Over the past few years, around my birthday, I’ve set a tradition of reflecting on the previous year and writing helpful lessons from life/work.
This year, just before I made another lap around the sun, I added a new constraint by setting a timer and not editing or touching the content once the timer finished.
So here are thirty-one lessons written in thirty-one minutes from my last hours of being thirty-one:
31) Friends are more important than money.
30) Money is just a resource. It is renewable.
29) Time is not renewable.
28) If something temporal is stressing you out, cut it. Life is too short.
27) You can skimp on space only for so long. Make your home and office as comfortable and inspiring as possible.
26) Inspiration is like food. You need it to be full. Consume it in all its forms. And often.
25) A few nice things are more valuable than a lot of not-so-well-made things.
24) No one cares about you and your work as much as you do. This is liberating.
23) People do care about how much care you show. Listen. Respond. And show up.
22) Life is going to take shots at you. From all angles. Keep a thick skin and a soft heart.
21) The way to keep your skin thick is to only have a few close friends who know all aspects of your life. Just a few.
20) The way you keep a soft heart is by spending time with a lot of different people and placing yourself in their shoes as you listen to and work with them.
19) Try to make important functions of life automatic. Auto-withdraw money into your savings accounts. Go to sleep at the same time every night. Wear as simple of clothing as possible – consistently. Routines make space for the important things.
18) Spend a lot of time with your family. Especially your parents. They won’t be around forever.
17) Buy the nicer versions of the things between you and the ground (ie: shoes, mattresses, and tires).
16) Don’t be afraid of saying, “I don’t know.” But try to follow it with a helpful question or a possible solution.
15) Even if you don’t think you’re a writer, write. Getting things on paper is how you learn how to decipher between the shitty thoughts and the truth.
14) If you think something won’t work, test it in the quickest way possible. If it’s not working, don’t force it. Let it go. If it’s still on your mind months later, revisit it. Time away from things creates fresh perspective.
13) Take at least one day a week away from screens. If you don’t know why, you should probably take several days away from a screen. Because chances are, you’re losing touch with what matters.
12) Find one or two things you enjoy doing that has nothing to do with productivity. Get lost in them.
11) The world is messy and kinda scary. But you don’t have to be that way. You can control the way you engage it.
10) Move forward despite your fears and you’ll inspire others to do the same.
9) The best form of revenge is to continue.
8) The best way to honor those who’ve gone before you, is to continue with integrity.
7) You can’t do everything well. Ask for help. The sooner you ask, the less desperate you’ll be and the more others can truly be there for you.
6) When you travel, use packing cubes. They make traveling a cinch.
5) Plants are the best roommates.
4) Just because a leader is loud and brash does not mean they are good and right. Learn to lead with soul and conviction. You’ll know you’re doing this well when those whom you lead begin to hold you to your word and even add their own soul and conviction.
3) Keep good friends close for a long time. They get better with age.
2) There is no perfect formula for dealing with loss. But nature is part of every version of that formula.
1) If you’re unsure of what to write, set a timer and a theme. Then write until that timer goes off.
No matter how hard you try, nothing will be perfect.
I know that may sound pessimistic; but the truth is, most things will go differently than you expected.
The new thing you purchased will eventually break, get damaged, or become obsolete.
The idea you have will take more work than you envisioned and yield different results than you anticipated.
The thing you’re building won’t be as smooth or as polished as you had hoped.
Someone you greatly admired will make a mistake.
No amount of money or resources can change these scenarios.
But here’s the thing: It’s ok.
Perfection is an endless pursuit that leads to heartache, fatigue, and disappointment. If you’re feeling frustrated, redirect your energy from perfection to excellence.
Excellence is the act of practice multiplied by consistency and reflection.
It’s striving to do your best each day and in each moment – paying attention to the times when things went wrong and adjusting to make them better.
It’s hard to remember this in the moment. We are inundated with short snippets of lives that seem perfect. So we build grand ideas of the perfect partner, the perfect home, the right amount of well-curated possessions, the overnight-business success, and just enough unique experiences to seem cultured and adventurous.
Those pursuits of perfection may seem great on the surface, but they won’t leave you satisfied.
Find simple healthy rhythms and keep to them.
