40 Pieces of Advice That Got Me to 40

Today I turn 40. Which, I’m happy to say, means now I officially know everything there is to know about life.

OK, maybe not. But I know a heckuva lot more than I did at 30, and definitely more than I did at 20. Hitting any milestone birthday naturally prompts some introspection, and lately I’ve been realizing how my point of view has been shaped by all of the people who’ve come in and out of my life over the years, and how what may seem like a throwaway conversation can have a lasting impact on someone.

So I decided to assemble this list of 40 pieces of advice that got me to today, in no particular order. Some of them are philosophical, some are practical–all are a reflection of the person giving them. And of course all come with the disclaimer that by no means do I follow these as well as I should. But it’s good to have goals–especially at my age. 

1) Charm is a verb. (Gavin de Becker, The Gift of Fear)

In college, I was obsessed with The Gift of Fear, a book about violence and personal safety by security expert Gavin de Becker. Oprah had him on multiple episodes, and his lessons still resonate with me since I first read The Gift of Fear nearly 20 years ago. (You can imagine my excitement when Amy Poehler mentioned her own obsession with this book in her memoir, Yes, Please.)

The book is not as alarmist as it sounds, but rather an empowering guide to which threats are real and which are not. One line that’s always stuck with me is this one about how women respond to men who are “charming.” De Becker’s point was women too often ignore their instincts in favor of assuming positive intent from a man who’s trying to lure them into danger, and that rather than being a character trait, “charming” is something that’s done to you.

But I’ve extrapolated this lesson into other parts of my life. I’ve become wary of the coworker you’ve known for five minutes who greets you–and everyone else–as “friend.” The woman who starts every, every conversation with a superficial compliment. The person who cheerfully reaches out to see how you’re doing, only when it’s followed by a favor to ask.  

Some people are kind, others are charming–and it’s essential to know the difference.

2) You’d worry a lot less about what people think about you if you realized how rarely they do. (Dr. Phil)

Make fun of Dr. Phil all you want, but the guy gives good advice. I saw him say this on Letterman once, and it’s a sentiment I’ve heard echoed by many mentors in my life. When I left Turner, I told a counselor, “I know everyone’s expecting me to do something amazing, and I’ll feel like a failure if I don’t.” She looked back and said, “But here’s the thing: nobody is thinking about you.”

At first I was hurt. Not only was I failing in life, but nobody was thinking about me! Then I realized how liberating it was to accept this fact. I didn’t have to worry about impressing anybody because nobody was waiting for me to impress them. It’s like when you’ve been in a bad relationship where you’ve been slowly changing who you are, and when you finally break up, in the middle of all the sadness you realize, Oh, I don’t have to pretend to be that person anymore.

If someone does want you to impress them or meet their expectations in order to earn their respect, that’s a reflection of them, not you.

3) Just as important as what the rules do say is what the rules don’t say. (Mrs. Dice)

In 7th and 8th grade, I participated in an event called Odyssey of the Mind. It was an extracurricular competition for nerds gifted students that comprised a variety of project-based events. Stuff like building remote-control robots or balsa wood structures that could withstand increasing amounts of weight.

The first year I participated, our team chose a category called “Cause and Effect,” which consisted of building a Rube Goldberg contraption that needed to start with the drop of a billiard ball, then perform a series of required actions: illuminate a light bulb, pour water from a larger container to a smaller one, reveal the words “Odyssey of the Mind,” etc.

Our coach was one of the English teachers, Mrs. Dice. At the start of each project, you received the list of rules for it. That was when Mrs. Dice advised us to look between the lines of the rules and spot the loopholes. She wasn’t encouraging us to cheat, but rather to think creatively, to look beyond limitations and be open-minded about what was possible within the project.

I’ve probably used this skill in my career more than any other. In almost any industry, the rules are changing. The people and companies finding the greatest success are the ones who think beyond the rules. Which makes me even more concerned about the sit-still, be-quiet, take-this-test philosophy that’s guiding public education now. I hope we’re lucky enough to find a school that encourages Archie to think bigger and look for what the rules don’t say.

