have, and my second idea needed me to commit to 100's of cold calls per week (and I slept during business hours). My latest and greatest idea, which led me to build this site, has me somewhere between 3 and 4. Here's hoping. The general idea is to execute on your best bad ideas as soon as possible because it's where you learn. Your first idea or two or ten probably won't amount to much, and that's fine. Expect failure - just be directionally correct. Go in a general direction you think is right, and course correct along the way until you exhaust all your best bad ideas, leaving you with only good ones to try next.
Success is the ability to go from failure to failure without a loss of enthusiasm.
Tip #4 - Reverse Engineer Success with Inverted Thinking
We're wired to identify threats in the environment. See, we pick up on negatives quickly, while positives are harder to see. It's great for survival but think about the last time you felt taken for granted or overlooked, and then consider the last time you made sure someone else knew they weren't. After you send a suddenly very important text message relaying your appreciation for someone, go ahead and make use of this threat-detection engine by writing out how you could guarantee failure in executing one of your ideas - how could you make sure all your effort is wasted; all you build destroyed? Don't concern yourself with customer service, don't bother asking for feedback to improve your service, don't answer the phone when it rings, don't show up on time or conduct yourself in a professional manner, don't vet your employees, etc. It's easy to build a huge list of things that guarantee you fail. Now invert everything on the list. Customer service becomes paramount, getting feedback and testimonials, ensuring prompt communication and punctuality, professionalism in a qualified, experienced team all become a priority. This trick is really handy when you're stuck or lost.
Tip #5 - Repetition Negates Luck
In the martial arts world, we say "train hard, test easy." There are some people out there who won at life - they got lucky and found success by a fluke, and stripped of it, could never reproduce that success because they never learned how. Another saying we have is, "don't practice until you get it right; practice until you can't get it wrong." When you've found something you think is worthwhile, do it over and over again and get really good at it. Skills compound, and investing heavily in the S&ME500 can yield higher returns than any index fund. You could put $5k into the S&P and get a 10% return at the end of the year (if you're lucky), or you could spend that $5k on a course to learn a new skill that increases your annual income by $10k or more, indefinitely. Which seems like the better investment to you?
If I'd found myself moving forward with one of the ideas I rejected, I would've cold-called several hundred businesses every week in hopes of getting 10 or so clients. I'd have written down every new objection, every new obstacle, every type of resistance surrounding my offers, everything that seemed to go well in my phrasing and tonality, and crafted a script outline that would enable me to come to every conversation very prepared. At some point the next call would've been my thousandth and a prospect's first. The confidence and ease with which I could have that conversation far exceeds that with which I'd have had my first. Though I may have gotten lucky on that first call and gotten a client signed, having had the thousand calls for practice would ensure I could get lucky an awful lot.
Tip #6 Poor Customers Are Too Expensive
Poor people don't have enough money to make you any, unless you can sell to a LOT of them all at once (FYI for the first 1M people who buy, my eBook on how to make a million dollars a year is only $1!)
It's a good idea to sell to people who have money. One good framework to help you with this is the CAOS principle. It stands for Concept, Audience, Offer, Sales. How it works:
Find a problem you want to solve, decide how to solve it at a sufficiently high level and do back of napkin math to figure out how many people you could serve, and at what price point, to reach $10k/mo in revenue (this means the money you charge, minus what it costs to make that money).
Find an audience who can and would prefer spending their money rather than their time (aka rich people) to solve the problem. It's a lot easier to sell hotdogs outside a movie theater than outside a restaurant. Find a starving crowd.
Define an avatar and tailor your offer to them, providing enough value that you can charge $1,000 or more.
Structure this business around making the sale - and pay others for the work. You want to be the organizing force, not the labor. Chances are, you're going to be the labor too, at first. Hire when your time, once freed, makes you more money than an employee costs.
Tip #7 Everything is Downstream of Lead Generation
Having a great product or a great service is useless if there's nobody who knows about it. Advertising is the purchase of eyeballs - you pay for attention to make known what it is you do for money. A lead is a person you can contact. An engaged lead is someone you can contact who has shown interest in your stuff. A qualified lead is someone you can contact who your product or service is meant for. Generating engaged, qualified leads is something I quickly identified as a crucial obstacle to overcome, so I set out to learn how. I discovered a software I liked, learned how to use it, and wouldn't you know it? The skills I've obtained from dabbling around, failing at other things led me to discover a problem, learn to solve it, become an affiliate, craft some offers and create this website with a clear path forward from Affiliate to Freelancer, to Agency Partner.
Conclusion
I didn't know how to make this website until I failed no less than four times to make other ones I was happy with. It's still not finished. I didn't know how to write a blog post until I scrapped three other drafts of this one. I'm still not sure it's up to snuff. Maybe you want to be an entrepreneur, maybe you want to enjoy the safety of employment at a higher pay rate, or maybe you're already a business owner evaluating whether to do business with me. Maybe you're just here with popcorn, waiting on me to either crash and burn or take off like a rocket. At the time of this writing, I'm nobody - just some guy, a failure, even. But just wait. Stick around, and I just might fail all the way to freedom. Stick around and I just might drag you to the top with me.
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