What I Wish I’d Known: Women on the Most Valuable Lessons From Their 30s, 40s, 50s, and 60s

Big milestone birthdays have a way of changing our entire worldview. (Although sometimes they don’t, and that’s okay!) More often than not, though, entering a new decade of life brings with it a new type of clarity — a refreshed perspective about the past and even, if we’re lucky, a new way of seeing the future. That’s the point — and the blessing — of getting older, after all: gaining wisdom, knowledge, and experience through days clocked on this rapidly spinning ball we call home.

Another benefit of age is understanding that you don’t have to have direct experience with something to learn from it or appreciate it; you can really glean all sorts of valuable insights from other people and apply lessons from their lives to your own. As part of our series this month, we asked a handful of women of varying ages what they wish they’d known in the decade prior, and they didn’t hold back, with answers that are poignant, touching, and occasionally hilarious.

What I Wish I’d Known in My 20s

Your 30 are different from your 20s! I’m surprised by that. I thought it was just: You are a kid, and then you are an adult. I never thought about how almost all of your life is spent as an adult, and there are so many stages. I look back on the last decade with rose-colored glasses. I kind of wish 30s me could give advice to 20s me. I look back and see myself as brave and generous and creative and kind.

I wish I’d known that my positive attitude was my greatest asset and that I should do everything I could to protect it. I wish I’d known how transient people’s roles in my life were and are. People change jobs, people break up, people grow and change. Someone might be your boss or client one day, and you feel so much pressure to impress them, but then you get in a situation where you’re positioned more as an equal and a friend, and you see them differently. They’re just a person like you and everyone else.

Maya Angelou said, “Each time a woman stands up for herself, without knowing it possibly, without claiming it, she stands up for all women.” Teaching a university class and starting a business in my 20s taught me that my voice has power and that speaking up for what’s right makes other women feel like they have permission to do the same.

I wish I’d known that laser hair removal (and really any beauty treatment that’s going to save me time) is worth it. I wish I’d known to have a default nail color. Just get a ballerina gown dip polish every time. I wish I’d known that I could just get the car I wanted instead of feeling unhappy and self-conscious about driving an old, messy car. I love my little black Buick SUV with beige leather seats. I wish I’d known to spend my money and time on facials and exercise instead of listening to the women at the makeup counters trying to sell me something.

I wish I’d known that I can be the person who goes to early morning exercise classes. I didn’t see the point in waking up early, but I now see those hours as a gift to myself. I wish I’d known that procrastination is not laziness. I needed to look deeper to find the issue instead of blaming it on myself. Was I missing resources? Did I need help from someone or more information? I wish I’d thought without judgment about what was keeping me from doing what I wanted or needed to do.

I wish I’d known that if I didn’t want to be around someone, it didn’t make me a bad person. There was probably a reason something felt off, and it’s fine to trust myself and my instincts.

I wish I’d known that when I can’t stop thinking about something, I should just take action. It’s totally fixable if I make a mistake or regret my decision, but it’s a waste of time to ruminate. I don’t need to feel guilty about really leaning into doing things I love and indulging because it gets harder and harder to get in touch with what you want at your core. It’s not selfish to do what you want; that’s actually what really should be guiding you through life. As generic and clichéd as it seems, being yourself really is the ultimate goal.

I wish I’d known to go see Britney Spears in concert. It doesn’t matter how much it would have cost. I could have figured that part out.

ron galella archive file photos 2010

If you have the chance to see Britney Spears in concert, take it!

Ron Galella, Ltd.//Getty Images

It’s okay to be the bad guy in someone else’s story, no matter how much you’d love to control others’ perception of you or be seen for your true intentions. It’s not everyone’s path to see you in that shiny way. The funny thing about humans is we sometimes need a bad guy. A bad guy gives people someone to fight against so that they keep moving forward — until moving forward solely for the love of themselves, instead of as an act of rebellion, is actually enough. Remember that you’ve also needed others to be the bad guy in your story.