4) Spending money and generosity are not the same thing.

I’ve come to appreciate this as I get older, both from a position of giving and receiving. I remember when my mom was going through her illness, an acquaintance of hers sent a very expensive gift basket to the house. But that was it. My mom never heard from her, never got a call to see how she was doing. On paper (specifically, the receipt), the gift was very generous. But in truth it was a shallow gesture that was more about the giver than the recipient, which is pretty much the opposite of generosity.

5) Pay yourself first. (Alan)

This is my husband’s mantra when it comes to our retirement savings (“It’s the one thing you can’t borrow money for”), and it also reminds me of a story I read in a Suze Orman column. A mother had written asking what to do about the new pair of shoes her teenage son wanted, something the family could not afford. Suze explained that what a child really needs are stress-free parents, and that going into debt for the sake of his temporary happiness would make things worse in the long run. That’s obviously easier said than done when it comes to kids, but I’ve taken the lesson to heart and tried to remember staying financially secure is the most rewarding gift we can give our family.

6) Overtip. (Mom)

My mom always valued anyone who valued work, so a few years ago she decided that instead of writing checks to charities, she was going to start overtipping for good service. “I’d rather give my money directly to people who are out here working,” she’d say. She wasn’t dropping C-notes or anything, but she figured what was only a few extra dollars to her meant more to someone for whom every dollar counts. So now when I can, I tend to round up as well.

7) If you hurt someone, all you can do is offer a sincere apology. If the other person refuses to accept it, that becomes their problem. (Miss Hanley, 9th grade World History teacher)

Miss Hanley is without a doubt the most memorable teacher I ever had. She was a former nun in her late 60s who dressed stylishly, always had her makeup on point, and lived alone with her Scottish terrier, Professor Scruffins. She had a poised, formal delivery punctuated by dramatic pauses. She didn’t so much teach her class as perform it.

Occasionally, she would pepper lessons with life advice or stories from her youth. (We all remember her description of a woman with a “Coke-bottle figure” who was “poured into that dress.”) For some reason, this tip about apologies has always stuck with me, I think because I’ve always tended to be a people pleaser and couldn’t stand the thought of someone being upset with me. In cases when someone else holds a grudge (or if I am), I remember this advice from Miss Hanley and give myself the freedom to move on.

8) You never know who you’re talking to. (Mom)

This dovetailed with Mom’s “be nice to everyone” advice, and they’re both rooted in a couple of ideas. One is empathy, that you never know what someone is going through that’s driving their words or actions, so take a moment to give them the benefit of the doubt. The other is more self-preserving, that you never know when you might meet this person again, who they might know, or whether they may be in a position to help (or hinder) you in the future.

9) She who gossips to you will be a gossip of you. (Mom)

Every woman knows this saying, and it has rarely stopped any of us from gossiping. The more accurate cliché is that refrigerator magnet that says “If you can’t say anything nice about anyone, come sit next to me.” But deep down, we all know gossiping is bad and can be extremely hurtful if you say the wrong thing to the wrong person. (See “You never know who you’re talking to.”) I know who my close friends are, the ones with whom gossip is just one component of our conversations, but I’ve become more cautious around women whose interest in friendship is based solely on sharing scoop.

10) When preparing a cup of coffee, put the cream and sugar in the cup first, then pour the coffee. This way, you don’t need a stirrer. (Brian)

My college friend Brian told me this trick once when I was getting coffee, and without being melodramatic, it was the single greatest piece of advice I have ever received.

11) Don’t live the life others expect of you. (The Top 5 Regrets of the Dying)

I revisit this article at least once a year, in the moments when I need a reminder to focus on what matters. This goes back to the idea of worrying what people think, and how in the end, none of those people will be there.

