The best is yet to come.
Words: Dashae Engler
To properly say goodbye to my 20s, I took a trip down memory lane. I went through all my old notebooks — cringing, crying, and laughing at my writing.
What really hit me was something I wrote back when I was 23: “the idea that I can have a fulfilled life seems unlikely.”
But I wasn’t unfulfilled — I just felt rushed. Aging felt like a countdown — like if something didn’t happen in my 20s, it never would. If I’m being honest, when looking at the goals I made for myself, I don’t know who some of those were for. Maybe my parents, friends, society — but certainly not for me.
I know I’m not alone in that feeling, so I talked to two 30-somethings who are reshaping their own ideas of success. They’re not the blueprint for hacking your 20s or 30s, but I hope their stories constructively challenge you — they sure did challenge me.
Be Intentional
Cultivating a life path takes intentional time and effort. Billy Weathers, founder of The B. Wells Foundation — an advocacy group for young creators in Des Moines, Iowa — wasn’t afraid of getting older.
In his 20s, Weathers’ focus was grinding and creating success for himself — something he’s still doing in his 30s. His story reminds us that our 20s are about setting ourselves up for success, not for achieving everything.
“Not to be a pessimist, but if you weren’t doing anything in your 20s, it’s not really going to shift in your 30s,” Weathers says.
As a recording artist, lounge owner, and CEO, Weathers has always loved the hustle. Now he sees that success isn’t a specific goal — it’s having flexibility when defining success.
Being intentional is key at any stage of life, it doesn’t just click when you turn a certain age. Setting aspirations now will prepare you for the future. It’s kind of like falling asleep with your makeup on — it’s cute in your early 20s, but eventually you’ll need to do better.
“Ask yourself why you’re doing things, why you’re hanging out with certain people, what’s your focus, or what do you just want out of life?” Weathers says.
“Success isn’t a specific goal — it’s having flexibility when defining success.“
Maybe by the time you hit 30, you plan on getting married, graduating from college, or landing your first “adult” job. Sometimes, we think we’re ready for certain goals, but they don’t always happen on the timeline we create in our head.
The Security of Goals
You might have to wait on or even sacrifice some smaller achievements to reach your biggest ones. Take time to sit with yourself and ask what you really want. Maybe you’re not passionate about being a parent and you’re just listening to outside opinions. Allow a pause to decide what you want your 20s, and the rest of your life, to look like.
“I have a lot of friends that went the family route. I think that all of your focus goes towards raising a child or dedicating [yourself to parenting],” Weathers says. “I drastically chose the opposite.”
Do you want to go back to school? Or is that what your parents want for you? Are you ready to settle down? Or are you not the marrying type? Have you always dreamed of being a parent? Or do you want to be the cool and mysterious auntie or uncle? This is what your 20s are for — to decide what you want.
“Having [goals] you can lean on to feel in control during an obstacle or challenge gives [you] a sense of safety,” says Tj Scott, a mindset mentor in Des Moines, Iowa.
Pick out goals that serve you. Then you can start actualizing and editing them. This is your life, not anyone else’s — and you rarely make the wrong decision if it’s informed. But that doesn’t mean you should play it safe — push yourself to do things that challenge you.
If that calculus class has you rethinking your current career path, take a step back and analyze your goals. If something feels off, remember — there will always be another job, hobby, or person that fulfills you more. Just be patient as you navigate those obstacles.
Our 20s are weird
Theresa O’Keefe, a licensed clinical social worker in western Montana, says the 20s are just a “weird time” for most of us. It’s a decade of change.
“Some people, as they’re turning 20, are becoming parents [and] getting married,” O’Keefe says. “Others are barely shifting their life from what it was like living in their parents’ home or still living in their parents’ home.”
Typically developmental benchmarks are associated with adolescents who may be behind in reading or writing — but it differs in adults. The benchmarks that society has pushed on us look a bit like this: graduate from college at 22, land your dream job at 23, get married at 24, have kids at 25, and buy a house in between all of those.
Unfortunately for young adults, these benchmarks make us feel like we’re doing something wrong, no matter what we choose. It’s a complete paradox: if you’re not dating to marry — you’re not being strategic, but if you’re already settling down — you’re wasting your youth. If you work too much — you’re taking the fun out of life, but if you take a mental health day — you’re being lazy. It all seems a bit impossible.
If you feel behind, getting older can feel like a horrible experience. But O’Keefe says these standards shouldn’t be indicators of self-worth. These “benchmarks” aren’t everyone’s path.
Societal standards don’t consider an individual’s hopes, dreams, or conflicts outside of their control. So for many of us, turning 30 can feel like a nail in the coffin.
Rip 20s, You would’ve loved our 30s
Like Weathers, Janae Gray, 36, wasn’t concerned about turning 30. She was ready to turn the page and happy for the wisdom and experiences her 20s brought.
Gray’s a busy woman. She’s a marketing advisor to the B. Wells Foundation, a vice president of marketing and supplier diversity for Mittera, a mentor for the Big Brothers Big Sisters program in Central Iowa, and a small-business owner.
On Gray’s 30th birthday, she celebrated by pledging death to her 20s.
“Everything had to be all black. I felt like [it] was a death to my 20s,” Gray says. “Honestly, in a little bit of a celebration.”
She was confident about her 20s and excited for what her 30s held.
“If you’ve been able to manage [societal standards] pretty well … Thirty can be a little bit more of a rite of passage,” O’Keefe says.
Reaching societal standards wasn’t hard for Gray. For the most part, she did. The ones she didn’t meet were overshadowed by more important goals.
“If I wasn’t in a job that I wanted to be at, then adding kids wasn’t going to make my life any better,” Gray says. “I knew that I wanted to be in a more stable place myself and have hit the goals that I wanted to hit before adding more layers onto anything.”
The Subtle Art of Getting Older
I’ll probably cry when I turn 30. I don’t think it’s because I’m afraid, but because of my tendency to be dramatic. I hate goodbyes, but I also love hellos. We stan a contradicting cutie.
I’m in a much better place now than I was in 2019, crying over my old journals. I hope you are too. But don’t forget that you won’t be 20-something forever. If 30 seems far away or too close for comfort — being intentional in the moment will allow change, learning, and new experiences. If there’s one universal goal, it should be to keep growing into a better version of ourselves — for ourselves.
Getting older can be hard — I’m not the same girl I was at 19 — and I’m grateful for that.
“I hope I’m still changing in my 40s. Otherwise, it means I was probably doing the wrong shit in my 30s,” Weathers says. “I hope I still like me. I hope I’m still somebody I’m proud of and want to be around.”
A Guide for the Next Decade:
1.) Examine if your thoughts about falling behind are necessary — if you’re just being hard on yourself, throw them out and plant new ones. Eventually, those negative thoughts will show up less.
2.) View life in decades rather than years. This helps with goal setting while allowing flexibility for unexpected moments. When things get tough, remember that meaningful progress toward a goal often takes about a year.
3.) Be intentional in your 20s. Rather than staying in constant grind mode, focus on learning from experiences and creating new ones.
4.) You don’t have to say yes to everything. But don’t say no to everything either.
5.) Create goals that match your lifestyle. If you want to be at the top of your career but want to be an active and attentive parent, it will take more work than just choosing one. Decide what’s important to you at this stage of your life and make the time for it.
6.) Focus on your happiness, you don’t owe anyone anything. If you worry too much about what everyone has to say, you miss out on your own voice.
7.) Breathe — it’s going to be okay. You don’t have to do what your parents did or what your friends are doing.
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