Push through the challenges by pausing to look back.
Lean on your community for advice and support.
Redirect as needed.
You’ll get to the end more healthy than when you began.
You won’t be perfect.
No one needs you to be.
But you can be excellent.
PS: Thanks for all of the support last week. We made it to the very last round, but didn’t receive the grant (quick story here). Thanks for your responses and support!
Ten days ago, I submitted a video and a few essay answers for a grant opportunity for Experience Institute’s work with college students.
A few days later, I found out we were a finalist for the mid-tier level, roughly $180,000. The final step is to pitch in front of a group of judges and a live audience.
After a crazy week of preparation on top of an already full schedule, I’m now on a flight to Detroit.
I land at 11:20am EST and pitch at 12:25pm EST.
So today, there’s a new mounting pressure that I haven’t felt in a while. I believe, to my bones, that higher education ought to be infused with more real-world experience, and those opportunities should be accessible to students of all backgrounds and demographics. And my team and I have spent years trying different things to support a wider array of individuals. I believe our most recent concepts are the most viable and these resources could help move that work forward.
But will it happen?
Will this be another “almost?”
What story will I write after this experience?
In any case, there’s a mission to pursue. A company to build. A team to support. And students, families, and universities who need this work. That’s what matters.
So whatever happens, I’ll be back next Wednesday.
And I hope you will too.
PS: If you’re in Chicago this Thursday and want to watch the finals at our workspace, WeWork Kinzie, RSVP here.
The first story I vividly remember hearing was, “Where the Wild Things Are” by Maurice Sendak.
I don’t remember how old I was when I heard it. Maybe seven. But I absolutely remember the teacher who read it to me.
She was tall. Thin. Long, flowing brown hair taken straight from a Pantene Pro V commercial.
I remember thinking she was the prettiest woman I’d ever met. I even told her that once.
One day during class…
My teacher asked us to gather on the floor around her chair. Then she showed us the cover of the book and read the title in a gentle voice that now reminds me of Sarah Koenig from Serial & S-Town.
But then something incredible happened. That sweet, calm, endearing elementary school teacher slowly transformed into a one-person theatrical spectacle. As she began reading the story aloud, her voice would rise and soften. And her face would scrunch and stretch.
As the main character, Max, sailed away, she was part of that journey. All of us were.
When Max made mischief, she made mischief.
When the wild things romped. She romped.
When he felt alone. All of us felt alone.
And when the story ended with a warm meal, everyone in the room was relieved.
It wasn’t just the magic of a good story…it was was the wonder of storytelling.
Ever since, I’ve fallen in love with stories — how they’re constructed, written, and shared. And over the years, I’ve become friends and teammates with some of the best storytellers I know. In fact, it’s part of Experience Institute’s curriculum for both our college and corporate programs, which means I get to help other people write and tell compelling stories. Our team has formulas and processes that we’ve shared with literally thousands of people. It’s been a dream.
Recently, I was asked to perform a story at a small private event.
I had one month to write and prepare. But to my surprise, I was stuck. Completely and totally stuck.
Eventually, I decided to break most of my own rules and try something out of the ordinary.
The story recently went live on the podcast that hosted the event. You can listen to the short 5-minute piece here or read the script below.
In any case, it was a good reminder, that stories don’t happen, they are told. And it’s up to us to tell them well.
I hate email.
I try to read and reply as quickly as I can. And I don’t normally reply to emails on Friday nights. Because Friday nights are for friends, not email.
But, on this one Friday night in March, I was working late. It had been a tough week. One of those weeks where nothing seemed to go right.
So for this Friday, I was home. Alone. And occasionally doing my routine phone check.
Then, I see an email from Tanner Woodford. I think the world of Tanner. I look up to him as a person and respect his work greatly. And his email photo is so cool. Seriously. He looks like one those legendary designers who’s been dead for …like…50 years. How can you NOT want to check his email. I’m being emailed by a cool design legend who seems dead but is really alive.
OK, the email….
Hey there! Chicago Design Museum opens its next exhibition on April 28th: Dan Friedman: Radical Modernist.|Leading up, I’m planning a series of events and a small installation at the SOHO House the weekend before it opens. More specifically, on Friday, April 21st at 6:00p, we’re bringing in the Nerdologues for a live storytelling show-turned-podcast. Your Stories will be recorded in front of a small audience in the theater, and features 10 five-minute stories. The theme is “Be Radical.” I can’t imagine the event without you.
