Best advice to twentysomethings: trust yourself

Best advice to twentysomethings: trust  yourself

Best advice to twentysomethings: trust  yourself

During my twenties I played in beach volleyball tournaments with Olympic contenders all the time. You’d think this would mean that I love watching beach volleyball in the Olympics. But actually, watching makes me sad.

After college, I moved to Los Angeles, determined to play on the professional beach volleyball tour. People thought I had completely lost my mind. I gave up an invitation to study history in Yale’s graduate program. I gave up a job offer in New York City publishing. I gave up living in Chicago, where my whole family was.

Here’s what my day was like: I woke up at 7am and I walked to a bagel store. I ate four bagels because I had no money for food and I had to eat cheap calories that would hold me over until the end of  the day.

I rode my bike seven miles to the beach. I played volleyball for six hours. Then I rode back seven miles, showered and went to work in a bookstore for four hours. After work, I went to the gym for two hours. I did a twenty-minute aerobic warmup and then I lifted weights and then I meditated for twenty minutes where I visualized doing the drills I would do the next day on the beach.

I walked home after the gym and I read for two hours. Then I went to bed.

It was the same every single day. For three years. You’d think that other parts of life would get in the way, but here’s an interesting thing about having no money: there is no room for error. I planned every day so I had exactly enough money to eat, sleep and play volleyball. There was nothing else.

I made it to the tour. I was an internationally ranked player. But I thought I was just getting my butt kicked. I told myself my efforts were useless because I’d never be in the top five. I didn’t ever say, “Holy cow, I’m in the top 25.”

I thought I was a complete loser and I would never pull things together and I was mostly hiding from people so they didn’t see how messed up I was. I didn’t earn very much money, I didn’t do things that I thought a normal woman in her 20s would do. I was completely focused on beach volleyball.

Then, later, when I realized that I had actually been doing a good job of managing my life, I realized that most people in their 20s are worried, at one point or another, that they are messing up their lives. Especially people who take alternative paths. Yet, it’s the alternative paths that give people the most control over their lives as they get older.

I had a job in a bookstore because it’s the only job I could get that didn’t interfere with volleyball. But in fact, a job in a bookstore is great for someone with Aspergers. I catalogued all the books in my head. People left me alone to sort and shelve books. I read them as I went through the alphabet. In between the m‘s and n‘s was a special spot at the bottom where I put books I wanted to read that week.

The conversations I had with people were very limited in scope. I made change for a twenty. I made a joke to someone looking for Shakespeare in fiction. I made a recommendation to someone for a book that’s like The Rachel Papers (if you’re wondering: try Portnoy’s Complaint). I thought the job at the bookstore was a major disappointment for me and everyone who ever tried to help me pull myself together for adulthood. But in fact, the bookstore was a great place for me. I loved that job.

And I loved the repetition of training for beach volleyball. I did 200 jump serves every day. People wondered how I learned to set so well in just a year. It’s because I practiced, by myself, with fifteen balls, for hours each day. I had never worked so hard at anything in my life. But I didn’t see it that way—that I was completely focused and determined and hard working. I saw myself as lost.

But really, now I see that the hard work gave me confidence that I could accomplish whatever I want by working very hard to get it. Volleyball also taught me that if I want something difficult, there is no way to get it without being completely committed. I didn’t half-ass anything in my adult life because I saw women do it playing volleyball and I saw it made everything a waste of time.

Now I see that I spent my early twenties doing amazing stuff that was perfect for me. I read whatever I wanted to because there was no one telling me to stick to a syllabus. I made my own reading plans: metafiction, magical realism, minimalism. I was in love with what I was learning at night. I was in love with what I was learning in the day.

I did not have friends. I did not have money. I did not have the things I expected to have. But all that would have been fine if I had only had self-confidence.

I made great choices for myself after college. I read. I played sports. I spent time alone. This is all stuff I had been dying to do that I couldn’t do in school. I learned about what I wanted in my life by letting myself choose anything in life. It turns out that I chose great things for myself.

As an adult, I really appreciate the time I took to find out what is right for me. I don’t have that life anymore. I have kids now. And I have to earn money. And I had to scream at them six times just to get mental space to get this post written.

In the end, I left volleyball to write full time. Volleyball got boring. I am not a play-eight-hours-a-day kind of girl. Those women in the Olympics, they can play and play and play.  When I watch those women I admire how determined they are. To them, winning is everything, and they never let up. I was not like that.

