undefined - How To Make The Most Out of Your 20s

How To Make The Most Out of Your 20s

How should you navigate your 20s - the most important decade in your life? For many people, it's an age with fewer responsibilities: no kids, no mortgage, no restrictions. And so it's actually the best possible time to go hardcore: to take risks, invest in yourself, and surround yourself with like-minded people.

December 4, 202421:15

Table of Contents

Segment 1

📝 Intro

Dalton and Michael introduce their podcast episode about how to spend your 20s, positioning themselves as "Elder Millennials" with perspective on this important decade. They note that while they're no longer in their 20s, they've observed many young people become successful through Y Combinator and believe there are valuable lessons that apply even to those who don't want to start companies.

"This is Dalton plus Michael and today we're going to talk about how to spend your 20s... as people who are no longer in their 20s."

They position the episode as sharing wisdom about navigating this critical decade effectively, whether you're a founder or not.

🏃‍♂️ The Hedonic Treadmill

The hosts explain the concept of the "hedonic treadmill" - the psychological phenomenon where people quickly adapt to new pleasures or rewards, causing satisfaction to fade. They describe how it works:

"It's this thing where no matter what's going on in your life you will get used to it. When you get a new cool thing when you're a kid and you get a new toy you're like 'wow this toy is awesome what a great Christmas I'll never want for anything again' and then two days later you're like 'oh yeah this toy sucks, I want more new stuff.'"

They highlight how Instagram has amplified this problem by showing the "0.1% of people's lives that are awesome," creating unrealistic expectations that drive dissatisfaction. This creates a dangerous cycle where people constantly chase the next thing, never feeling satisfied.

"Everyone's sharing videos and photos of them living their absolute best life... it's fake. They're clipping the 0.1% of their lives that are awesome and putting it on a site and you're like 'wow everyone is living a more awesome life than me, every day, all the time, my life sucks.'"

They note the issue isn't limited to social media - even those who "grow up super rich" face this problem of having "already done all the fun stuff" with "a lot more life to live."

🐢 Don't Speed Run Life

The hosts propose a strategic approach to hack the hedonic treadmill by "intentionally delaying each step" in life's progression. This creates room for future growth and continuous improvement rather than exhausting all options early:

"The hack is to intentionally delay each step and to give yourself room and upside, so there's always more steps for you to climb in the future versus speed running it and getting it all at once."

They provide practical examples:

  • Your first post-college apartment "should not be much nicer than your dorm room" even if you can afford it
  • Your first vacations "should probably not be that nice"
  • Your first car "should probably not be that nice"

By resisting the urge to immediately upgrade your lifestyle when you have the means, you create a sustainable path of growth and appreciation. This approach helps remove "hedonic distractions" so you can focus on more important things in your 20s.

💪 Go Hardcore Early

The hosts advocate for pursuing the most challenging path early in your career when you have fewer responsibilities:

"Do the most hardcore thing early in your career because you can always mellow out, you can always pull the rip cord and do less hard things. It's very hard to go the other way around."

They observe that despite this seeming obvious, many young people avoid intensely challenging paths, possibly due to messaging about burnout and work-life balance. They suggest this concern is misplaced - youth is precisely when you can and should push yourself harder.

The hosts use professional paths as examples:

  • Medical school: "If you choose to go to med school that is a hardcore thing and once you get your MD you could be a more mellow doctor"
  • Law school: Similarly front-loads the difficulty
  • Writing: "If you want to be a novelist you should be a really hardcore novelist in your 20s and write a lot"

They emphasize that regardless of career, "the more hardcore path just gives you more options when you're older" and helps you discover your true capacity for growth and achievement.

🎲 Take Risks When You Can

The hosts emphasize that your 20s present a unique opportunity to be risk-seeking instead of risk-averse:

"It's hard to contextualize how much of your life you'll spend being risk averse... you have kids, you have a mortgage, you have elderly parents, you yourself are elderly, you are less willing to take risk."