Could you let me know by Tuesday if you’re interested in participating?
Thanks so much, and enjoy the weekend!
I re-read the email. Clicked on the links he shared. And realized, this could be cool. So I replied quickly,
Yep! I’m in! I’ll block out the evening of the 21st. Keep me posted on details.
I didn’t realize my mistake until a few days later.
Shit! I have to write a story. A good story. For interesting people. And it’s going to be recorded.
I felt like I’d said yes to going to homecoming with a girl I barely knew and my older brother was chaperoning.
But I couldn’t back out. Because it was for Tanner. Tanner Woodford. I gotta do this.
Now you should know, I write a lot. I love writing.
Writing is to me like running, or yoga, or posting insta-selfies with too much makeup is to the next person. I write nearly every night of the week and I try to publish something every Wednesday morning. It’s my thing.
So I should be good, right?
But every once in awhile, a project turns into that piece of apple skin lodged in the back of your teeth. You keep trying to use your tongue to wiggle it loose, but you really need floss….but you don’t have floss…so you just keep contorting your tongue in weird ways hoping that shitty piece of apple skin will magically be gone and you’ll feel that great victory of not having to go to the store to buy floss.
That’s what this writing project had become.
My first thought was: I have lots of stories to share. I’ve lived this spectacular life where I’ve traveled the world and started a school and worked with big institutions and companies.
But writing about my work felt too…predictable.
So, I sat at my desk and wrote other stories…things like…
Being licked by a lion
Getting stuck in Cairo with 20 teenagers
working as a valet parker and having a stranger offer me $100/hr to smell my feet,
I wrote some of those stories. But, they didn’t quite fit with the theme.
So, I wrote the story of my dad being diagnosed with Stage 4 Pancreatic Cancer, 1 year ago, almost to the day. I wrote about getting the call while having dinner not too far from this spot. I wrote about my mother being handed a stack of papers and a crate of pills and a calendar full of appointments…and handling all of it with such amazing strength… I wrote about my older brothers’ wisdom, and how he’d never hugged me so hard like he did on the day of the funeral, and my younger brother’s hospitality and tenderness with everyone who he visited with. I wrote about how sweet my dad had become during the first few months following the diagnosis. And then how sad and even angry he’d become in his final days. And…I tried to add humorous moments so it wouldn’t be so heavy for you to hear.
But when I was finished, I couldn’t read the story… I just couldn’t.
And… for some reason, writing about cancer for this event seemed like “cheating.” Don’t ask me why. It just did.
I had to move on. … But now the event was only a few days away.
Then, another email. This time, from Eric….the organizer. He introduces himself, shares some house rules about the event, and then…the order of speakers:
1. Nerdologues member 2. Andrew Huff 3. Victor Saad 4. Christen Carter 5. Lloyd King BREAK 6. Alex Cox 7. Sam Rosen 8. Roman Titus 9. Joey Stevenson 10. Constance Volk
Shit, I think. I know a lot of those people. I think all nine of them also had cool email photos. I’m doomed.
I made one last ditch effort:
I went on long bike rides and listened to the Moth stories and past nerdologue episodes.
I tried writing from beautiful places.
I reorganized my bookshelf.
I strategized with friends.
At this point, Tanner is sitting on my shoulder talking to me — (really it’s just his photo…with a moving mouth), telling me this has to be extra funny, cool, inspiring…all without coming across as not trying too hard.
But I realize, I don’t have it in me. That piece of apple skin is still lodged back there somewhere.
So, here I am. Standing in a room full of people I really respect.
At a storytelling event.
And no story to share…
There are a lot of things in life we should be skeptical of.
Too much of a thing.
Things with no consequences.
Shortcuts to things.
Things where the reward is far greater than the cost or effort…
And I agree. You should be skeptical of those things. They are likely too good to be true.
But really good things, the things that are good to their very core, are so pure…they are nothing but absolutely true.
A mother who selflessly cares for her sons, even when she’s dealing with the loss of her husband.
