When one hits a milestone birthday, he or she might take a moment to pause, reflect and write down the lessons of the decade prior. I didn’t do that when I turned 30 last year. I guess I wanted to see the entire year through before I made any grand pronouncements about what I’d learned in my twenties. I’m glad I did. Age 30 turned out to mark a sizable shift in my life. It brought a generous flood of new opportunities, both personal and professional, all of which culminated in a year of significant growth. I’m turning 31 this month. Given the space from my twenties, I think I have a (slightly?) more educated perspective than on my last birthday. Or maybe I’m just, y’know… older.
These are the most important lessons I walked away with:
1. You will only ever have one first love. This is powerful because you haven’t been wounded yet; you are raw and lacking cynicism, so you can love someone from a place of real purity. I was given the gift of falling very deeply in love at 19 years old. I was lucky that it was a good love, with a kind and wonderful man who was my best friend. When we broke up right before I turned 25, I was devastated. I put on a tough facade, but inside, I selfishly did not want to let him go. Which brings me to my next lesson…
2. If you love someone, let them go. I know, what a cliché. In my case, that meant encouraging the person I loved most to go his own way without me. When I realized he never would unless I left him, I made the heart-ripping decision. But he has gone on to have incredible success. I would never have the admiration for him I now do had I kept him tethered to me. It would be resentment residing in admiration’s place — resentment for holding each other back professionally and resentment about a marriage I was not ready for. Instead, I can genuinely say I will always love him and that I am so beyond proud of him to this day.
3. The strongest people are the most vulnerable. I can’t emphasize this one enough. I used to think cockiness was a sign of strength in the men I dated. As I grew older, I realized that cockiness is designed by weak folks to distract you from how much they don't like themselves. It is the truly confident who know and like themselves enough to show themselves to me, admit that they want to build their life with a partner, and are okay getting scary close despite their imperfections and mine… those are the men I want in my life. It takes me awhile to trust someone, but once my guard is down, I really work to be vulnerable in the same way.
4. Looks *really* aren’t everything. Speaking of dating, when your Grandma tells you to skip over the beefcakes and head straight for the nerds, for heaven’s sake, listen to her! All the guys I dated solely for their looks in my twenties have since lost their hair, or gained weight, or gone to rehab, or insert not-so-sexy thing here. Whatever. You get it. Not to say physical chemistry isn’t important, but these days when someone asks me what my type is, I genuinely mean it when I say I want someone who is smart that makes me laugh. Looks rank way, way further down. And if he’s brilliant, he's already Brad Pitt in my eyes.
5. Share your needs up front. Whether those needs are social, emotional, sexual or otherwise, the things you deny yourself at the beginning of a relationship because you fear rejection are ultimately the things you’ll most resent your partner for denying you down the road. If you like weird stuff in bed and he’s strictly missionary, if you hate being cooped up in the house all the time and he’s a total couch potato, if you hate PDA and he loves to have his arm around you all the time… guess what? It’ll all pile up and start to piss you off. A lot. Just get those talks out of the way early on. If your needs happen to be his deal-breakers, congrats, you both just saved yourself a lot of time and turmoil.
6. Expect new people to earn their place in your life. I was in a pattern a few years back where I prioritized dating over my friends. Guess what? My friendships suffered. It dawned on me when a group of girlfriends were putting me back together after a particularly rocky breakup that I’d never made this guy earn the top spot in my life. I just gave it to him, no questions asked, head and shoulders above all the people who were there long before him. These days, I choose my friends and family over a new romantic interest. I will work him into my schedule after them, and it is only when I feel good about him that I start shuffling him up the ladder.
7. We all define safety differently, but we all want to feel safe. Our sense of safety governs our partnership decisions. I know girls who have plenty of money who don’t give a hoot if you’re rich, they just care if you tell the truth. Emotional security makes them feel safe. I also know plenty of others that won’t look at you twice until they see what car you’re driving and watch you’re wearing. Financial security makes them feel safe. Still others do not feel safe with anyone who isn’t a Christian or from a similar background. That’s religious and cultural safety. For me, it’s intellectual and social safety. A person is not needy, a gold digger, sanctimonious, shallow or a zealot because they define safety differently than you do. Just be honest about your definition of safety in love, and seek it. I promise, there is someone out there who will make you feel safe.
