27 Life Tips On My 27th Birthday

Is it possible to feel young and old at the same time?

Dillan Taylor
5 min readMar 2, 2021
A father and his son playing on the bed

27 is a weird, in-between stage of life.

30-somethings think I’m a baby. Meanwhile, to me, a 21-year-old might as well be 16.

In these almost three decades, I’ve lived both an exhilarating and a fairly boring life.

I have:

  • Attempted suicide
  • Acted in plays
  • Been in love
  • Had my heart broken
  • Broken a heart
  • Started my own business
  • Had threesomes
  • Failed out of college
  • Bombed while performing stand-up comedy
  • Started a podcast
  • Started a YouTube channel
  • Done coke in my friend’s bathroom when he asked me not to
  • Cultivated amazing relationships
  • Shattered relationships
  • Been punched in the face
  • Been punched in the chest
  • Been punched in the stomach
  • Lived in another country and learned its language
  • Tried a lot of things
  • Failed at most of them

Looking at them all together in one list, it sounds like a lot. But nowadays I spend my nights reading a fiction novel and going to bed at 10 pm.

I’ve learned a ton in my 27 years so far. Some of it intentionally. Most of it accidentally.

Here are 27 of my favorite lessons that you can hopefully use to live a more fulfilling life.

27 Tips

1) You will never regret spending an hour reading, working out, or calling a friend. You will almost always regret spending an hour scrolling on your phone. No one ever wished they spent more time on social media.

2) It is never too late to start learning something new: a skill, a language, a sport, anything.

3) A skill that anyone can benefit from is that of storytelling — through presenting, writing, or conversation.

4) You don’t owe everyone an explanation for everything. Example: You don’t need a paragraph explaining why you can’t hang on Saturday. Just say you can’t hang on Saturday.

5) Before you start diagnosing your problems, check your “health trifecta”:

  • Diet: What are you putting into your body?
  • Sleep: Are you consistently getting 7–9 hours each night?
  • Exercise: Are you doing strenuous exercise three times a week?

6) Keep a database of your friends’ recommendations and consume them over time: books, documentaries, podcasts, videos, and so on.

7) Being the flaky person who never texts back makes people see you as unreliable and even untrustworthy. If that’s you, put in the time to work on that now and save valuable relationships in the long run.

8) Pursue intentional value exchanges with your friends. Trade and share your skills: coaching, consulting, chess, nutrition, personal training, feedback. Find ways to help one another. It’s a lovely way to stay in touch and you become closer with the person as well.

9) Studies show that people typically don’t “find their passion.” The vast majority of people develop their passion by getting really good at something. Seeing progress in something increases interest in whatever that something is.

10) Before you send that important email or long text, write it as a draft somewhere else first. Read it aloud and make sure it’s free of errors. Then copy, paste, and send.

11) No matter what it’s about, if you’re about to send a super emotional text, wait until tomorrow. You will almost always calm down and realize that sending it would’ve only made things worse.

12) Every single person you care about will be gone one day. Call them. Tell them why you appreciate them. Travel to spend time with them. Make sacrifices for them.

13) Keep a calendar of your major accomplishments and memorable events. It’s cool to be able to look back and know exactly what happened in your life in August four years ago.

14) If you’re with other people, never have your phone out and face-up in front of you. In addition to watering down your interactions, it signals to others that they’re not your priority. You’re essentially telling them, “I’ll give you my attention, until I get a notification.”

15) Assume everything will take 1.5x longer than you believe it will. If you think it’s a 20-minute drive, give yourself 30 minutes. The worst thing that could happen? You’re a little early and you have extra time to breathe and prepare.

16) Write daily. You don’t have to share it with anyone and you don’t have to write paragraphs of captivating prose. Even if it’s just a single sentence, it’s therapeutic to consistently get your thoughts out on paper. Plus, it makes you more creative and articulate.

17) Keep a running record of all your favorite quotes: from books, podcasts, things your friends say, and so on. It’s fun to look back and see what and who has captivated you over the years.

18) When you feel stuck, write the answers to these three questions:

  • What are the most important things I should be focused on in my life right now?
  • What am I doing too much of that’s getting in the way of these things?
  • What am I not doing enough of to maximize them?

19) No one cares about what you look like at the gym. Everyone is just as insecure as you are and are more worried about how they look.

20) Discipline doesn’t have to be seen as a difficult chore. You can simply ask yourself, Am I putting effort into the things that matter most to me on a daily basis? This is how you trick yourself into doing uncomfortable things. You may not want to work out, but you want to be fit. Therefore, you do want to work out.

21) If you’re thinking about buying that concert or plane ticket, just buy it. The financial stress will go away. The memories you create with the people you care about will live on for decades.

22) Take a vacation once a month. It doesn’t have to be a weekend getaway. It can be just a Saturday trip to that hiking spot two hours away.

23) If you’re trying to build strong habits, start with your sleep. Anything you want to do in life will be much harder if you aren’t well-rested. And no, you don’t run fine on six hours of sleep; you’re just used to being tired. Change that.

24) Actively seek out conversations with people you disagree with. It’ll be uncomfortable, but staying in your own safe thought bubble is like never exposing your immune system to germs: It makes you weaker, not stronger.

25) Treat texts more like emails. Don’t feel insulted when you don’t get an immediate response. Being “on call” is a fairly new phenomenon. Your friends aren’t med students; they’re living their lives.

26) You don’t need permission to do anything. Create what you want to create. Learn about what interests you. Start that business. Launch that podcast. Ask that person out.

27) If you create anything with the goal of money or subscribers or other forms of external validation, you will almost certainly quit. Those things take a long time and if you don’t truly love the process, you’ll have nothing to keep you going.

These are some of the lessons that have helped me along my way. I hope they can help you along yours, too.




Dillan Taylor

Helping creators do their work, make better content, and grow an audience.