An old couple reaching for one another’s hands on an evening walk.
Seeing a man return to his family in the airport after a tour of duty.
A community of strangers sharing a common bond and rallying for just and equal rights.
Spotting a young couple lingering outside of an apartment building, and finally sharing a parting kiss.
An embrace between people who come from different backgrounds and belief systems.
Catching the sun as it pours its rays through tree branches on an evening hike.
The list is longer than you think. It includes moments when the wrong in the world is eclipsed by the goodness before you. They are the things that spark hope and inspire you to be better.
Those are the things we need more of.
And they are the ones you and I can make. Anytime.
I was recently at an event where the emcee was one of the most memorable parts of the night. And I began to wonder why.
I mean, have you ever been to an event with a great emcee? You know, the person who opens and closes the night and introduces key moments throughout the event.
They’re energetic, they relate to the audience, they talk just long enough to make you feel welcomed and informed, and they may even make you laugh.
But the difference between a good emcee and a great emcee isn’t just engaging an audience, it’s the ability to set the stage for each act.
They research everything about the event. They know the performers, the venue, the city, and specifics about the audience. They take all of that knowledge and use it to build excitement and anticipation for each part of the event.
A great emcee can reference some of the nuances of each act –how the performer is going to use a certain instrument, or where the act originated, or how special it is that they are here for this occasion.
Then, they’ll rile up the crowd.
“So, are you ready for the incredible ____________??”
“Then give it up for ___________and the _______________”
[ Crowd goes wild ]
The connection between a good emcee and a good performance is undeniable.
If an emcee fails at their job, stumbling through details and lacking energy, the poor folks who enter the stage have to start by building that energy rather than launching right into their best work. In some cases, they may never get to those magical moments because it was lost before they even walked on stage.
An emcee holds a lot of power.
And so do you.
Everyone around you needs an emcee. They need someone who knows what they’re good at and can vouch for it in front of friends, teammates, clients, and anyone else looking at their stage.
And not only vouch for it, but also nurture it.
There is nothing more powerful than someone saying, “Hey, you’re really growing in your ability to ____________. So I got you this book…”
or “I got you tickets to this event…”
or “I saw a sign for this program and I think you should consider it.”
Those acts communicate that you believe in them and want them to succeed.
More importantly, the more you get to know about the people closest to your life and work, the better emcee you’ll be during conversations, meetings, and projects. Doing so will deepen and sweeten your relationships and build morale among everyone who’s looking in.
Because the show isn’t just about you…it’s about all of us.
I’m about to make a few changes to how I share weekly writings…but first, here’s a bit more about why I’m here:
Three years ago, I started writing nearly every night of the week. It was a personal challenge I set with one of my best friends and writing partner, Dane Johnson. The practice became one of the most meaningful experiences of my life and we continue it today.
Shortly after writing switched from a bet to a habit, I began publishing one of the more artful or helpful posts every Wednesday.
And with that, Wednesday Words was born.
At first, it was just a quiet space to share personal reflections as I worked with amazing people to build Experience Institute. Over time, Wednesday Words has grown to nearly 1,000 remarkable people from around the world, only by word of mouth.
Cool, but what is Wednesday Words about?
Each week, I share personal lessons and ideas around the Future of Learning & Work.
Since both of those topics are broad, it might be more helpful to know HOW I write. My commitment to you is to be:
Authentic. I share the personal side of things. It’s helpful to remember that learning and work intersect with our relationships, emotions, and overall well-being. As the team and I work together and with a wide array of individuals and organizations, I document stories that tie back to living a full life while pursuing great work.
Consistent. I’ll share a helpful and brief piece every Wednesday morning. Except for the month of December — I’ll explain more about that later. Sometimes, you’ll hear from other writers in Ei’s talented community. But in any case, you’ll hear from us only once a week.
Transparent. Experience Institute has been working in this space for four years. We’ve learned a lot and we’re always trying new experiments, collaborating with remarkable people, failing, and learning even more. Our hope is to share the ups & downs in a vulnerable way that would help you accelerate your own growth and development as an individual, team, or company.
Lastly, these pieces are meant to be helpful. Sometimes the lessons will come in story-form and other times they’ll be quick, memorable notes.