8. There is nothing wrong with being single — in fact, it can be pretty awesome. If you know and like yourself, being single is no big deal. I have had a few boyfriends in the last few years, but if it isn’t a match, I don’t worry about ending it, because I’m not afraid of being by myself. I enjoy the stretches of time I get where my only responsibilities are myself and my dog. I know one day soon that won’t be the case, so it’s pretty fun to be a little selfish right now and drive the car that I want, travel when I feel like it, and not have to really answer to anyone. If you find yourself jumping from one relationship right into the another, I really encourage you to find a time in your life to be single and get to know the you that you are when you’re not one-half of a couple. You’ll be so glad you did.
9. Say no. Say no a LOT. The biggest mistake I made early on in my career was trying to please everyone. I said ‘yes’ to everything. Because of that, I missed deadlines, pissed people off and the quality of my work suffered. These days, I say ‘no’ to 80% of the things that are asked of me. This is not to be rude by any means, it is simply to protect my time so that I can focus on making the projects I choose to do truly great. Yes, this means you’ll turn things down that absolutely kill you to say 'no' to. Yes, you’ll probably still bite off more than you can chew sometimes and sometimes say 'Yes' to things you later wish you’d declined. That's okay. Just remember, no matter how much somebody guilts you, if your gut is telling you this isn’t the right project, relationship, job, media opportunity etc. for you, try to remember to listen. And then, say no.
10. Learn to delegate and collaborate — and value the folks you do it with. Like every human being on the planet, I am awesome at some things, and I totally suck at others. I used to try to do the things I suck at myself (basically anything having to do with numbers, for example. Thanks, dyslexia!) That didn’t work. Then I tried having other people do those things… for cheap. That didn’t work either. Finally, I learned that the people who help fill in the gaps for you are worth every single penny. In one way or the other, we are all being delegated to, and don’t you want to be paid what you’re worth? Which brings me to my next point…
11. Establish the value of your time, stick to it, and grow it. When I was 22, I let someone pay me five hundred dollars for a complete logo suite (!!), killed myself designing something I thought they’d like based on poor art direction, gave them unlimited revisions, and then cried myself to sleep when they screamed at me that they hated everything and that I wasn’t trying hard enough (okay, so that was just one memorably bad client experience out of many great ones, but I digress)!! I wish I could reach back in time and shake 22 year old Jess straight. But I learned a lot of good lessons there. One, it taught me how to sniff out a problem client. I can smell unrealistic expectations from a mile away these days, and I manage the hell out of them, or simply pass on the job. Two, I know how to ask the right questions to get the direction I need. Not everyone is an excellent communicator, and not everyone knows what they want. Third and most importantly, it was the first lesson I received in valuing my own time. Had I been armed with a sense for their wild expectations and an understanding for coaching good direction, I would have known how much to charge the client based on how much time I knew they would gobble up. And it would have been a hell of a lot more than five hundred bucks.
12. Lead with outrageous care. Okay, okay, I totally stole that line from my (very brilliant) friend Brett Trapp. But for real, guys. It is so true. If you are in a leadership position, you can lead by tyranny or you can lead with care. It is a simple choice to be interested in the people who work for, with and around you. If you terrorize, undermine and belittle them, they won't stay. I don't need to tell you that lack of retention is an expensive problem and bad reputation to have as an employer. Am I mushy-gushy touchy-feely? No! That isn’t my personality or my leadership style, but that doesn't mean I'm not deeply invested. I’m a very straightforward person. The people who work on my team (past or present) know where they stand at all times, that I am personally committed to the growth of every one of their careers, and that I will remain very loyal to them.
13. Work really, really stupid hard in your twenties and thirties. I know there will come a reward phase of my life later on if I grind while I still have the energy and freedom.