But that’s not what upsets me. What upsets me is that I was not fine with who I was. I was a woman who worked really hard at volleyball and went home to read. I was a woman who needed space and time alone and loved routine. I was a woman getting to know myself. I wish I had felt strong and proud while I was doing that.

“What should I be doing now?” is a question I get a lot from people in their 20s. The answer is that you should be respecting yourself as you learn about yourself. You should give yourself the space to do anything and then look closely to see what you enjoy. You do not need to get paid for what you enjoy, but you need to find a way to commit to what you enjoy, and then use that as a foundation to grow your adult life.

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  1. David Yakobovitch
    David Yakobovitch says:

    Be strong and proud. Be yourself!

    Exactly! Thank you for this advice Penelope! I have spent much of the last year (22 years old) finding myself and doing what I want, trusting my intuition, and making moves in my personal and professional life.

    That SELF-CONFIDENCE will set you apart so much! You know it, and I am learning it very fast! Far too few people have self-confidence or awareness about themselves and what they truly, truly want.

    • Avodah
      Avodah says:

      @ David- I couldn’t agree more. Sometimes people consider self-knowledge, self-esteem and self-awareness to be part of the “California Cult of the Self”. However, knowing what one wants and knowing one’s self are crucial to success.

      I spent a large part of MA degree learning about jobs outside academia, informational interview, meditatiing and journaling. Even though I chose to pursue a career outside academia, these activities have helped me to know my strengths, passions and goals. I am a better private-sector employee bc of it.

  2. Dl
    Dl says:

    Beautiful post. It applies to everyone, not just twentysomethings. Most of us lack confidence as we pass through each stage of our lives. Later, when we look back, we see we were doing okay and wonder why in the world we worried so much. It’s the journey, not the destination that counts.

    • Penelope Trunk
      Penelope Trunk says:

      It is so true that each stage of passage is jarring to our self-confidence. It’s like starting over again and again.

      But I think the first time I did it, in my twenties, it was so hard that I would never even have believed that it happens throughout life. Once you do it the first time, other times get easier. Not because they are easier, but because you have more faith that you’ll get through it.

      I think I am going through a transition now. And I remind myself, again and again, that in my twenties I should have had faith in myself to make good choices. It would have felt better. And it was deserved. So it’s definitely true now: I just need faith in myself.

      And now that I’ve done this a few times, I believe it.


      • Will
        Will says:

        It seems to me that this post is saying that you don’t need confidence in yourself. Maybe it would have been more comfortable, but you made a good set of choices and everything turned out fine.

        Is this another excuse to beat yourself up? To agonise over the fact that you didn’t need to agonise? Perhaps it’s the mental equivalent of an invigorating light whipping with birch twigs when you come out of the sauna. And why not?!

  3. DeAngelo Jones
    DeAngelo Jones says:

    I’m 28 and between careers. This is the advice that I needed right when I needed it. I love baseball. I could play, watch, read about, and write about baseball all day. I’m going to take this time away from the 9 to 5 grind to find my niche in baseball and pursue it with all my heart. If I don’t do it now, I’ll regret it forever. Thank you for the kick in the rear.

  4. chris
    chris says:

    Yes, trust yourself, even when you or others perceive you are making a mistake(s). Mistakes are part of it, part of the triage, the sorting out.

    But HOW (step by step) can you talk yourself into believing in yourself and having confidence, if you don’t. If self-confidence is
    not natural to you. If self-doubt is more natural to you, how do you inch towards confidence and trust in yourself??!!

    • Miles
      Miles says:

      I think one way to build self-confidence is to look at your accomplishments. Look back and assess where you’ve gone in the past year or so. How much did you learn? What did you create? How much money did you manage to save? Taking stock of my accomplishment allows me to feel like there is some forward momentum to my life, that there is growth.

      • Adria
        Adria says:

        Perhaps you should allow your self-confidence to grow naturally, each day as you respond to self-evaluation questions such as: Did I support myself and my dependents spiritually and financially today? Did I share something today with someone else? Can I honestly evaluate myself and my actions?