When my mom died, nobody came in with a scorecard and said, “Let’s tally it all up.” Nobody measured her achievements and how they compared to everyone else’s. What mattered was the people she loved, and who loved her. And it’s only by living a life true to yourself that you find those people, the ones who are real and genuine and unconditional and willing to be there when it’s your time.

12) I’d rather be a little crazy and have people remember me than to be “normal” and be forgotten. (Motivational speaker in high school)

Here’s the irony: I don’t remember this guy’s name. I don’t even remember the context for why they brought him in. But I do remember his speech and this moment from it. When he started talking, he was overly animated and boisterious in his presentation. We all thought he was crazy. Then he hit us with, “Now, I know you all think I’m crazy, but….”

I’ve taken this advice to remind myself it’s OK to stand out, to own your quirks, to speak up with the question everyone else is thinking but not asking. It can be risky to be different, but it’s almost always preferable to blending in.

13) Life is what happens to you while you’re busy making other plans. (John Lennon)

Mom quoted this all the time, especially following her diagnosis. A classic reminder that we’re ultimately not in control, and to enjoy the moment in front of you.

14) After you graduate high school, nobody cares what your class rank was.

I was valedictorian of my high school class. My husband was valedictorian of his. The last time this was relevant information? The day we each graduated high school. While we both certainly would be proud to see Archie reach this accomplishment, by no means are we going to pressure him toward it.

We respect education immensely, but we both feel there’s too much focus on academic achievement as an indicator of self-worth for today’s kids. When in truth, the majority of our jobs today are centered on navigating relationships, thinking creatively, solving problems, and embracing change. We would rather have Archie be a C student who is confident, compassionate, curious and kind than an A student who’s myopically focused on his grades.

15) Fail by daring greatly. (Brene Brown)

I’ve written before about the role Brene Brown’s Daring Greatly has played in the last couple of years of my life. The overall point is that failure is inevitable, and nobody is perfect. Don’t ensure failure by never taking a risk. Fail by daring greatly.

16) People are usually dumb before they’re malicious. (A.J. Jacobs)

This was in an advice column I read online in which someone presented a detailed scenario of how they felt another couple had misled him and his wife on an offer to buy dinner. Apparently, they had said, “We want to take you to dinner,” then when the check came they split the bill. There was parsing of every word and questions about whether “take you to dinner” meant they were picking up the check or not. The writer said he was ready to cut off the friendship because of how offended they were by this about-face.

Jacobs solicited reader answers, and he highlighted this one as “what should be the new Golden Rule.” I think women especially have a tendency to do this, where we take one comment or action by another person and spiral it into some vast conspiracy to ruin our lives. But chances are, they just had a moment of dumbness, the same way we all do.

17) Be ruthless with your prose. (John Kupetz)

If I have any level of writing ability, it’s because of John Kupetz. He was my professor for Basic Writing, the first journalism class you took at Medill back then. The course’s reputation preceded it, Kupetz’s even more so. No detail slipped by him. He enforced the infamous “Medill F” for articles that included a single factual error. He didn’t suffer fools gladly. When someone in our class said something he found annoying, he’d point at them, grin maniacally and say, “You’re the reason I drink in my closet at night.”

But as the story usually goes, he was my favorite professor at Northwestern. This blog post not withstanding, he taught us to make every word count. Even as I write this, I’m hearing his voice in my head, picturing his green pen making swirling edits. (“I use green because it’s the color of hope.”) I apply something Kupetz taught me every single day, and I’m grateful that even now, more than 20 years later, he’s still making me a better writer.

18) People who are familiar pose a bigger threat than strangers. (Gavin de Becker, The Gift of Fear)

This was another revelation for me when I read The Gift of Fear, and it’s a lesson we’re going to emphasize with Archie. De Becker talks about the fallacy of telling kids “Don’t talk to strangers,” because a) they see us talk to strangers every day, b) someday they may need a stranger’s help, and c) they’re more likely to get hurt by someone who is not a stranger.