On the negative stuff…
14. Difficult as it may be, just ignore the haters. I was thinking back on my time at Shops Around Lenox the other day and all the amazing work I got to do at such a young age. My boss at the time was a real forward-thinker who approached me out of the blue, created the Creative Director role for me, and wanted me to leverage my influence to position myself as a visible face of the brand. The work I did there is still some of my best. In many ways, I am so grateful for that opportunity. It really helped set me up for the future. I remember being very conflicted about making the decision to leave, I'd just been promoted and given an office! But I really wanted to focus on my writing and growing The Love List at that time. Soon after I left, some nasty rumors emerged that I’d been fired for being an “egomaniac”. That really hurt me. It was just SUCH a blatant lie. Another thing I heard about myself was that I changed my last name as a publicity stunt, when in reality it was part of a deeply personal decision to take my Mother’s last name and distance myself from my birth Father (more on that in bullet number 13.) Even though I knew the source of the nastiness (and this was a really aggressive takedown/bully campaign for awhile), I resolved to not engage. I just had to silently thank ‘em for making me feel so relevant! You’re nobody until you’re talked about, right? All jokes aside, when you have a job with any level of visibility, you subject yourself to public opinion, and not all of it is nice. You just have to resolve to stop reading the (literal and figurative) comment section! For every one hateful email I got, I got sixty that were encouraging, positive and kind. It is so easy to focus on that one negative thing rather than the numerous positives, but you have to choose the good stuff. In the age of the internet, achieving any real success comes hand-in-hand with trolls, that’s just life. Just twirl on ‘em and keep being you. To paraphrase my boy Justin Timberlake, their voices will fade. You wont.
15. On that note, try not to participate in gossip. Otherwise, you’re just another troll. Gossip is a waste of energy, and it always eventually claps back to the source.
16. …And stop worrying so much about what other people think! Skip this bullet if foul language offends you. You’ve been warned… All my friends all laugh at me because I truly give no fucks. They even made a plaque for my desk at work that says “Zero Fucks Given”. I’ve kind of made it my thing. I used to spend a lot of time overcompensating for my insecurities, trying to impress people and fretting over their opinions. At some point, I just said “fuck it” and stopped making calls based on what people would think about me. I have never made a better decision for myself. I encourage you to stop giving so many fucks as well. As they say, opinions are like assholes, everyone’s got one. Decide whose opinion matters to you, take their counsel to heart, honor them, give them your time …and then put everyone else in the “fuck it” bucket. If you don’t, you will wake up one day literally drowning in assholes with absolutely no memory of who you really are. And then you’ll just be fucked.
17. Accept the fact that sometimes, you’re going to get screwed over. Sometimes, boyfriends are going to lie to you to get what they want. Sometimes, friends will stab you in the back to get a leg up. People close to you will die young or tragically. Maybe you’ll get in a car accident. Maybe you’ll pay fifteen bucks to see a movie in the theater that totally sucks. Maybe your favorite band will break up. Maybe someone will call you ugly. “It’s like ten thousand spoons when all you need is a knife…” Shit happens. Shake it off. Hug it out. Call your Mom. But then get on with your life. You’re a freakin’ grownup, not a victim.
18. …But also trust that sometimes, you’re going to get lucky. Out of the blue two years ago, a mentor came into my life who has taught and continues to teach me so much. I’ve sat down at my computer multiple times to try to put into words how much she means to me, and I am so overwhelmed with gratitude that my brain locks up. I randomly met my best friend because he was the only guy in my college boyfriend’s fraternity house who had any means of making coffee. And the other day, I found twenty bucks at the bottom of my handbag! See? Luck!
19. Take chances on people. Sometimes, you have the opportunity to be close to someone with a dodgy reputation, date a guy who might be a player, let a family member back into your life who hurt you, etc. I admit it is a huge risk to let people like that in or back into your life, but a risk with huge payoffs if it works out. It may bite you in the ass to show empathy a time or two, but most of the time, at least in my experience, it won’t. Most people genuinely want to be good and do right by people. Sometimes, you just have to give them a second pass at it.
20. …But don’t be afraid to remove someone from your life, either. Sorry Biebs, sometimes, it is just too late to say sorry. I’ve had a handful of friends take advantage of me when I took a chance on them, whether it was recommending them professionally or by simply making the decision to be close to them despite being warned otherwise. If a person apologizes, I usually let them back in, but three strikes, you’re out. Family is more complicated. I haven’t seen or spoken to my Dad in more than ten years. I feel that hole in my heart with every breath I draw. I live with that abandonment and fear and sadness every day. I deeply miss so many things about him, and I like to I think he’d be proud of me, because I turned out to be exactly who he wanted me to be. But my Dad is a mentally ill, self-medicating addict. He is also very brilliant, sophisticated and handsome. His intelligence makes him a great liar, which helps him hide his addiction, and his good looks and wit make people tend to look the other way about his bipolar behavior. He is very deeply cruel, verbally abusive and mentally manipulative as a result of that combination. As I mentioned earlier, I even went so far as to take my Stepfather’s last name when my Mom remarried to distance myself from him. So despite the piece of myself I feel is missing, I know that having him in my life is not a healthy option. Not one day goes by where that resolve gets easier to maintain, but I stick to my guns, because missing someone is sometimes better than taking them back.