  5. Sarah Fowler
    Sarah Fowler says:

    Penelope, it’s uncanny how often you write exactly what I need to hear. I am 25 with my own company, working my butt off but doing what I absolutely love for a living and being my own boss, which I thought I was going to have to wait until my 30s or 40s to do. I was beginning to think maybe my friends and family (and strangers!) who tell me to slow down were right, but nope – my life is AWESOME and I don’t want to change a thing. Thanks :-)

  6. emily
    emily says:

    Three more punch in the gut stories about learning to love yourself:

    Jeanette Winterson’s – Why be Happy when you could be Normal

    Lidia Yuknavitch – The Chronology of Water

    Pam Houston – Contents May Have Shifted.

  7. Helena Bouchez
    Helena Bouchez says:

    I totally agree with this post. I spent nearly all of my 20s in art school. Actually, I attended three art schools in 10 years.

    I cannot begin to express how messed up my family and friends thought I was. They thought I couldn’t finish anything, when what was really happening was that I was taking the time to do what I set out to do, which was to get an education. Which to me was different from the process of collecting courses like box tops which you submit at the end for a prize (diploma).

    Someone always will think they know better than you what what you should be doing. Knowing who you are and what you value and stating it, living it, with every cell congruent, is a good way to neutralize or repel those people.

    Thanks for this post, Penelope.

  8. Debt Free Teen
    Debt Free Teen says:

    Couldn’t agree more! Sometimes when success in a certain area becomes “normal” we forget how far we have come and become unsatisfied. It’s important to keep a good perspective and have friends around us to remind us how lucky we are to be doing things we love!

  9. Mildred Talabi
    Mildred Talabi says:

    Brilliant article Penelope – during the last Olympics I experienced a similar sort of sadness watching the athletics 100m & 200m which were my races when I was younger. Only difference is I didn’t put in half the hard work and persistence into it as you did with your volleyball, neither the length of time, so I didn’t come away with as many lessons!

    But I do agree, the discipline of committing to something, anything, and seeing it through is priceless in preparing you for life, and what better time to do it than in your 20s?

  10. Jon Putnam
    Jon Putnam says:

    Fantastic article – I am in my early 30s, and I grapple with this question, particularly now that I am out of my 20s. I have a stable life, wife, soon-to-be child, job, and so on, but I have had relative stability since I was 22 or so years old. I don’t feel like I had the time you describe and I feel it is awfully hard – nearly impossible now – to go back.

  11. Karen
    Karen says:

    Wonderful post.

    I think there is something about spending two decades in our education system being infantalized and talked down to that destroys self-confidence.

    It’s not how humans evolved to be.

    For virtually all of our history, the average 7 year old could contribute to the survival of the family unit (by foraging.)

    By their teens, they contributed as much as any elder.

    In this culture, we are “losers” until we hit our strides well into our thirties.

    I think this makes for a lot of psychological sickness (that is all but invisible, because everyone suffers from it.)

    • Isabelle
      Isabelle says:

      What a great point, Karen! I’d never thought about it that way before. That idea makes me even more determined/excited to make sure my kids contribute to the household and learn real, practical, useful skills.

    • Penelope Trunk
      Penelope Trunk says:

      I love this comment, too, Karen. And I realize, more and more, how related my homeschooling blog is to my career blog. We understand our career problems so much better by understanding how we were trained, in school, to have a career.

      We think we were not trained at all. Like, it’s almost a cliche to talk about how school does not train you for work. But in fact, when someone convinces you that you belong in a row of desks, that you should look for the answer the teacher wants, that you should follow all the rules, etc, then school is teaching you how to do work. It’s just teaching you bad habits.


      • Marita
        Marita says:

        I agree with school teaching us bad habits and even making us feel like invalids unless we go to college and get a j o b.

        I ask my daughter every now and then to earn $50 without getting a regular job. The first time I asked her she thought I was out of my mind!! But it has taught her that she can earn money right here and now and also how to go out and create an opportunity for herself.

        She’s made that $50 with editing photos in photoshop, creating graphics and writing copy for a website. And she’s just finding a way to turn her passion into $$ – party planning!

      • Karen
        Karen says:

        You’re so right, Penelope.

        I always roll my eyes whenever yet another talking head bemoans our lost competitiveness since not enough American teens are going off to college.

        I always wonder why no one ever takes the counter position:

        What if sending everyone to college is part of the problem?

        We’re forcing hundreds of thousands of our best hopes for the future to waste four, seven, or more years learning stuff they’ll never use.