This is an important time to work on self-esteem and to surround yourself with people who have a strong sense of it for themselves. When we have low self-esteem, we can feel a bit powerless — and those who feel powerless tend to engage in a power struggle, even on a subconscious level. There’s something to prove externally because the knowing isn’t there within. Thus, you’re led to look outward for something others can’t give — not through recognition, and certainly not through competition. All the external praise and validation or “winning” in the world won’t change a thing. Our sense of worth must come from deep within ourselves.

Self-esteem comes from estimable acts, over and over again. It doesn’t come from self-care and face masks, although those are nice too. Actually building self-esteem in our 20s is the opposite of what we think it looks like. It involves boring, monotonous, even sometimes painful consistency, adversity, and responsibility. It comes from doing the right thing even when it’s hard, from going toward really difficult situations and conversations that reveal our character when our back is against the wall.

We waste so much time focusing on finding a solution to our problems, when we should be spending that time clearing our vision so that we can see the problem more clearly. When your goal is to truly see and understand the problem, the solution becomes undeniable. Life is more about seeking to understand than it is about seeking to solve.

What I Wish I’d Known in My 30s

I’m at a stage and age in life when I no longer apologize for saying no or “that doesn’t work for me.” Period. No explanation necessary. It’s the most freeing feeling. I wish I had this perspective 10 years ago. I had a habit of feeling guilty for saying no and would go out of my way to explain why I couldn’t rework my plans to accommodate others’ requests. That in itself is a lot of work. No is an acceptable answer.

Take a vacation! Use every single vacation and comp day that is available at work. Do you know how many vacation days I lost in my 20s and 30s trying not to miss something at work? What was I missing? Not a thing. The job will be there, and you are not a slacker for taking the time you’ve earned to rest and reset.

Sleep is underrated! It’s not healthy to operate on five or fewer hours of sleep. Your body and mind need the rest. Get a good nightly sleep routine, and be consistent.

It’s okay if you’re single longer than you planned on your vision board. You don’t need to explain to people why you’re still single and why you haven’t had children yet. Use that solo time to be specific about what you desire in a partner, and work on being the best version of yourself.

3d vector beach chair, yellow umbrella and ball, summer holiday, time to travel concept

Always take the vacation

getty//Getty Images

Melissa Magsaysay, journalist, author, beauty influencer, and co-founder of Duster, 45

I wish I’d known not to be so caught up in “relevancy.” I think so much of the stuff in my 30s was about relevance: having a byline and getting invited places because of certain things, being included in things, needing that kind of validation, being affected by the industry I work in. So, to put joy first, that felt so scary to me. But the reality is, if you’re constantly chasing relevancy, you’re never gonna catch it unless you redefine it. I wish I’d known just to put joy first, and your true happiness, and that’s when you’ll get off that relevancy hamster wheel.

What I Wish I’d Known in My 40s

I feel really good. I feel really dope. I’m winning out here. I don’t have a stylist, either. This skin? It’s all DIY.

I was in my 40s when the pandemic hit. So, I had a chance to sit. I had to. I had been freaking out about all of this stuff like “Does my vagina work like it’s supposed to?” But as the pandemic went on, I was just happy to have breath in my lungs and people to call.

I wish I’d known that friendships are supposed to change and morph. Some fade away altogether; it’s never too old to make a new connection. Anything that stays still and stagnant dies. The idea is to keep moving and evolving. In my 40s, I had been going through a divorce. I moved across the country, left the only city I ever loved [New York], and started all over again. In isolation, I had to learn to slow it down. I was in a lot of therapy. I allowed myself to get fat. I gained 50 pounds during the pandemic. It is not a bad thing. I have learned it’s okay to forget the story you made up about yourself.

Everything I made up. Like, “I have this gift. I’m a writer, but am I if I don’t have a serious credit?” I had been pushing so hard toward this goal, but then I was like, “But is this really what I want, or is it something I can do?” Some people call it starting over; I call it “a new story.” I had short natural hair when I came here. Now I’m like, “What if I got me a 22-inch weave?” Maybe this chapter, I’m a bad bitch. I get to make a new story.

