The Loser’s Guide to Winning At Life

A trip to Las Vegas taught me how to succeed without really trying

Las Vegas, NV, USA // Photo: John Gorman

I went to Las Vegas over the weekend in what was my first honest-to-goodness vacation since October 2019. I don’t typically love Vegas — I don’t club, gamble, or enjoy touristy things or bro-y meatheads — but there are few better cities in the U.S. for food, sunshine, and feeling like you’re “off the clock.”

You say you’re going to Chicago and work will send you texts and emails. You say you’re going to Seattle and work will assume you’re there for a job interview. You say you’re going to Vegas and your bosses leave you alone because they assume you’re drunk by 9 in the morning.

“Off the clock” was all I wanted. I didn’t even bring my laptop(s). The vacay was great — damn near perfect, actually.

I’ve realized there are two species of people who go to Vegas:

  1. Those who can’t afford to travel, hardly ever, and so they splurge on Vegas for their quadrennial checkout from the grind.
  2. Those who are rich as fuck and just want to fuck off for a long weekend.

You can tell the difference between the two types almost instantly: The former is window shopping on the casino floors and hitting up the buffets in oversized T-shirts, while the latter is in oversized sun hats at the Vdara deep house pool party.

Strangely, neither group seems to be having all that good of a time. They’re too day-drunk (and in that heat, that isn’t a tough level to clear), too hung up on where they’re off to next, or too immersed in the way they look through the lenses of their phones to taste their food. One group’s obsessively trying not to blow money, the other can’t seem to blow enough to satisfy their most decadent desires.

Me, I like to think I struck it straight down the middle: extraordinary meals at highly recommended restaurants off the beaten path, a solid block of time at Meow Wolf, a drink at the Chandelier in the Cosmopolitan, the requisite photos in front of the Bellagio fountains. Aside from the rampant 20+ minute wait times for rideshares, I was never really in a rush anywhere, and I largely avoided cliche — I hit the right notes and let the silence in between them become the music.

Of course, you didn’t come here for a travelogue, and I didn’t come here to give you one, but here comes the tie-in you most definitely crave: I didn’t have to try all that hard to enjoy myself. (There’s also a litany of reasons why I could chalk up all that lack of effort to varying layers of privilege; there are also plenty of people like me who go to Vegas and have a miserable time.)

I didn’t have any expectations; I knew where I wanted to stay; I had impeccable company; I had a few ins at key places; I knew where we wanted to go; I budgeted for all of it; I didn’t overpack the schedule nor do the things I didn’t care for just because “they’re there” and “you just have to.”

Success in life, succinctly, boils down to that:

  • Reasonable expectations
  • Comfortable accommodations
  • Good people with you
  • Good people willing to help you
  • A clear, yet flexible, plan of attack
  • Enough money to get by
  • Time well spent

If you can manage all that, then you’re doing just fine. You don’t need to shoot for the moon, or outlive your means, or pack it all in, or be swayed by the masses. You can just be. And if you can just “be,” then you’ve won. Here are the three steps to success:

Step 1: Relinquish control

The future’s rarely going to cooperate with you. I don’t care how many vision boards you make, or how many affirmations you say to yourself, or how hard you work for what you want. Outside events will interfere with your best-laid plans, your mind will change, people will tell you no, your efforts will be in vain. A future is a “probability,” and many of them could come to pass.

There’s a tendency to throw up the blinders when gunning for a goal, to envision the ideal and nothing else. However, kicking the cans of happiness and success down the road places them as uncharted destinations. You’ve taken things that could be tangible and made them intangible. Why would you do that? Why put off your own happiness and success instead of spending your time in ways that make you feel happy and successful in the now?

We often hear people say, “Would you endure six months, a year, five years (or whatever) of hell to reach a lifetime of heaven?” And most people say yes. Me, I’d ask, “Why willingly subject yourself to that much hell? Life will do that for you on its own.”

For me — and, given that this is already the title of a well-known book, I’m sure I didn’t come up with this — it’s all about power versus force. Force is any time you try to do something, while power is when you let it happen. There’s almost nothing I’ve done in my life to contribute to my happiness and success that didn’t feel nearly effortless. Those things came to me often when I wasn’t trying or looking for them.

By far, the tougher ask was — and remains —learning not to react to things that detract from my happiness and success. Some folks call this “radical acceptance.” By merely accepting adversity, failure, rejection, hardship, tragedy, unfairness as inevitabilities to navigate rather than mistakes to avoid, it’s easier to work with life as it is rather than what you force it to be.