        And what of the opportunity cost? What might those smart, energetic people have done with all of those years, if they hadn’t been mortgaging their future to cram for “required classes” taught by minimum wage adjuncts?

        Matt Tabibi memorably described Goldman Sachs as a “great vampire squid wrapped around the face of humanity.”

        But I think that metaphor better describes our universities and the so-called “banking” activity associated with them.

    • Karen
      Karen says:

      Glad it was useful.

      I’ll share an idea I heard from a friend, who has three kids still at home. He tells them that whatever they want to do in life, they have his complete support. But each of them must start and run four (yes, FOUR) businesses before they graduate from high school.

      He doesn’t care what the businesses are — mowing the lawn, selling stuff on eBay, or anything else they can come up with. But they must make at least a little money, and the kids must be in charge…getting a job does NOT count.

      He is determined that his kids have a comfort zone around living by their wits, being in charge of others and being an owner — and NOT comfortable hoping for a chance to follow someone else’s orders.

  12. Maria
    Maria says:

    Thank you, Penelope. Sometimes this is good to hear. I’m just turning 27, slogging through a long graduate degree (worst idea ever, in your opinion!), and finding that the things I love most about it are probably things that will lead me away from academic jobs, which is fine with me. Obviously this makes me wonder if I should just drop out now and start looking for jobs, and I fear that later on I’ll wish I had!

    On the other hand I love some aspects of what I’m doing now, I have a flexible schedule and lots of room to experiment with developing skills, my husband’s stuck in our small city for 2 more years, and I’m getting paid to be in school for the next 2 years, so giving up all of those things in the hope of landing a good job before wasting too much more time is something I still can’t bring myself to do. So I really hope it all works out, and my choosing the quality of life stuff during my 20s is not something I’ll regret in my 30s. Nice to hear that it wasn’t for you, only wish someone had given you words of encouragement too.

    • Cheryl
      Cheryl says:


      One advantage to getting your degree is that it shows employers (or investors if you start your own business) that you have a history of finishing what you started.

      I think that an employee having a degree is an employer’s face-saving ploy in case the employee doesn’t work out (“But he had a degree!”).

      Good luck to you!

  13. Jenny
    Jenny says:

    Great post. I love the way some wise person put it … if you could look at a roadmap of your life, you would just see that all those things that you were afraid of were just leading you were you needed to be.

  14. omar Lewis
    omar Lewis says:

    I really liked this post because i can relate to a lot of the things she was saying, i too had a difficult time perusing a sports career. at time it can be very lonely having to keep focused and in my case not being able to do a lot of stuff your average 19 year old would do. but you get though it as we do, and when it all comes down to it, you learn something about yourself. you find a inner strength that you somehow never knew you had until you pushed yourself.

  15. Michael
    Michael says:

    Apparently you werent loaded down with college debt like most students are. Life was easier decades ago. Try and do that now.

    • Penelope Trunk
      Penelope Trunk says:

      Be careful about the excuses you make for yourself. Most college grads will have that debt for a long time. So making all your decisions because of the debt will really limit your life.

      Instead, here’s another way to think about it. You will have the debt most of your life, but you can go through phases when you pay it down and phases when you don’t.

      You can get a forbearance if you do not have income. So you could definitely do what I did. You could write Sallie Mae a letter and say you can’t pay now, and they will work with you. They wouldn’t do it forever. But you wouldn’t choose to earn sub-minimum wage forever either.

      It’s not right that the college loan programs are a scam. But it’s also not right to use it as an excuse for you not living a life you want.

      That said, if you are not devoting your life to something like volleyball already, you probably have no desire to do it, so you are not being held back from it by loans.


      • Michael
        Michael says:

        I am definitely not looking for an excuse.. I have a full time job in silicon Valley one year out of school paying 6 figures. What I dont appreciate is how flippant you are about whats going on. Plenty of my peers are in deep trouble. Volleyball, nor finding who they are is the last thing on their mind and you may not see it because you are helping people with their resumes for 250 dollars.The economy is getting worse. Why dont you give advice for all those who cant afford to do what you did decades ago. Talking about excuses, Do I have to read about your malady every post? This blog is a front to sell your services. Why dont you go play volleyball for a few years. What beach in California do you want to meet at, since you fly out there constantly to get your hair done. Sorry, but I dont pray at the altar of Goddess Trunk. And, I didnt even need one of your 250 dollar resume reviews to get a job and I left school with no debt whatsoever. I worked and worked and worked and left school having them owe me money. Didnt even need a resume to get my job. Maybe you should write about people like me. I found myself alright. Found myself in a potential heap of trouble like my peers if I dint get straight to my work, intern every year, get paid for my research and have companies bid for my full time employment. And, of course I didnt major in theatre or sports management. Gee, I should write a book.