Starting today, I’m going to make a few small changes and invite a wider community to join in:
Here’s what’s changing:
You’ll be receiving emails directly from me (firstname.lastname@example.org). So when you reply, I’ll receive it and I’ll always work to reply to you.
I’m going to begin publishing these posts on Medium. There, you’ll be able to leave comments, make suggestions, and discuss your ideas with others in the community. At the end of every email, you’ll find a button where you can visit the article and chime in. But there’s never any pressure to do so.
If you’d like to receive these notes in your inbox, just click here: bit.ly/wednesdaywords. I’ll share the next Wednesday Words on May 3rd.
Wherever you are as you read this note, thanks for being a friend and sounding board along the way. And thanks for being someone interested in building better institutions, organizations, and companies. I’m excited to continue this journey with you.
Whether or not you know it, you’re really good at beginnings.
You were born.
You began school every fall.
You begin a new year every January.
You begin a new relationship every time you meet someone.
You begin a new chapter with every transition.
You’re good at beginnings because they simply occur over time.
But there’s a difference between beginning and starting.
Beginnings happen because of the forces around you. Starting happens because of the longings within you.
You start something when you feel a pain, see a need, or stumble upon an opportunity. You start a new habit, business, program, action, function, or process.
And whereas beginnings lead to endings, you start something because you want to finish it. And you want to finish in a better place than where you started.
Naturally, you’re not quite as good at starts as you are at beginnings. Starting is harder. It requires intention, community, courage, and a small dose of naiveté.
But starting isn’t as difficult as finishing. Most people have a hard time getting there. Sure, they may end…but to finish is to arrive somewhere you intended. Even if it’s not pretty, it’s powerful. It requires regular reflection, a community, and planning to make sure you’re on the right track.
Unlike beginning and ending, you’ll know when you finish what you’ve started. You will have learned, grown, moved, or changed something.
Because finishing is your doing.
Ending is just time’s doing.
So, are you beginning and ending? Or are you starting and finishing?
PS: This Fall, we’re inviting college students everywhere to not just begin another semester, but to start taking their learning into their own hands through work/study opportunities around the world. Applications for Ei’s new 15-credit Leap Semester program are now open.
Apply here: www.leapsemester.com
Nominate a student here: www.leapsemester.com/nominate.
A few years ago, I joined a club/leadership group called Chicago Global Shapers.
It’s a chapter-based program for young entrepreneurs and leaders founded by the World Economic Forum. I felt way out of my league when I joined and I still do. Over the past few years, we’ve worked together on various volunteer projects in Chicago. And several of the members have inspired me with their work and supported me as I pursue my own endeavors.
But over the past year, my participation has declined. The combination of building Ei combined with an array of personal matters have required more time alone or with close friends and family.
I thought I could fade into the shadows, but that’s a bad way to leave a group – especially a group of friends and peers.
Thankfully, two of the group’s leaders reached out to check in and ask how I was doing and if I wanted to continue participating. They would have had every right to be frustrated, but instead, they were kind and gracious. Our mandatory annual retreat was approaching and they asked if I could participate. When I told them I wouldn’t be able to attend and that I should bow out of the group, they asked if I wanted to share any words with the crew. Another sweet offer.
It reminded me that leaving anything well requires consistent and thoughtful communication. The sooner you communicate, the better. And the more honest you are, the more you keep bridges in tact for the future.
I didn’t do those things, but thanks to those leaders, Elle & Sarah, I had a chance to share the few words below.
If you’re thinking about leaving…
Remember that it’s ok to do so. But do your best to leave well. Address it sooner than later, be honest about where you are and why, and share gratitude for the time you had.
The way you leave may be one of the most memorable and impactful things you do as you navigate your work and relationships. Leave well, and you’ll help everyone involved be well.
Recently, I stumbled on a note from one of my best friends. The note was written five years ago, almost to the day.
In it, my friend spoke about the ways he was seeing me change as I pursued my own endeavors. He was proud of me, but he also cautioned me about newfound tendencies he’d begun to notice. I remember it was a hard note to receive. But it was necessary. Very few people had such a close view into my life as this friend.