They observe that despite this opportunity, many young people avoid risk, often due to parental advice or fear. They challenge the notion that traditional employment offers security, noting that the idea that "you get a job and you can do that job at that company for the rest of your life is already been disproven."

The hosts offer practical advice for evaluating risks:

"What's the worst that can happen? Be explicit... if that happens, then what can you do? Could you go get a job?... Talk through explicitly what the worst thing that could happen if you take a risk is and it might not sound as bad as you think once you name it."

While acknowledging that risk-seeking isn't appropriate for everyone's circumstances, they suggest many people have more capacity for risk than they realize: "There are a lot of people who their starting conditions would allow them to be risk-seeking but they don't realize it."

👪 Define Your Own Path

The hosts discuss the challenge of separating your own aspirations from parental expectations during your 20s:

"Your 20s is really the first moments where your plan's kind of your own. If you're following your parents' plan you chose that... when you're 23 and you're following your [parents' plan]... are you living your own life or for the expectations of you?"

They acknowledge the difficulty parents face in not having visions and expectations for their children, but emphasize the importance of questioning and owning your path. They note that many people reach their 30s and realize they never truly evaluated whether they wanted the path they've been on:

"I think there are a lot of people who kind of look back and they're like 'oh I didn't question my plan enough in my 20s'... I woke up in my 30s and was like 'wait, did I really like the path that I walked? Did I ever spend a lot of time thinking about what do I want?' and then they realize in their 30s like that's a little... some of that's baked."

The transcript segment ends with the hosts beginning to discuss the importance of peers and who you spend time with, noting that "your personality is just an amalgam of whatever the six or [seven people you spend most time with]" (cut off).

👥 Choose Your Circle Wisely

The hosts emphasize how profoundly our peer groups shape our identity and worldview:

"Your personality is just an amalgam of whatever the six or seven people you spend the most time with... a lot of the things that we think are our own ideas or our own identity is not, it's just you soaked it up from your peer group."

They note the surprising influence of random factors like college roommate assignments:

"It's funny to think about how much of our lives are dictated by who we get randomly assigned as roommates in college... is there any bigger decision in what kind of person you grow up to be?"

However, they argue this is "hackable" like the hedonic treadmill - you can intentionally choose who you spend time with based on who you want to become:

"If you want to change, if you want to do a startup, having more friends that are startup people that won't be like 'startups are dumb, startups are risky, why would you want to do that?'"

They explain how social groups normalize behaviors and beliefs:

"Everyone becomes a centrist in whoever they're surrounded by, and so if you're surrounded by extremists on any topic, you'll think you're a centrist but you're actually an extremist."

They recommend being willing to make significant life changes to shift your social circle:

"A hack to changing your life is changing those people... and changing those people might require changing where you work, changing where you live, moving to a different city."

The hosts note that your 20s offer unique flexibility to make these changes since "they usually only impact yourself," and reassure that "your really good friendships will survive" even with distance and time.

❤️ Seek Long-Term Relationships

One host offers what he describes as "controversial advice" by advocating for serious relationships in your 20s:

"I think you should seek long-term relationships in your 20s. I think a lot of people would say 'oh you don't want to get tied down with a partner'... I'm not saying like get married, buy houses, have kids."

He argues that having a supportive partner is particularly valuable during the intense work periods they've been advocating for:

"There is something really powerful about having a strong partner especially when you're trying to do hardcore things and you're trying to work really hard... having a really good partner actually unlocks some of the gears."

He suggests that being in stable relationships is a valuable skill to develop:

"Being in the practice of being in stable relationships is good. It is a good hobby to develop that your future self will enjoy."

Conversely, he cautions that the opposite pattern can create problems:

"The person who never wants stable relationships, that just wants to be on Tinder, that doesn't ever want to be tied down... is trying to do FOMO every minute. You're kind of training your body the wrong lessons."

He frames relationship choices in terms of investment versus debt:

"If you do aspire to have a family one day, you can start orienting yourself in that direction in your 20s, or you can create debt for yourself... I'd argue the debt thing is harder."