        • Gwen
          Gwen says:

          And yet, you still read this blog regularly enough to complain about what you see in “every post”. If you don’t value the advice, why are you wasting time reading it?

        • Lucy
          Lucy says:

          Michael, if you have everything so sorted then why the extreme bitterness and need to prove yourself?

  16. Katrina W
    Katrina W says:

    Great post! Everyone told me my 20’s would be hard & they were. Really hard! But nobody told me to be present. I was so busy freaking out about (what I thought were) my shortcomings, that I never allowed myself to just be still for a moment to appreciate how strong I was becoming. I really wish I could go back to my 20’s, just so I could give myself a hug.

  17. Harriet May
    Harriet May says:

    I think I am starting to figure this out. Just. I broke up with my boyfriend and moved home with my parents. He worked too much and watched tv do he didn’t have to think anymore after a long day. I started a Facebook page for my dog, which sounds crazy, but I have met a great group of friends through it, and I use it to practice photography. I met a guy while I was running who writes for our local paper and he’s invited me to meet his editor because he found my blog online. I finally am figuring out who I am and what I want. But it’s still reassuring to hear that I might just be doing it right after spending so much time and energy feeling so lost.

  18. Maia
    Maia says:

    It’s so true. Whatever you are doing just enjoy it because that’s what you’re meant to be doing at this time. From my own experience, like you Penelope, I was also sometimes in jobs which I felt were going nowhere and I thought that they’re a waste of time, but with hindsight I can see they gave me the experience to go on to different things and learn about what I was good at, what I wanted to and didn’t want to do.

  19. Rachel
    Rachel says:

    I love magical realism and I love your blog so much. Your personal story and example is the perfect inspiration for me.

    • Penelope Trunk
      Penelope Trunk says:

      I’m glad you took the time to say that you love magical realism. Because now I know at least one person clicked the link, and I have to say that I spent way too much time thinking about what to link to.

      I started to link to Jeanette Winterson and then I got nervous that she is not, actually, writing magical realism, and really I was just a bad reader and couldn’t focus so it felt like magical realism. So then I got sidetracked reading lists of magical realism books, and thinking I had missed some good ones that I should read now. And then I got sidetracked on this site that has an explanation of Winterson’s brand of magical realism. And then I got this idea that I should write a bit more about magical realism so I could put all these interesting links in the post.

      And then I remembered that Maria Killam told me that when I put 1000 links in a post she doesn’t think anyone clicks them. Because when I link to her in one of those posts, she doesn’t get a lot of traffic.

      So I’m thinking I probably link to too many things in a post. But I feel so good knowing that all the stuff I love is sitting there, nestled inside my blog.

      And, by the way, here is a post I like of Maria’s. I love when Maria does rules.


      • Joselle
        Joselle says:

        One of the things I like best about your blog is all the links in the post. I click on most of them.

      • Rachel
        Rachel says:

        This is funny because I hadn’t actually clicked on the link. Now I have and have moved on to the rules for design. I liked rule #2 so much, I had to pause and come back here to say I totally agree. I despise non-useful cabinets.

        I have never been a link-clicker but this may have converted me and I probably will read that book to. It does look magical-realism-y to me. As well, when I was watching both the indoor volleyball and beach ball the other day, I thought of you, and probably a lot of your readers do too.

      • Mark W.
        Mark W. says:

        “So I’m thinking I probably link to too many things in a post. But I feel so good knowing that all the stuff I love is sitting there, nestled inside my blog.”

        I used to think you had too many links in some of your posts. I used to think too many links somehow “devalued” the “important” links – those links which could be considered important to the “message” of the post. Then it occurred to me that as long as I could read through the whole post (without clicking on a link) and still get its meaning, it didn’t matter how many links were present. I don’t think I should have to click a link while reading on the first go around. However, if there’s something that I need to get clarification on or looks interesting, I’ll go back and click the link.