Instead, we want to teach Archie to trust his instincts around *all* people, and assure him we are his allies against *anyone* who makes him uncomfortable–even if that anyone is a friend, family member, teacher or coach. People who do bad things are not “monsters.” They’re ordinary people integrated into our everyday lives, and it’s only by accepting that reality that we can be attuned to avoiding the threat they pose.

19) You are not your job.

This was my biggest takeaway from leaving Turner. As invested as I am in doing good work, I’ll never again let it define my identity.

20) Stress makes your brain physically incapable of creativity. (Time Warner leadership class)

A few years ago, I went to New York for a women’s leadership seminar at Time Warner. Initially, I rolled my eyes at what I imagined would be the same banal, rah-rah, girl power spiel I’d heard many times before. But instead, I came away with several inspiring and practical insights, the most striking of which was this one.

I had always equated stress with work, and work with achievement. If I wasn’t coming up with good ideas, it was because I wasn’t working hard enough. This flipped the switch. When your brain is in stress mode, it prepares for fight or flight by shutting down non-essential functions–like empathy, logic and creativity. I was caught in a vicious cycle where I was stressed about not doing good work, and that stress was literally depriving me of the exact skills I needed to do my job.

Stress isn’t avoidable, but I’ve learned it’s not something to be embraced as a badge of productivity. If anything, it’s a reflection of the opposite.

21) When you face a crisis–large or small–look at it through the 20-Year Lens.

This is also inspired by the themes of “Regrets of the Dying,” the idea that nobody on their deathbed says, “I wish I’d spent more time at the office.” In so many moments now, I think, “How will I view this moment 20 years from now? What will matter?”

I remember one afternoon the SVP of our department was heading out of the office early. We were in the elevator together and he explained he was leaving to meet his wife for their 25th anniversary dinner. There had actually been a last-minute executive meeting that came up, and his boss was not happy he was leaving. But he said he’d rather deal with an angry boss than an angry wife.

Also, in 20 years, his boss won’t remember what meeting was even about, let alone that this guy missed it. But his wife sure would remember if he missed an anniversary for work.

22) If you can afford the difference between good seats and bad seats at a show, pay for the good seats. (Dad)

You’ll eventually forget the money, but you would always remember if you watched the entire show from behind a pole.

23) People will forget what you said, people will forget what you did, but people will never forget how you made them feel. (Maya Angelou)

This lesson came into stark focus after I left Turner. I realized when I looked back at my years there and the people I worked with, I didn’t remember specific projects or PowerPoint presentations, but I did remember who I liked working with and who I didn’t. I remembered whose smiles were sincere and whose were forced. I remembered who didn’t take themselves too seriously and who entered a room ego first. And in the spirit of the 20-Year Lens, guess which people matter more to me now?

24) You have to set your own boundaries or no one else will. (Counselor)

I had a counselor tell me this when I was talking about how stressed I felt by work, often staying at the office past 7 p.m. because I had so much work to do, and if I didn’t put in the extra time, the work wouldn’t get done right. That’s when she explained that there would always be too much work, that the to-do list would never be complete, and it was up to me to draw the line each day.

25) Sleep begets sleep. (Marc Weissbluth, M.D., Healthy Sleep Habits, Happy Child)

The best advice we read when we had Archie. My friend Anna gave us this book and said it saved their lives when they had their first child. And while everyone has their own baby advice book that works for them, this was the one that worked for us.

The logic behind “sleep begets sleep” is that a tired baby does not sleep better; in fact, he sleeps worse. This is because he gets so tired that he becomes upset, making it harder to get him to sleep. By establishing and maintaining a regular sleep schedule–and putting him down before he’s tired–you’re essentially teaching your child how to sleep.

This becomes especially beneficial in the middle of the night when your 6-month-old wakes up and starts crying, but after a few moments is able to calm himself back down to sleep. Or even better–doesn’t wake up at all. Those are the moments Alan will turn to me, raise the roof, and say, “SBS, baby!”

26) Magazines, TV and movies are not real.

