I Messed Up My 20s So You Don’t Have To: Important Life Lessons From a 30-Year-Old


So I have this Trello board of my life (see screenshot).

Trello board of author Lauren Holliday

Each stream or list (the vertical columns) represents a year of my life, and each “card” represents something important. Anytime I accomplish something, I add a card. Anytime something monumental happens in my life—good or bad—I document it in my Trello board. 

A year ago, I turned 30, which marked the end of my “defining decade” and therefore got its own little card in my yearly stream, because reviewing my twenties and loosely planning/setting goals for my thirties is important to me.

As I reflect back, I can’t help but feel a little disappointed. While this could be natural or a quarter-life crisis, I know I could’ve accomplished much more had I known what I know now—all of which I tended to learn the hard way.

Nobody really emphasizes how important your twenties are, and 90 percent of advice for twentysomethings is just plain bad—outdated, wrong, vague, or all of the above. So I decided to go through my Trello board, picking out the most important lessons for each stage of your twenties along with resources to help you not learn things the hard way. 

Think of it as the “Tools of Titans,” but on a much smaller scale and specifically for your twenties. 

In the words of Steve Jobs, you can’t connect the dots going forward, you can only connect them looking back. It’s true, hindsight is 20/20, but as you begin your twenties, I hope to give you the hindsight you need most now, so you won’t wake up at 30 one day and feel disappointed, which leads me to my first piece of advice. 


Know why 

If there’s one thing I wish someone would’ve told me well before age 20 it’s, “You don’t have to do what everyone else is doing.” 

This advice is practically common sense, so much so, it’s a freakin’ cliche… 

If everyone else jumped off a bridge, would you?

The above question is always used after someone does something someone deems wrong—usually an adult to a kid. But more kids should be asking adults this very same question. 


For example, we’re the most educated generation in American history, yet nearly half of all college grads are underemployed or unemployed. And while most kids think they’ll be making at least $60,000 straight out of school, the actual reality is more around $40,000.

Now, couple those findings with the fact that it’s ridiculously expensive to go to college, and it just increases every year. You’re looking at paying at least $20,000 each year, and that’s the low-end of the spectrum. 

If you’re like I was at 18, you have little to no idea what you want to do when you grow up someday. How would you? Nobody dreams of being a marketer when they’re a kid, but damn, I sure do love being a marketer today. Anyway, I digress. 

My point is: Did you even question your parents, guidance counselor, etc. about attending college? Do you even grasp the point of going to college? 

“To get a job, duh,” you might try me. 

And I’ll push back… “What job?” 

“I don’t know,” most of you will reply. 

And I’d ask: “So you’re going to spend $20,000+ / year to figure out what job you want?” 

Most parents have ~$18,000 saved for their kids to go to school, which is less than one year of schooling. This means most of you will be mortgaging your life away to pay $20,000+ year to study astronomy or American history (required prerequisites at many colleges). 

Looking back, it’s bat-shit crazy I did that. What the hell was I thinking, seriously?

I wasn’t. That’s the problem. I just followed the herd, and now, I have $67,000+ in student loan debt that just keeps accumulating interest and the only way to get rid of it is to die. I’m serious. You can’t file bankruptcy for student loan debt, which is criminal if you ask me, but that’s an entirely different post. 

My point of this spiel is to say, don’t sleepwalk your way through life. Remember to ask yourself why you’re spending so much energy on certain goals and activities.


For instance, are you becoming a lawyer because your dad’s a lawyer? Or are you studying law because you enjoy researching/reading, writing, and presenting/persuading? 




Don’t wait 


Once you know what you want and why you want it, make a plan to accomplish it. But don’t just assume you know what your plan should be without doing your due diligence first. 

This connects very closely with the above lesson, and it’s one of my biggest regrets thus far. 

Because I didn’t ask myself why I was going to college, I wasted a LOT of time just floating through life. I did exactly what the adults in my life told me—blindly following my peers to what felt safe and familiar—more classes and teachers who planned my entire year, one semester at a time. 