21. If you want to get to know someone, have them over for dinner. Cook, break bread, drink wine into the wee hours, break out the Cards Against Humanity. Open your home, no matter how humble, to other people. Make something for them or make it together. Dinner parties are the literal marrow of life. Have more of ‘em.
22. Make opposite-sex friends when you’re young... and keep ‘em. As you get older, new male/female friendships are a little touchier. If you’re both single, people wonder why you’re not dating. If one or both of you is married, it creates potential drama with the spouse. Most of my close male friends are people from high school, college and my early/mid twenties. (And a couple of exes.) I have never been the girliest of girls, so they provide great balance in my life! There is nothing like a male perspective sometimes. Those friendships mean the world to me. And as we get older, most of them have married awesome people who have also become my friends.
23. Your girl friends are sacred. I may not be a girlie girl, but I am most definitely a girl’s girl. I love my fellow woman. I think we are an entirely awesome gender, and both my girl friends and Beyoncé continue to drive that point home on the daily. Work hard to be a good girl friend. Be loyal, be supportive, do right by them, show up for them. Don't talk shit. Don't isolate people. Quash jealousy, that’s your own insecurity at work. Oh, and girl code is a thing. Respect it.
24. You can’t make new old friends. Is there anything better than talking with someone who you literally met on the playground? I treasure my hometown and college friends. If you have a friend who you can pick up the phone and talk to about some boy you had a crush on in the 8th grade with zero back story required, you did something right in your life.
25. Recognize for your own patterns. What do your closest friends have in common? Many of the people I love most are ambitious, relationship-driven, put together, and great at conversation. More of those people, please! I also have a tendency to date tall, dark-headed, fast-talking jerks. So maybe I should try not to do that anymore? I'm not saying I'm in a perfect position to give advice, but try to identify and get ahead of your own patterns until it becomes a sixth sense. I have found so many wonderful friendships that way. In the opposite vein, I’ve also dodged a few assholes.
On life in general…
26. Find your voice. What does that mean? It means standing up for yourself. It means speaking up on behalf of someone else whose voice is being drowned out. It means learning how to defend your opinions in a respectful, articulate way. It means figuring out what you have to say, and then actually saying and owning it.
27. You can (almost) always walk away. From a job. From a relationship. From nearly anything that is going badly or making you miserable. In most common circumstances, you are participating at will. Difficult as it may seem to uproot yourself, muster up the bravery to be an advocate for your own well-being.
28. Forgive yourself. I have done some next-level stupid stuff in my day. Years 25/26 were particularly devoid of good decision-making, so much so that I now lovingly refer to them as my “tailspin years.” What did that entail, you ask? Let’s just say breaking up after five years with the same person sends you into a bit of an identity crisis. I was in so much pain. I didn’t know how to deal with that pain at all. I genuinely cannot think of a single good decision I made in those years. I went on a month-long road trip with a complete stranger, I drank a little too much, slept with men I shouldn’t have, put myself in a lot of dangerous situations, made terrible financial decisions, talked tons of trash, told lies to cover up the trash I talked, fell into a crowd of kids who really warped my values, lost lifelong friends… I mean, the list goes on. Maybe it’s why I try to be so forgiving of others, because I remember how often the people who love me had to forgive me back then. I would be so lost had they not forgiven me, had I not had them to lean on. I would have never come back from the tailspin! Eventually, I learned how to forgive myself for those things. Only then was I able to finally stand on my own two feet.
29. Start something that is yours. I started The Love List when I was 20. I kept at it for eleven years. It’s mine, I made it, and I’m proud of it. It has opened more doors for me than it ever closed. It helped me find my voice, meet my heroes, embrace my niche, gain influence… it was a good decision. I encourage you to start something at some point in your life, too. That may or may not be a business, it may never make a dollar or it may make you rich, I have no idea. All I know is that it will make you feel happy, proud and validated in a way nothing else can. Even if it ultimately fails or ends, who cares? The point is that you did it.
30. Get nerdy about something. For me, that is oysters, Game of Thrones and grammar.
31. Reflect. Pause every once in awhile and audit your week, your year, your last decade on the planet, your life. Do it on paper, do it in conversation, do it with your therapist, do it in bits and pieces or do it all at once, but do it.