It was helpful to read it again five years later. Thanks to a few dear friends, I’ve kept some of those tendencies at bay. But a few of them have become habits and are now things I am now working through. [No, I’m not going to list them here.]
The point is that someone in my life was brave and thoughtful enough to notice my blind spots and call them out. With his help, I saw things I was missing. And even though I’ve stumbled a few times, I’m a much better person because of his courage and voice in my life.
When I think about a strong community like the Shapers, I think about being that kind of voice for one another. Not just people who make things together, but people who work through things together. When we do so, our eyes, hands, and hearts are multiplied by the number of people in the community.
Unfortunately, I haven’t been that for many of you lately. I can blame it on being busy or a personal life that’s taken heavy hits, but there are no excuses. I simply haven’t been able to invest the time that this group deserves. I’m sorry for that.
Still it’s been a joy to be on the periphery. I’ve seen as you’ve worked through audacious Impact Projects, hosted meaningful Learn & Serve events, and kept the group moving forward through leadership changes. And you’ve done all of this by sending a mere 1,364,234 emails. Amazing.
Kidding, of course.
Thank you for letting me be part of such a special group. And thanks for speaking into my life at various times. You’ve given me counsel about Ei’s new programs, helped to launch Leap Kit, given me personal advice, and sent flowers and notes over the past several months. Your kindness is beautiful.
I’ll be stepping down from Shapers, but I won’t be far. If you need a hand, personally or professionally, I’ll always try to help or lend an ear. I know you will too.
And as you spend the weekend together, I hope you will be brave with your words to one another. Listen closely and share the things that need to be said. Your collective courage and investment in one another may be your greatest contribution during your time as a Shaper. It will lead you to your best work in this city and beyond.
In the words of the late Samuel Mockbee, Proceed…and be bold.
Over the past sixteen months, a few friends and I have been working on an idea. The first time we tried it, it didn’t quite work. But starting today, it has another four weeks to fly.
Rather than tell you about our story afterwards, I’m going to share it along the way.
Here’s the idea:
Create a semester-long work/study program that helps college students launch their career earlier while still earning full credit towards their college degree. It’s called Leap Semester.
I know what you’re thinking.
“Isn’t that what internships are for?”
Nope. Internships aren’t fully accredited. A student may earn 3-6 credits. We wanted this program to be a full 15 credits per semester.
“How about study abroad?”
Kinda. Study abroad is fully accredited. But you’re still in a class for the majority of your time.
Both of these experiences can be great. However, we’re curious about students being in the workplace and delivering real work to real companies & organizations, and earning full credit.
Last Summer, our team at Experience Institute and our partners at SAGE Corps ran a prototype without a college partner. It went really well and we knew we were onto something. Then, we struck up a conversation with Columbia College Chicago, a media arts school down the street from our offices.
We worked rigorously to see if we could prototype the program this Spring. We launched in November and had a 2-week window to find ten students. We were on campus nearly every day: in classrooms, in the career center, on sidewalks, etc.
We found students who wanted to participate!
Academia is complex. We learned we hadn’t completed all of the necessary paperwork to run the program together. Also, students couldn’t use financial aid yet.
So we pressed pause and went back to the conference rooms.
The past three months have been packed with meetings, documents, and calls. It’s hard to explain why it was so difficult in a few words, so let’s try an equation:
college leadership + faculty + accrediting bodies + curriculum that will be completed in-person & online + career center + financial aid + travel & housing + companies = OMG
And that’s the shorthand.
More Good News!
As of last week, we have the green light from all parties to try again.
The program is now fully embedded into a college. Students from Columbia College Chicago OR any other higher education program in the country can apply to participate. If they’re accepted, they’ll even be able to use their financial aid to participate in the program (upon receiving confirmation from their institution).
That’s great, right?
It took a long time for us to get to this point. So long that we now have to find a way to find students amidst a busy, noisy end-of-year season. Most college students are in a mad-rush to register for fall classes and figure out summer plans.
Let’s give it a go!
We’ve partnered with the Career Center, the Office of the Provost, our printing partners at Graphic Arts Studio, and a slew of friends to begin spreading the word.
It’s taken a long time and a lot of great people (SAGE Corps, Columbia College Chicago, a group of awesome students, and a few dear friends), but we’re ready to give this a second try.