      • Katy
        Katy says:

        I actually found your blog through Maria – I read her blog because it’s somewhat related to my “side job” ;)
        She linked to your post about how to know when to move for a job (being close to family is more important than we realize etc)

  20. whattosay
    whattosay says:

    I’m approaching the end of my 20s, and know the feeling of “messing up” my life very well. The big problem of our 20s (and you pointed it out) is that we have way too high expectations for ourselves. When I look back, I can see that my time at grad school has been very beneficial in many aspects – learning, getting to know myself, enjoying music, travel etc. Having a child filled my life with love previously unknown and hopefully changed me for the better.

    However, it is hard to enjoy and be completely content with what I’ve achieved, without realizing that I’m losing to my peers in career-building. Somehow, I feel a sting every time somebody posts their shiny new professional title on linkedin, and ironically, also when seeing cool photos from Peru or Himalaya. I’m always feeling that I should be doing that too, as I’ve seen myself that way a couple of years ago. All of that knowing that there are not the same people doing these things, and that you can’t have everything at the same time.

    I think that as the time passes, maybe the bar you settle for yourself is becoming more realistic, and you really get to understand that you’ve even exceeded it in a number of cases. And then, you start being proud of yourself.

  21. Bill Brent
    Bill Brent says:

    Hi, Penelope — This is one of your most honest posts, and I think it’s my favorite. I love this part:

    “What upsets me is that I was not fine with who I was … I was a woman getting to know myself … I wish I had felt strong and proud while I was doing that.”

    Yes, and that does not apply just to 20-somethings. I’m 52 and I still struggle with self-confidence and commitment. (I used to have more, but at those points I had a more secure foundation with a solid support team, stronger cash flow, people depending on me to pay them, etc.)

    Anyway, I think it’s a lifelong process. Our setbacks can grow us, but they can shrink us. And yeah, that self-trust seems to be the determining factor.

    Thanks for this. It’s just what I needed to hear today.

  22. karelys
    karelys says:

    I am in my mid 20’s and soon to have a kid. I needed this today to remember that even though everyone looks down on the way I’ll chose to raise my kid that I need to have confidence because I have done my research and deep down in my gut I feel this is right.

    And eventually the world will catch up.

  23. Clinton Wu
    Clinton Wu says:

    This is a great post except the title could also have been “Best advice to twenty and early thirty somethings.” I’m a 29 year old ivy league grad and college athlete. While most of my friends are in finance and consulting making a pretty good stable income, I have jumped from real estate to sports to startup tech – all to scratch curiosity’s itch.

    I ask myself quite frequently if I should have left that $300K real estate job because I was bored. Still have many moments of doubt so I go through many of the same mental battles on a daily basis. This quote really resonates with me, “I thought I was a complete loser and I would never pull things together and I was mostly hiding from people so they didn’t see how messed up I was.” I have many days where that’s what I feel but I also have many days where I think I’m invincible and wouldn’t trade my experiences for any amount of money.

    Here’s an old post I wrote about my Career ADD if anyone’s interested:

  24. downfromtheledge
    downfromtheledge says:

    It’s funny how we all flounder around trying to find our way, yet we each take that struggle so personally: “I am a failure because I don’t know where my life is going.”

    The advice you gave ‘parents of 20-somethings’ is what we should use on ourselves: have compassion for yourSELF, and tone down the judgment and pressure.

    Maybe failure is just life’s way of showing us what we’re NOT meant to be doing.

  25. D
    D says:

    Upvotes for Portney’s Complaint.

    In my twenties I followed a kind of unconventional career path as well, though not by choice. I had a music degree but realized I liked business and wanted to work in corporate America. Alas, no one would hire me. Eventually I started my own company and it all worked out. Now you couldn’t pay me enough to work in big business.

  26. Kari
    Kari says:

    Thanks, Penelope, for reassuring us by telling your own story. It’s tough, but I’m giving myself permission, permission to stop hiding, to stop apologizing, and, above all, to show others that I’m happy with what I have chosen. I let them be happy for me, too.

    I love this photo of you! I played libero in high school and know that face well.

  27. channa
    channa says:

    When I was 22 I shared an office with a 35-year-old woman. She was the first one to tell me that pretty much every woman is much are happier in her 30s than her 20s. I’m so glad she mentioned it to me because it seems so counter-intuitive but it has proven so true for me and my friends.

