101 Secrets for Your Twenties

1. Let Go of "Supposed To" and Embrace the Messy Reality.

Let go of “supposed to.” Tie an anvil around its neck and throw it out to sea.

Unmet expectations. Many enter their twenties expecting a box office smash, a life that feels like it's "supposed to" be perfect, successful, and figured out. This fairy tale blueprint, often based on external pressures or idealized visions, is a lie that steals peace and productivity, leading to frustration and the feeling that something is wrong with you. The reality is often messy, mundane, and far from the imagined successfest.

Death by expectations. Trying to live a life based on someone else's blueprint or an unrealistic timeline leads to Obsessive Comparison Disorder and constant discontent. No one has it all figured out right after graduation; not everyone walks into their dream job or gets married on a predetermined schedule. Your current moment, however imperfect it feels, is exactly where you need to be for your unique journey.

Embrace your path. Stop trying to live other people's lives or chase a fictional "supposed to." Your story doesn't fit into theirs, and cramming it in is like mixing genres in a movie – it just doesn't work. Instead of being frustrated by unmet expectations, accept where you are, knowing that clarity and purpose often reveal themselves over time, not instantly.

2. Your Twenties are a "First Draft" - Expect Struggle and Failure.

We have to be willing to allow ourselves to write some terrible first drafts.

Embrace the process. Just like a writer produces many atrocious first drafts before finding the right story, your twenties are a period of getting words down on paper that you'll edit later. Plans will fail, jobs won't be glamorous, and you'll experience ample amounts of un-success. This Frightful First Draftdom is a necessary part of the process, not a sign of failure.

Struggle builds story. You can't have a good story without a good struggle. Your twenties are a decade exploding with intensity and ambiguity, anxiety and excitement, purpose and pointlessness. This turbulent season, where life might feel like it's dismantling you, is actually the most important period of development, teaching you how to fail, struggle, and persevere.

Failure is fuel. Don't let failure be a death sentence; see it as just one more sentence before you turn the page. Failing means you're finding a more profound way to be successful, if you're willing to learn from it and have the courage to try again. It's part of lifting a weight heavier than you, tearing muscles so they can become stronger.

3. Meaningful Relationships Require Intentionality.

Making and keeping friends in our 20s takes intentionality.

The Friend Abyss. Making friends was easy as a kid or in college with shared experiences like classes, dorms, and activities. But post-college, you enter the "Friend Abyss" where old friendships fade due to distance, marriage, kids, or demanding jobs. Keeping up becomes harder than G.I. Joe's abs, often reduced to voicemail tag or annual Facebook birthday posts.

Making new connections. Finding new friends, especially couple friends, post-college is even harder. Between work, family, and basic needs like sleep, who has time for the long, awkward process of "Friending"? Yet, we are the most uber-connected, plugged-in generation, also the most Insanely Isolated. This lie that we're alone in our struggle magnifies anxiety and depression.

Prioritize connection. To combat isolation, you must be intentional. Ask yourself if friends are truly a priority in your busy life. Get involved in activities you find appealing – sports teams, community service, support groups, or church – places where shared experiences can foster new connections. Most importantly, pick up the phone when a friend calls; slay the ME-MONSTER of your schedule and time.

4. Navigate the Job Jungle: Learn, Grow, and Build Your Brand.

Your Own Website is what a resume and power suit were in the ’90s.

Diploma is just a pinky toe. Your college diploma isn't a passport to success; it's merely a pinky toe in the door, giving you one minute to prove yourself. Many twentysomethings face the humbling reality of unemployment or sludgy jobs that feel monotonous and meaningless, far from the dream job envisioned on graduation day.

Learn from the crud. Even dung-filled jobs offer valuable lessons. Working at a call center taught consistency and patience. If you're stuck in a job you dislike, figure out what you need to learn there – whether it's showing up daily, dealing with difficult people, or mastering a skill – and learn it. If you don't, you might find yourself in a string of lousy jobs later in life.

Build your brand. Don't passively wait to be discovered. In a competitive market where a bachelor's degree is the new high school diploma, you need to articulate and present what makes you unique. Creating your own website is the biggest amplifier of your job search and brand-building efforts, allowing employers to see, taste, and touch your skills and potential in a visible, accessible way.