🌍 Beyond Startups

The hosts address potential criticism that their advice is only relevant to startup founders:

"Most people don't want to start a startup. Why is any of this relevant to me as a person that doesn't want to do a startup that's watching this video?"

They respond by emphasizing the broader applicability of their principles:

"We're not trying to presuppose what you want to do with your life. I think we're kind of trying to say hey, if you have something tricky you want to accomplish, here are some tricks that can help you."

They highlight the commonality between startup founder experiences and "the experience of someone who wants to do anything that's really hard."

The hosts acknowledge a difficult truth that many don't want to hear:

"Investments in your 20s pay off for the rest of your life... whether they're good or bad investments."

They recognize the emotional difficulty of this reality:

"Anyone who lived through a childhood where you're kind of told 'hey every door is open to you, it's a world of opportunities' hates being told 'hey, this decade, doors start closing'... that does not feel good, but it's truth."

🧱 Working Within Constraints

The hosts address objections from those with significant life limitations:

"What if I have debt or I have to support people? You guys are giving all this advice, this is just not applicable to me, this is not applicable to most people."

They acknowledge the reality of specific limitations:

"There are a lot of people out there that have extremely specific limitations... some people are stuck in a country and they can't get out."

Rather than insisting everyone should start companies, they reframe their message:

"This is not 'go do a startup, startups are for everyone.' That's not what we're trying to say. What we're trying to say is that doing maximum effort is probably the only way you get yourself out of a not great situation."

They emphasize the power of perspective and agency:

"The people who have the most challenges, when they can be optimistic and when they can see themselves as agents as opposed to kind of victims, crazy can happen in their lives... by just switching what's in their head."

They encourage applying whatever lessons are relevant to individual circumstances:

"You might not be able to apply to YC, you might not be able to move... but there's probably something in your life that you can apply one of these lessons to that is a chance of making things a little bit better."

🎓 Beyond Elite Education

The hosts address concerns from those without prestigious educational backgrounds:

"What if I didn't go to a good school? I feel as though the people who went to a good school, they still have a lot of doors open. I'm getting out in the working place and I don't see the doors."

They suggest identifying organizations doing interesting work in your field of interest:

"Try to identify what companies or workplaces have the most interesting people doing the work you're most interested in... I would try to get any job there."

The hosts explain why this approach works:

"Once you're in the room, once you get into an organization, you will get to meet and be around all these other people and soak up the culture."

They note that Silicon Valley has many successful people who didn't attend elite schools but "just got in the door somewhere with any kind of random job," and once inside, "their intellect and their skills and their abilities allowed them to win people over."

They clarify this isn't about seeking prestigious brands for your resume, but rather about surrounding yourself with talented people - who are often found in early-stage ventures: ::QUOTE_START::Many times super talented people are at the beginning of stuff, where getting in is easier.::QUOTE_END::

🚪 Getting in the Game

The hosts share a personal anecdote about an intern at one of their startups:

"We had an intern at my startup that went on to get into YC, start a company that's generating tens of millions of dollars in revenue, and did not go to good school."

Before joining their company, this person "was working as a security guard for a housing development." When asked about his qualifications for a content moderator role, he explained his experience managing chaotic situations at a college housing community gate during nights and weekends.

The hosts use this example to illustrate how "getting in the game" can be straightforward: ::QUOTE_START::Getting in the game is as simple as... once he got into your startup, then he was hanging out with you guys, like all the founders... you're in the game.::QUOTE_END::

They highlight how early-stage startups offer unique opportunities: ::QUOTE_START::This is what's so cool about startups... small startups... humans are reading every email... your email got read, and when people are in those startups and they're desperate, they're open to giving people opportunities.::QUOTE_END::

🔄 Final Advice

The hosts conclude with their key takeaway:

"Don't be the 30-year-old who wakes up and says 'what happened to my 20s?'"

They offer a sobering reminder:

"This is one of those things... hard life truths... life does move, years don't come back."

Their final observation reinforces the importance of using your 20s strategically:

"Most of the most successful people we know, they were laying that foundation in their 20s."