    In your 20s you have less confidence, less financial security, less relationship competence, less assertiveness, less practice at life in general. Meanwhile movies, magazines and the whole advertising industry are telling you that you should be living an amazing, confident lifestyle that is basically fake. By the time you reach your 30s you’re just better at living and you understand reality. You’ve got your 10,000 hours of practice on all of the major things you do in life.

    So you’ve accepted that what you were doing with your life in your 20s was the right thing to do at the time, but you shouldn’t regret the way that you were feeling at the time because that was also part of the process of the hard work to get to the reward.

    • victoria
      victoria says:

      Agreed — and I think hormones have something to do with it too. As a teenager or twenty-something I was much moodier and more unsettled; now that I’m in my early thirties everything’s just much calmer and even keel.

  28. Mary
    Mary says:

    I am fresh out of my 20’s. What makes me so sad is that everyone in my life thought I had tons of confidence yet I had so little. I wanted to write and work in the adult industry but I was consumed by doing ‘the right thing.’ I made myself crazy until I was 28 and I realized that there is no right path, so I might as well do what I want. I wish I could have had the confidence to do what I do now, back when I was younger.

  29. Christina
    Christina says:

    Penelope this is where I come when I am depressed-scared-worried.
    I sneak to Penelope Trunk where all gloves are off. All souls are bare and I feel at home.
    This post hits HARD. And is bigger than my 20s. That lost self confidence when I rocked, translated to a decade (my 30s) lost in domestic court & my early 40s.
    I read this thinking: I’m back there-might as well be 20ish since my ruins left me in that same “oh what the hell, nothin to lose” place I had then.
    This post is for me in 40s as much as 20 somethings-only you readers have way more room to breathe–and no kids. Go: kick your fears in the teeth and have fun with it every day-because you CAN.

  30. Kayla Ramiscal
    Kayla Ramiscal says:

    This was a great read – I’m 22 and I’ve been having trouble because I keep feeling like what I’m doing isn’t… “right.” (I moved to Australia for a man I love and because my visa is being processed, I can’t work so I stay home most days and read and read and read… and blog). But I’ve been going non-stop since birth and this has been a great opportunity to just be. This post made me feel better about my decision.

  31. sarah
    sarah says:

    Trusting our own choices. It’s a simple concept in theory, yet rather difficult in practice. Why is it so difficult?!

    We all possess intuition and if we were taught to trust that at a very early age, rather than taught to dismiss it, I think many people would be living very different lives – lives that are much closer to that of the true self, rather than lives that align with what society or external expectations impose on us.

    This was a very reflective, honest post. It’s subtle, but I can sense in your writing that you’re going through a transition. The quiet vulnerability in this piece is lovely. Thank you for sharing.

  32. suyen
    suyen says:

    Thanks for this post, Penelope! I really felt like you were speaking to me. I’m about to enter my 30s but I am still working on being more confident. I sometimes feel lost, too, and maybe the way I envisioned myself to be at this age is just different from what is actually happening. But I realize that it should be okay. Maybe this is really where I am supposed to be at the moment. You made me remember what Steve Jobs said in his Stanford commencement speech: that you have to trust that the dots will somehow connect in the future. It is always in hindsight, though.

  33. Jen
    Jen says:

    This post was intended for Gen Y, but there is a message here for Generation X. It’s an epitaph buried in subtext, like a screenplay that doesn’t know it’s asking a question and not providing an answer. Here lies the youth of Generation X. Whatever space we had we mistakenly took for wasteland. There are things I don’t like to watch, too.

  34. Aruna
    Aruna says:

    I am a woman in her twenty somethings and this post is exactly what i want right now in my life. Thanks for posting this!

  35. Sadya
    Sadya says:

    “Not all those who wander are lost” J.R.R Tolkien said that in the Lord of the Rings. We mistake feeling lost for being lost.

  36. lisa richmon
    lisa richmon says:

    one of these days you’ll come to virginia beach to speak and this wil be the kind of message you’ll share. i don’t have kids but plenty of my friends and their kids (and my clients) will benefit from hearing these kinds of stories.

  37. steve wille
    steve wille says:

    Amazing. Check out a book called Dying To Be Me. The author came back from a deep near death experience with exactly the same conclusion. The best way to get where you are supposed to go is to be present, love who you are and live your own truth fearlessly. Energy spent on being who you think you are supposed to be is a waste and sends you in the wrong direction. Not trying to promo the book, just was impressed with how it reinforced this post. Author is Moorjani.