There’s that word again: force. Sail in the direction the winds blow you; getting blown off course doesn’t mean your ship’s broken or your compass needs recalibration. It means the weather didn’t cooperate. Good luck blaming yourself for that.

Step 2: Discipline yourself

Now that you’ve recentered your focus on the here and now, here’s the bad news: Your time, attention, energy, and capital will be limited.

You can’t eat all the food, you can’t drink all the drink, you can’t make every meeting, you can’t know everyone, you don’t have the bank account of a Musk or Bezos, and should you find yourself in possession of a haul that large, or aspire to it, that means you’re likely a sociopath: you don’t extract that much wealth from a global economy that leaves billions struggling to survive or put that many past, present, and future competitors out of business, without being a sociopath.

But if you can accept that you can’t do it all, and won’t do it all, prioritization becomes clearer. Given the inarguable scarcity of your life, how will you spend what precious little you have? So many conflate discipline with a tireless work ethic. But discipline more accurately means rest, care, and focus.

Life’s a vacation in the sense of you’re here for a limited time, with limited money, and limited energy. So what will you do with it? How can you make the most of it without burning yourself out? How can you spend wisely? (And you must spend to derive pleasure, whether that’s in a monetary sense or otherwise.)

Leave yourself time, energy, attention, and capital left over. Don’t overbook. Don’t overwork. Don’t overspend. Don’t overcommit. Don’t overextend. Pushing your limits isn’t a sustainable lifestyle. Grinding’s for suckers. Leave your laptop at home. Leave space to be surprised.

Step 3: Assemble your team

Every time I see people spout aphorisms like, “it’s lonely at the top,” or “I’m a self-made man,” I roll my eyes. No, it isn’t, and no, you’re not. It’s lonely if you don’t endear yourself to anyone, and if you lone wolf’d the whole journey then you probably didn’t get much of anywhere.

Whole communities of people will rally behind you, work with you, lift you, or help you along if you allow them and — and this is key here — make them feel good when they do. People like to help people that they like and believe in. People will help when they feel it’s in their best interest to do so, or when they receive some kind of reward in return: happiness, reciprocation, security, love, community, peace, knowledge. You want people to help you? Offer those things.

People won’t buy from you unless they also want to be like you. We buy from people we want to be, or people we want to hang out with, or people we don’t think we’re capable of becoming but wished we could. We buy from people who take an interest in us just as much as they are interesting to us. Work on being that person, first.

Then just ask. People will help you if they know what you’re doing and what you want to do and what’s next for you. If you’re someone they respect or adore enough, sometimes they won’t even wait for you to ask them. (In many cases, that’s an example of privilege; in other cases, that’s an example of charity. Learn to spot the difference.)

As an anecdote, we went to a bar — Atomic Liquors — at the recommendation of a close friend and seasoned Vegas vet, and had delicious cocktails. We struck up a pleasant conversation with the bartender. She asked us what we were going to do next. Then she suggested a place I wanted to try, but couldn’t get a table. “Let me make a phone call,” she said, and talked to her friend who tended the bar there that day. Now we had a table and a delicious meal, to boot.

I didn’t win any money in Vegas. (Sure, it was because I didn’t bet any.) But I still felt like a winner. There was a “now,” and I enjoyed it. I succeeded in planning and executing the plan. I didn’t control too much. I didn’t try to do too much. I had great company and a good group of people advocating on my behalf.

I budgeted for the trip and spent extravagantly, but still have enough leftover. My bills are already paid. I am content. If I can enjoy the now, for long enough, I’ve enjoyed forever, minus the adversities life throws at me without my consent. I imagine I’ll overcome those, too, or I won’t.

That’s the power. The power of disciplined surrender to the ever-shifting current of life — a neverending and largely inevitable stream of setbacks and successes. When you’re able to accept this, you realign your energy into the state that it needs to be: a state of presence. Only when you are present will you be able to truly reach any goal you set for yourself. If you accept what is, and who you are, as good, but limited in your capacity to control what comes, then you’ve achieved that state.

Fact is: Most of us are living our best lives, or close to it, most of the time, relative to what the cosmos and our baked-in limitations permit for us. That “you could be so much better right now” messaging is the domain of internalized capitalism, influencers (the ultimate internalized capitalism), life coaches, and people trying to sell you e-courses or degrees from for-profit universities.

Sure, our waves may crest and trough. Oftentimes we’ll feel like losers. But if our trend line slopes up overall, we’re winning, and we should celebrate that. We don’t have to force it. We just have to allow it.

Essayist and storyteller on life, liberty and the battle for happiness. Several million served. Words at Human Parts, Forge and PS I Love You. IG: heygorman

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