5. Face Your Insecurities and Seek Help.

We must actively face these insecurities and work on removing the root, or the weeds will just keep growing back.

Insecurity's grip. Insecurities, often stemming from past experiences like acne, bullying, or difficult family dynamics, can become permanent fixtures, affecting your present like a sci-fi movie monster trying to pull you into the mud. They don't disappear with age; they become more pronounced and ingrained if not addressed. Many grow into the person they were always afraid of becoming, their identity mashed together with their insecurities.

The struggle for help. Finding help for issues like depression or anxiety can feel daunting and isolating. It's not something easily posted on social media, and finding an affordable counselor you connect with can feel like a miracle. Yet, everyone needs help; sometimes the greatest help needed is help finding help.

Attack the swamp things. You need support to face these "Swamp Things" in the eye. Seek help from trusted guides – a friend, parent, mentor, counselor, or pastor. Find support to remove the root of your insecurities, telling them they have no power over you. This inner work, though rocky and scary, is crucial for growth and becoming the right person for healthy relationships.

6. Comparison and Validation are Toxic - Focus on Your Own Path.

Don’t cram YOUR PLOTLINE into someone else’s story.

The comparison trap. Nothing is more vital to twentysomething un-success than constantly comparing yourself to everyone else – friends, celebrities, coworkers. Social media makes this easier than ever, allowing you to pore over others' seemingly perfect lives, measuring their smiles, house size, and job titles, fueling Obsessive Comparison Disorder (OCD). This habit from hades drives depression, anxiety, and discontent.

Validation addiction. Many are addicted to external validation – likes, retweets, affirmation from the masses. This need is often groomed from a lifetime of seeking approval through grades, awards, and praise. Social media simply amplifies this addiction, making your highs and lows dependent on how many people affirm you online, turning Google Analytics into your drug.

Put on blinders. To cure OCD and validation addiction, put on blinders and become Forward-Focused on your own path. Cut back on internet and TV use, which turn your comparison problem into a Hummer guzzling energy. Celebrate what you do, big or small, instead of obsessing about what you don't have. Sail your own ship instead of drowning trying to swim to everyone else's.

7. Create, Don't Just Complain.

The more you create, the less you complain.

Complaining as currency. Complaining, often laced with cynicism, has become a national pastime and social currency, especially for a generation that entered a tough economy. It's easy to lament injustices, slow Wi-Fi, or bad bosses, feeling justified in singing woes from fields ravaged by locusts. But complaining is passive and powerless, like a rash that's easy to catch and tough to get rid of.

The power of creation. In contrast, creating is proactive and powerful. Instead of standing by the problem pointing out what's wrong, create a solution. Instead of ingraining discontent, work towards a new way forward. Create a movement, a relationship, a tool, a conversation – big or small, just do something.

Choose to build. People gravitate towards Passionate Pursuers, running from Complacent Complainers. Opportunity isn't just something that floats by; it's something you create. Replace moments where you have every "right" to complain with moments of creation. Pick up the torch of the Creator and make beautiful things out of the dust in a broken world.

8. Embrace Being Lost; It's Part of Finding Yourself.

Being lost might be the exact spot that I can be found.

The Quarter-Life Crisis. Feeling lost, stuck between being adult and child, wondering when you'll feel like yourself again – these are signs of a Quarter-Life Crisis. It's a period of intense transition where everything familiar becomes unfamiliar, like being spun around in a corn maze in the dark. This crisis is not a failure, but a necessary stage of exploration.

Exploring the unknown. Growing up was linear – school, college, job. A Quarter-Life Crisis is when you stop climbing the predetermined stairs and start exploring the unknown rooms on the 15th floor. It's terrifying because there's no map, no syllabus, no professor with answers, just you and endless possibilities, some smelling like mothballs and old pee.

Purpose in the lostness. Explorers get lost on purpose, with purpose. They lose sight of the familiar to find something greater. Being lost forces you to learn how to fail, struggle, and persevere, teaching you how to really see in the dark. Don't go on this journey alone; call in help, a support party. Being lost is the exact spot where you can make your biggest discoveries and find the right place to build your home.