  38. Terry
    Terry says:

    I was beginning to despair that you would not write something about beach volleyball during the Olympics. This was much more than I expected and, as usual, interesting in surprising ways.

    I think you have a column devoted to NOT doing what one loves, and there is contradiction between that one and this one. That said, I certainly believe that one can and should ask oneself what one is learning doing any pursuit, and no one should ever sneer at self reliance.

    (I also click on the links).

    • Penelope Trunk
      Penelope Trunk says:

      Oh, I’m glad you brought up the doing what you love thing. I did not make enough money in the life I was living. So I learned what I love to do, but I did not learn how to support myself. I think the difference is really important.

      For example, from this life that I describe, I learned that if I don’t read for about an hour a day I go nuts. Reading is a way for me to rest my brain. I don’t need to get paid to read because I have to do it for myself whether or not I’m getting paid, (though it’s likely that reading will always be part of my job).

      Something I didn’t write about in this post is that I realized I was better at marketing myself than almost anyone on the tour. So I decided to do do marketing for a living.


  39. Claudia
    Claudia says:

    If I were to follow your other, previous advice on life stages, wouldn’t I be frantically searching for a husband in my early 20s instead of playing volleyball, so that I could have a baby by 25? (That being said, I still enjoyed this post.)

    • Penelope Trunk
      Penelope Trunk says:

      I’m sure you will not be surprised to hear that playing beach volleyball is a great way to meet a lot of men. But that is beside the point…

      At the time, I was very conscious of the fact that I wanted to be living with a guy and I wanted to be set knowing who I would do my life with. But I didn’t feel like anyone would respect me if I said that. It was completely unacceptable at that point to say you wanted to get married and have a family. It honestly never occurred to me that it would be okay to do that, which is why I’m nuts about telling women that if that’s what they want in their 20s it’s okay to focus on that.


      • Breana
        Breana says:

        I know this is what, 2 years since the original comment but I’m curious. If a woman is in her twenties and really wants to get married how can she go about trying to do that? I mean, it’s not like she can make it her job to search for a husband, even though she may wish she could do that. What would you suggest?

  40. Stephanie
    Stephanie says:

    Thank you. I´m 24 and I hate what I do because I´m trying to be a grown up. I don´t have kids, I have a family that supports me and I was confused. Till I read this. Thank You. I will enjoy what I love to do. :)

  41. sukeina
    sukeina says:

    What about a 40 year old who took the conventional path expected of her and now is regretting her choices? Married young (at 21), has a wonderful family (3 kids–ages 14, 10, 8) and a loving spouse, but can’t seem to find contentment. She is a PM–sort of fell into the job, enjoys it, but feels like she has missed out on many experiences in life….wants to travel more, but finds it too expensive with a family…
    Love the post, but yet it makes me feel regret and remorse for doing what I was “expected” to do….

  42. zan
    zan says:

    ah, penelope; sometimes, you nail it. i’m (happily) long past my 20’s, and (more happily) long past my twentysomething (and thirtysomething and fortysomething) discontent. in retrospect, i did everything i needed to do to become who and what and where i am now…which is (with financial exception — but i’m working on that) almost exactly who/what/where i always envisioned.

    and, especially in these economically challenging times, this is one of the most valuable observations you make: “…here’s an interesting thing about having no money: there is no room for error. I planned every day so I had exactly enough money to eat, sleep and play volleyball. There was nothing else.” in my experience, that’s how we discover the deeper realities of life — and the deepest truths about ourselves.

  43. Elizabeth Crook
    Elizabeth Crook says:

    What a great post to read during the Olympics. I agree that your 20’s can be full of inner turmoil, when that time period should be led by exciting self-discovery. Hindsight is 20/20!

  44. Robert Shaver
    Robert Shaver says:

    So what’s your best advice for a sixtysomething that could retire but want’s to do something new that might make an impact?

    • chris
      chris says:

      From another sixty-something . . . VOLUNTEER somewhere, doing something you’ve always wondered about, or imagined you would like to do. Do it as a lark, with no monetary or other expectations. You are trying something new. You are experimenting. You are winging-it. You are bold. Boldness and self-confidence are almost indistinguishable.

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