10 lessons I learned in my 20’s

Email readers: I’m so sorry about the link mishap on today’s email. Click here to go to the right post!


Email readers: I’m so sorry about the link mishap on today’s email. Click here to go to the right post!


Today is the day before my 30th birthday(!), so I thought it would be fun to reflect on the 10 biggest lessons I learned in my 20’s.

And since last week’s “Mini Edition” of The Lively Show was such a big hit… I decided to share the lessons I’ve learned with you via another Mini Edition of The Lively Show!

I’m sharing the lessons I’ve learned concerning marriage, business, uncertainty, and cultivating a beautiful home. 






  • The biggest thing I look for when buying something new.
  • How to start difficult conversations for the best results.
  • Why failing is a good thing.
  • How to get more of what you want.
  • What marriage means to me (aka: how I knew I wanted to marry Mr. Lively).
  • Why stuff and goals don’t really bring joy and fulfillment in and of themselves.
  • How I know when to stop doing something and go onto something new.
  • The biggest habit I’ve cultivated to create massive change in my life.
  • The number one lesson I’ve learned that I cannot wait to use in my 30’s.


Show Notes


The 7 Habits of Highly Effective People

Private Victory Habit

Why I married Mr. Lively









Photo and art direction by Becky Murphy

This Post Has 39 Comments

  1. Hey Jess, I’m listening to this one right now and I just wanted to let you know that there seems to be a few areas where your editing got messed up – there are a few repeats and sentences that seem to get cut off, etc. Just wanted to give you a heads up! I’m still enjoying it, nonetheless. 🙂

    1. Thank you! I just realized what you were talking about. Drats! I spent all day so far on this episode! I’m taking it down now to redo. Be right back with the udpated episode asap!

  2. Well, Jess, you’ve done it again. I just spent the last hour listening to your latest podcasts and loved it all. You are truly + amazing and inspiring and feel blessed to follow you! Have an amazing b’day. From one (me – the 10th) Libra to another (you) 🙂

  3. Early Happy Birthday Jess! I hope it’s marvelous! I like the idea of the one hour daily devotion to the mental, spiritual and physical. I stumbled onto this idea a few years ago out of a need to try to cultivate positive change. It’s quite rewarding for me personally and I’m sure that others will benefit from it too.

  4. What a sweet podcast to reflect on this past decade and share some wisdom with us! The “Why stuff and goals don’t really bring joy and fulfillment” was so true and hit home with me right now. Thanks again for sharing! I hope you enjoy your birthday, Jess!

  5. Such a nice podcast Jess. The difficult conversation starter definitely resonated with me and I’m going to try out your tip (well, hopefully I won’t be having any difficult conversations for a while but you know…!). Have a wonderful birthday and enjoy. I’m a Libra too (my birthday is Saturday) x

    1. Yes, hopefully you won’t have to use it soon, but at least you have it in mind if/when it might be needed. : )

      And happy (early) birthday!!

  6. I nodded my head the whole way through this podcast! Brilliant 🙂 I’m 29 too, but still have a few months left of 20-something lessons to learn. I really love your approach to marriage. I really feel the same way (though I’d never quite put into words, so thank you for that!) I’ll have to try you difficult conversation starter technique too. I think that approaching awkward convos from a place of honesty sets a great tone (and/or intention ;))

    Happy Birthday miss! I hope it’s a good one ^^

    1. That’s great to hear! Give that phrase a try the next time you’ve got something kind of scary to say. It hasn’t steered me wrong if I follow it up with a heartfelt truth.

  7. alexandra

    such a wonderful podcast. i’m a very new listener and for someone whos in their mid-twenties, this was relevant and interesting. thank you much for the part on marriage. for someone who’s been living with someone for about 6 months now, and together for over a year, it’s a hard subject sometimes, but you laid it out beautifully as i think i feel the same way. you have these friends “who just know” and have that voice that tells them that’s it! I havent had that yet. maybe when we hit a year under the same roof I will, but who knows… i do want him to be in my boat!! (plus, we’re nautical people, anyway!) happy birthday i hope you have a truly beautiful day!

    1. Aw, that’s great to hear, Alexandra! I’m glad you liked the part about marriage in particular. That was a hard lesson for me to learn, but I’m very grateful I got the message eventually. Go with your gut… but don’t necessarily expect it to give you a name. : )

  8. Megan

    I feel like a “I’m just going to be honest” print could be useful over my desk 😛

  9. Catherine Flores

    Happy birthday to a truly inspiring person! What a lovely collective of wisdom you’ve shared here! Sitting midway in my 30s (34!), I loved your lessons and examples for application both then and looking ahead. I agree with these takes – particularly on “exfoliating” (great word choice) what isn’t needed in our surroundings and on the all-important trusting of your gut and the private victory. Thank you for this, and for YOU!

    1. : ) Thank you so much, Catherine. I’m glad you could relate to a lot of them from your life, too.

  10. Bridget Wall

    Happy birthday!

    I sent this post from Lifehacker to the undergraduate students that I mentor, and a lot of them really loved it! I think we really forget some of the bigger things in life during our 20s among the chaos of everything, so any reminder is great!

  11. Such good stuff jammed into this little episode. Most people I know really rock their 30s because they’ve overcome a lot of their old insecurities and can really bloom! I’m a much cooler chick now that I’m in my 30s. 😉 And happy birthday, Jess!

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