This seems obvious, but for a long time I subconsciously thought my kitchen was supposed to look like Diane Keaton’s in “Something’s Gotta Give.” I read Real Simple like it was an instruction manual. The first time my husband and I had a fight, I assumed it meant we weren’t soulmates.

My lifelong pop culture diet had left me with unrealistic expectations of what life was supposed to be like, and when actual life presented itself in all its mundane glory, I took it as a sign I’d failed somehow. Now I realize these are just images created by regular people–editors, screenwriters and producers–who all leave the studio each night and go home to their real lives. As much as I love media, I now view it through a more discerning lens.

27) Have friends over even if your house is a mess. (Erma Bombeck)

Several years ago, I bought a book of Erma Bombeck essays, and one that stood out was “If I Had My Life to Live Over Again.” After Bombeck learned she had terminal cancer, she put together a list of her regrets. They’re all poignant, but the one that stuck with me was: “I would have invited friends over to dinner even if the carpet was stained and the couch was faded.”

Just like the to-do list will never be done, the house will never look like a magazine cover. Here again the 20-year rule applies: If you have friends over and you all talk and laugh and have a great time, chances are good that 20 years from now, they’re not going to say, “That was such a fun night. Too bad it was ruined by that pile of dishes in the sink.”

28) The older you get, the more you need the people who knew you when you were young. (Mary Schmich)

This is from that “Wear Sunscreen” essay that erroneously got forwarded as a commencement speech by Kurt Vonnegut. In truth, it was written by Chicago Tribune columnist Mary Schmich as her own version of what she’d tell a class of graduating seniors. This line has always stayed top of mind for me, and it has taken on new resonance as I get older.

29) Gift giving is not a transaction. (Ginger)

Ginger was one of my first friends in Atlanta, and to this day she’s still one of my closest. She worked as the office manager at Cartoon Network Online when I first started at Turner, and one Christmas she surprised me with a present. I apologized for not having a gift for her, and she told me, “People don’t give gifts to get something in return. The joy they get is seeing the person’s happiness when they open it. So give them that joy by genuinely accepting the gift they’ve given you.” Well, you know what else is a gift? THE WISDOM OF GINGER.

30) Eat the frog first. (Harvard Business Review)

When I wasn’t working, I spent a lot of my time reading articles about the best way to work. This was a metaphor for tackling the hardest task of your day first. You’re at your freshest, and you’ll feel more productive the rest of the day knowing it’s smooth sailing now that you have that beast off your plate. You may even have time to think of more mixed metaphors!

31) Just because someone tosses you a ball doesn’t mean you have to catch it. (Molly)

Molly was another former colleague at Cartoon, and this is one of my favorite things she ever said. It can have several applications, whether it’s not letting yourself get baited into an argument or saying no to the request to help make Spirit Day decorations for your son’s daycare. Don’t let someone else add stress to your life out of obligation or people pleasing. Chances are, they’re not going to give it a second thought and will move on to the next sucker willing to catch the ball.

32) Nobody can make you feel inferior without your consent. (Eleanor Roosevelt, as relayed via Mom)

My mom used to quote this to me when I was getting made fun of or felt excluded at school. It’s hard for a child to understand this, since you still don’t know who you are at that age. Part of the joy of turning 40 for me is the confidence and comfort I have in my own skin. Now I can appreciate that if someone is going out of their way to make you feel worse about yourself, they’re the one with the problem, not you.

33) When parallel parking, start straightening out a second sooner than you think you should. (Dad)

I’m just gonna come right out and say it: I’m awesome at parallel parking. And it’s because of this life-changing tip from my dad. If you wait too long to start straightening out, that’s how you end up angled into the curb. If you’re nervous you’re going to hit the car in front of you, remember that you’re also moving backwards as you straighten, so you’re moving away from that other car. The only things that are going to collide are you and some mad parallel parking skills.

34) Turn the water off when you’re brushing your teeth.