I thought I had to wait four years to get a good job. I thought I had to spend two years taking prerequisite classes, like astronomy and history, before I could declare my major and enroll in major-related courses. I thought I couldn’t do an internship until my third year of college. I thought I had to wait. 

Turns out, you don’t have to wait to do anything, except maybe becoming a doctor or lawyer. 

Seth Godin perfectly articulates this problem in his book “What to do when it’s your turn.”

‘One day, I’ll be ready’ 

That’s what she said to me. 

After four years of college, a year of interning, and an arduous six-month job search, she finally had her job as assistant to a talent agent. I asked her, ‘what’s the big goal, what are you after?’ 

Her eyes lit up. Apparently most people she ran into merely demanded a cup of coffee. 

‘My dream is to be an agent, to do what my boss does. I want to do what he does.’ 

Well, why not start now? Why not find clients now? Develop small projects, and find ways to get them in front of people who might want to produce them? Why wait? 

Because apparently you’re supposed to wait. 

You don’t take tenth-grade math until you’re in tenth grade. (Or at least wait until someone tells you to take advanced math, noteworthy merely because someone picked you to do it.) You don’t do the job until you’re offered the job. You don’t lead until you’re asked. 

The thing is, as the only good line in The Treasure of Sierra Madre says, ‘Badges, We don’t need no stinkin’ badges.’ 

There’s no permit required to be a talent agent. Or a leader. Or an impresario. There’s no authority who announces that it’s your turn to do much of anything. 

For most people, it never happens. Sometimes because they’re confused and honestly believe that they have to wait for the call. 

But mostly it doesn’t happen because they’re not thirsty enough. 

The catch is, it’s terrifying to not wait—to just do—and it can feel daunting, overwhelming, and dangerous. 

I’m certain the main reason I finally stopped waiting is because I was forced to. I was pushed off a cliff, and I wanted so badly to survive. 

By cliff, I mean my father cut me off, and I fell flat on my face. I had to drop out of college. I got evicted. And I moved back in with my dad at 23. 

It absolutely sucked, but I think it’s the main reason I actually succeeded in becoming financially independent. I was just SO hungry to gain control of my life, because I hated how my parents controlled it. 




Get money

Photo of Naomi Campbell with text

A wise person should have money in their head, but not in their heart.

— Jonathan Swift

College was a really stressful time financially for me—even when I was bankrolled by the bank of dad in my early twenties. I hated begging for money. Any time I wanted to buy something, I had to justify why I needed it. It didn’t help that nearly all of my close friends were extremely well-off and therefore had parents who gave them huge weekly allowances to survive. I just couldn’t keep up. 

It got so hard toward the end of my time in Orlando that I remember the time when I had to pay for McDonald’s in pennies. I seriously couldn’t even afford to put gas in my car to get to job interviews sometimes. 

I hated my life then, but I’m so grateful my dad cut me off when he did. It taught me the value of earning a living. If he hadn’t, I’m willing to bet my life would look drastically different today. I know I’d be earning a hell of a lot less. 

I liked my internships so much that I would’ve worked for free forever, if Tim (dad) hadn’t put his foot down. 

Since then, for me, making money isn’t about getting rich. Instead, for me, making money is about maintaining control of my life.

So often, we—or many of us—come to expect our parents, who we usually do little to nothing for, to support us indefinitely, and get mad when they can’t anymore. 

But I think it’s the companies we should be upset with. It’s not ok to expect someone to work for free, and even a few months is a long time to go unpaid. These unpaid internships have interned us out of jobs. It’s spiraled out of control. 

Fun Fact: Two-thirds of lifetime wage growth happens in the first 10 years of your career. If you don’t demand what you’re worth from the start, it sets the stage for a below average salary for years to come

When planning for retirement, many Americans think about their pay the way they used to think about the value of real estate or stocks: that it will always go up…

But once people hit midlife, the good times are over. The 40s are the peak earning years for most, when the median income for men working full-time hovers between $52,000 in their early 40s and about $54,000 in their late 40s. After that, median income barely budges—it’s still $54,000 for men aged 50 to 54. In other words, there is a 15-year plateau.