9. Define Your Own Success, Not Someone Else's.

If you don’t define success, it will stay an unidentified flying object that you’ll never take a picture of.

Subjective success. Success is the most subjective word there is. If you don't paint a picture of what it looks like for you, you'll end up chasing a figment of someone else's imagination. You can't find something you haven't defined, and letting others define it for you means you'll always be chasing an unidentified flying object.

Beyond the metrics. Society often defines success by external metrics: salary, job title, house size, relationship status. While these might be components, true success is personal. It's about aligning your passion with purpose, making an impact, finding fulfillment, and living a life that is authentically yours, not just virtually appealing to others.

Your personal records. Stop living for "them" and their perceived level of awesome. Focus on achieving your own Personal Records, not just posting your own PR (Public Relations). Define what success means in terms of growth, learning, relationships, and contribution, not just accumulation or status. This allows you to pursue what truly matters to you, regardless of external validation or comparison.

10. Marriage is Partnership, Not a Problem Fixer or Fairy Tale.

marriage doesn’t fix any of your problems. No, marriage actually puts a magnifying glass on how many problems you really have.

Beyond the fairy tale. Many dream of marriage as an end to loneliness, insecurity, or personal struggles, expecting a Tinkerbelle who will sprinkle pixie dust and make life problem-free. This fairy tale expectation is quickly shattered; marriage doesn't solve your problems, it highlights them, especially when you bring a luggage set full of baggage into a small shared space.

The Four Pillars. Instead of searching for a mythical "The One," focus on finding "The Four" – someone who embodies four key partnership roles. This person should be your Best Friend (enjoying mundane moments together), Lover (attraction beyond just looks), Business Partner (navigating finances and goals together), and Wartime Ally (fighting for each other when life gets tough).

Creating your marriage. Marriage is built on a million mundane moments, not just magical ones. It's a business that requires open communication about finances and plans. Most importantly, it's a partnership where you face life's battles together, not against each other. You don't just have a marriage; you create it together, defining what it means for you, blemishes and all.

11. Don't Take Yourself Too Seriously; Be Ridiculous.

Never, ever, under any circumstances, worry if people think you’re ridiculous.

The trap of seriousness. Taking yourself too seriously is serious work, leading to a life in "Boredullameville" – efficient, predictable, and utterly un-awesome. It's where you prioritize policy, procedure, and looking important over genuine connection, creativity, or fun. This path makes as many waves as a dead leaf falling into a puddle.

Embrace the ridiculous. The #1 rule to living ridiculously is not caring if others think you are. Ridiculous people don't know or care about Boredullameville; they live with their bodies dipped in awesome, unconcerned with whether it's the "appropriate" use of resources. They are the weird, wild people who make you feel alive, lifting the heavy weight of Stuffy Adult-Dom.

Live with abandon. Ridiculous people believe in others more than they believe in themselves, constantly encouraging them. They care more about doing what's right than what looks right. They know facts aren't always factual and prioritize passion over perceived propriety. Choose to live ridiculously; it's a choice to live with abandon, joy, and a willingness to not conform to boring expectations.

12. Faith is a Personal Journey of Questioning and Saying Yes.

Faith is to stop pretending like you have all the answers altogether, or that you even know the right questions.

Beyond perfection. Faith is not about having all the right answers, presenting a problem-free life, or dressing up in Sunday best while pretending everything is perfect. It's not about impressing a judge to win a trophy. This pressure to appear problem-free, especially in religious settings, can make it hard to have honest conversations about doubts and struggles.

Wrestling with truth. Faith is a process of making it your own, often apart from childhood beliefs or parental influence. Sometimes this means staggering away to figure out what you're coming back to, questioning, wrestling, doubting, and feeling alone. This intense season, like being a piñata getting the candy slammed out, forces you to confront whether your life actually resembles what you say you believe.

Showing up as you are. Faith is about being stripped down to your bare essentials and simply saying, "here I am." It's about standing there as the judge tells you that you're cherished, blemishes and all. It's about hearing truth and saying yes, even when you don't have all the answers or even the right questions. God doesn't need you to be perfect; He just needs you to show up honestly.

Last updated: May 4, 2025