The environmental movement of the ‘70s led to a lot of film strips watched by grade school kids in the '80s, and I remember having this message hammered into us over and over. To this day, I feel guilty if I leave the water running, like I’m literally draining our precious oceans into my sink.

35) Three things in life are important: The first is to be kind. The second is to be kind. And the third is to be kind. (Henry James, by way of Mom)

My mom loved this quotation so much she gave my brother and me each framed prints of it. It’s important to note there’s a difference between being kind and being nice. To me, being nice is an action, something you do at certain times. Being kind is deeper. It’s a quality, something you are. And sometimes the kind thing to do is not always the nice thing.

36) Living in the past is depression, living in the future is anxiety, living in the present in peace.

I saw this somewhere on the Internet. And unlike most things on the Internet, it’s 100% true.

37) Stop saying “sorry” so much. (Rebecca)

When I started my internship at Turner, my first rotation was through TNT Marketing, where my point of contact was a woman named Rebecca. Every time I had a question, I would walk to her cube and feel like I was interrupting what she was doing. So I’d start with “Sorry, but I had a question about…”

One day, she cut me off. “You have to stop saying 'sorry’!” she said with an exasperated smile. “First of all,” she explained, “you have a right to be here. By starting with 'sorry’ you’re implying that you don’t.” She went on. “Second, you diminish the meaning of that word if you use it all the time. Save it for when you really need it.”

There have still been plenty of times in my life when I really needed “sorry,” and I know I still use it in times when I really don’t. Either way, I still hear Rebecca’s voice in my head, and cringe when I hear other women (and it’s usually women) starting their sentences with it.

38) Yes, and… (Improv)

This is the core philosophy of improv comedy, that when performing, you accept what is given to you, then build on it. The idea is to embrace spontaneity and not bring a preconceived notion to the scene. So if you’re imagining you’re plumbers, and your partner says, “I can’t believe we’re delivering our 1,000th baby,” then you’re now delivering a baby. You don’t argue back and say “No, we’re fixing a leak!” unless you want to grind the scene to a halt and frustrate everyone in the room.

The same philosophy holds true in any act of creation, whether you’re brainstorming ideas at work, building a life with your spouse, or raising a child. The very nature of life is unpredictable, and the harder you try to keep control, the more miserable you and everyone around you will be. Keep the scene moving. Accept what is given and choose to build on it together. Chances are you’ll end up somewhere much more entertaining than you ever could have planned.

39) Be open to connecting with other people. (Dad)

When I was growing up, my mom was my primary social mentor, guiding me on the idiosyncrasies of female friendships. She was the one I talked to when I made a new friend, or when another girl had hurt my feelings.

So it surprised me when, on the night before I left for college, my dad came up to my room while I was packing. He sat me down and said, “I want to tell you something. When you get to school, I want you to be open to people. Don’t be afraid people are going to let you down and let it keep you from making friends.”

He saw a truth that I hadn’t yet, that as much as my mom loved her close friends, she could be very unforgiving if she felt someone had disappointed her. My dad wondered if she had been burned by a friendship when she was younger, and if that’s why she’d become so cynical about trusting new friends. Either way, he didn’t want that attitude to carry over to me.

I was still insecure and anxious during most of my freshman year, but I made some of my best lifelong friends in my dorm that first semester. Since then, I’ve learned humans are wired for connection, and that we’re all bound to let each other down from time to time. The friends who matter are worth forgiving, and will forgive you.

40) Aging is a privilege. (Mom)

My mom was a daily reader of the obits. She was fascinated by people’s stories, the lives they led, and would remark that aging is a privilege. When we were going through her things after she died, we found a list she had jotted down on a small piece of paper. It was titled “The Blessings of Cancer,” and among them was “Makes your goal a chance to grow old.”

Once again, you were right, Mom. There are a lot of people who never even made it to 40. I promise to follow your lead and never take any day for granted, to embrace life’s changes as a gift, and to appreciate the privilege of aging for as long as I’m lucky enough to have it.