For the first time, I am choosing to be who I am versus what I was “supposed” to be. I think there were a lot of people who tried to convince me. Sometimes it was my parents, my brother. Sometimes it was bosses, people who were supposedly mentoring me, and maybe they were all well meaning — they were trying to convince me, “Don’t be who you are. Don’t be so much you. You’re scary. Or intimidating. People are afraid of you.” Well, I used to joke all the time, “If you’re afraid of me, you ought to be.” Well, I’m now embracing that. I’m straight, no chaser. I’m my competence, my capability, my pursuit of excellence. That is intimidating if you settle for mediocrity. I’ll be 60 in September. It’s a little late to be coming into alignment with who you are.

What I would tell [the younger me] is that, even from the people who love you the most, take a real critical eye to what they are telling you. That signaling that you are not fitting the mold or who you are just isn’t quite right. There were just too many people trying to keep me from being me. And I am glad that I have seen the light; I’m glad that I am moving forward with what I want now.

Kathy Thomas, co-founder and co-president of outdoor-gear brand Salt + Snow, 50

Take care of yourself! Women are having children later and working longer and tend to put everyone else’s needs ahead of their own. Take time for yourself and for adult interactions — they will make you happier and actually allow you to take better care of the people who need you. Put your phone on airplane mode, and get outside! Gauge whether you need alone time on a hike, meditating, or doing yoga. If you need grown-up company, try golf, a dance class, or pickleball (although margaritas and nachos can also do the trick).

I learned how to surf when I was 42. That experience was largely the inspiration and catalyst for starting Salt + Snow at 50. Follow your passion, and learn something that is just for you! Surfing, guitar, skiing, rock climbing, ballroom dancing, tennis, knitting, hiking, yodeling! When you are in your 40s, you can have the confidence to risk embarrassment and enjoy and laugh at being a beginner but also feel the accomplishment of getting better at something. You may also discover a whole community you didn’t know existed. It may even prompt you to start a company! Surfing opened up a whole new world to me: the ocean, the people, the travel, my happy place.

As a mother and entrepreneur, the balance can be hard, especially later in life. When you start a family in your 30s, everyone tells you what to expect: newborn exhaustion, terrible twos, having to wrangle kids, and not getting enough time for yourself. My parents told me life started at 50, but they had kids earlier than I did. Having teenagers in today’s high-pressure, screen- and social media-driven world and then throwing taking care of elderly parents into the mix can bring on anxiety you never knew you had. It’s okay to feel overwhelmed. Appreciate the great moments, and take lots of deep breaths when things are tough. You are not alone.

Find activities you can do as a family. It’s surprising how much you learn together, and it’s an easy way to work through problems together. It’s also a great way to get them to talk about their lives without feeling singled out.

Figure out which people you can really be yourself with — the ones who make you laugh until you cry and with whom you can cry until you laugh. They are the ones with whom you will grow old (as well as drinking said margaritas).

happy black family having a creative time at home

Finding an activity you can do as a family can be the key to growing together.

skynesher//Getty Images

What I Wish I’d Known in My 50s

Caley Cantrell, retired advertising professor and author, 61

On the day I turned 50, I got up, made some coffee, and immediately posted on social, “Today, I turn 50” — or words to that effect. And then I started moving — had things to do. I felt good. I felt like me. Not “older” me. Not “nobody will care about me.” Not “I’m not relevant anymore” me. I was authentic before 50 and even more authentic after. I worry far less about myself.

I wish I had known, and been able to anticipate, the great release of crossing this social stigma bridge of age. That my voice would be more powerful — I could actually talk more softly because time was on my side. My age meant money in the experience bank. And that helping the next generation would be so much more fulfilling than fighting or fearing them.

People talk about turning 50 like it’s an expiration date on life’s milk carton. It’s not expiration; it’s liberation. You’ve earned the experience and knowledge to make smarter choices. You can lean into the friends and family who fuel you. You can choose to lean away from the wet blankets who bring you down. And hopefully — and maybe a little selfishly — you can put your time and energy into the things that make your heart sing. Fifty is not the finish line. It’s the new flame that warms what comes next.

Malcolm Venable is a Senior Staff Writer at Shondaland. Follow him on Twitter @malcolmvenable.

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