Success ebbs and flows 


In my early twenties, I thought that once I “made it,” I would always be “making it.” Whatever making it means anyway. By my late twenties, I figured out just because you’re at the top now doesn’t mean you’ll stay there forever. 

For instance, many companies treat jobs as gigs/projects today, which means they view everyone as temporary, even if you’re a salaried full-time employee with benefits. Even if you consistently deliver amazing results, you can get fired at the drop of a hat, just because your boss doesn’t like your personality. It’s totally legal to do this. 

With this in mind, I HIGHLY recommend diversifying your income. Don’t depend on any one income stream for your financial livelihood, because you’ll be one layoff away from a catastrophe. 

Also, always be skeptical. Pay attention to signs. There are always signs something—like a layoff—is coming. And build “safety nets” in case you do get let go with no severance. 

For instance, always be networking, stay active on LinkedIn, guest blog/blog to showcase your expertise, then work will always be flowing to you, which is invaluable, especially when the hard times hit.




Your twenties are not the best years of your life


I hate to be the bearer of bad news, but most of your twenties will probably be stressful AF, lonely and depressing, or at least that’s how mine were in the grand scheme of things. And I’m not some weird, emo anomaly either. According to Business Insider, the majority of Millennials are lonely, burned out and depressed

Society tells you though that these are the best years of your life. Live it up now because you won’t be able to do anything later. First of all, you can do whatever you want your entire life, not just before you turn 30. I don’t know why this is so hard for people to grasp. 

While most Millennials love to brag about how many countries they’ve visited, I’m absolutely fine about having traveled only within the U.S. for the last decade. Personally, the whole backpack across Europe by yourself sounds dangerous, lonely, and stressful. 

To me, it makes way more sense to stay put (traveling is stressful and time consuming), work really hard, get my worth up, find someone I love, and THEN go stay in a really gorgeous hotel and really enjoy/experience wherever I’m visiting later in life. 

The people backpacking through Europe, who are so happy and cool on Insta, will likely pay the price in lost wages and their career trajectory won’t be anywhere near as bright as someone who focused on working hard in their twenties.



In the words of Gary Vaynerchuk, no one ever bought the Jets by taking a vacation to go skiing in their twenties. 




Track your life

The first thing I remember officially tracking is my productivity. I got this Mac app, called Timing, which tracked how much time I was spending on the computer working. I remember being shocked that I was logging 12 hours of screen time per day most days—even on the weekends. 

This unhealthy lifestyle obviously made me gain weight, but I didn’t even realize it until I started tracking my time on the computer. 

Now, I track just about everything. Doing so keeps me honest and forces me to maintain good habits, like going to the gym and taking breaks/walks throughout the day. 

I highly recommend tracking your life as well, especially the things that are hard for you to do every day. 




Life is fragile and short

It’s amazing how fast life accelerates as you age. Years happen in the blink of an eye. No lie. And the older you get, the realer stuff gets. 

Getting married and having babies are the big life events that everyone talks about; what no one talks about is that friends and parents start dying, and it can be really surreal. It definitely makes you realize how short and fragile life is. 

Two people in my immediate friend group died this past year, and it was shocking and sudden—both from crazy, random accidents. 

My first point is: Stop acting like you’re invincible. Pay attention when you drive. Don’t be overly reckless. No one is promised to be here tomorrow. 

My second point is: Don’t waste your time dating around if you’ve found someone you truly love and have a great time with, because your time here could end any minute. 

Take this heart-wrenching Modern Love column I read the other day. The writer waited eight years to finally talk to the man on the subway she eyed on her daily commute. After nearly a decade of not hanging out, they move-in together, get married and have two sons. 

Not long after, her husband leaves one day, and never returns. He dropped dead out of nowhere due to a blood clot or something. 

It just kills me a little inside that they didn’t get together sooner, so they could’ve spent even more time together—with their person. 

So stop being hard. Don’t pretend to not care. Don’t screw around, because you think that’s what you’re supposed to do. Do you.