In March, I joined an online coaching program and met Tomas, a guy who would soon become a close friend.
This weekend, seven months later…I met him in real life.
He’s been sober for six years, so before the trip, I was boasting to my friends that I would save money this weekend by not buying any booze and by going to bed early each night. That didn’t happen.
It turned out that even though Tomas doesn’t drink or do drugs, he’s an incredible host and wingman who loves to have a good time. I felt like I was in college again, a man-sized child lost in the largest city in the country.
I…
• stayed out until 4am each night • played chess hustlers in Washington Square Park • befriended strangers when we were out and about • set up coaching sessions with those strangers • ate mushroom chocolate and woke up tripping with no idea where in Brooklyn I was • got late-night tacos both evenings • left my credit card at the last bar we went to • saw Seth Meyers walking with his son five feet from me in the park • got offered blow by the CFO of VICE • decided I would move to the city about ten times and changed my mind each time
Can I do this every weekend? Absolutely not.
But it’s times like these I never want to give up. I’ll gladly sacrifice my comfort for a day or two for memories and moments like I just had.
It’s lovely to craft a successful career for ourselves. But what is twenty times more important is sustaining fulfilling relationships with other people—friends, family, and colleagues.
“The tendency to interpret new evidence as confirmation of one’s existing beliefs or theories.”
No matter how objective or reasonable we feel our opinions are, this psychological fallacy plagues every single one of us. From our sociopolitical opinions on down, we will always find it easy to find evidence which agrees with us and difficult to stomach evidence which disagrees with us.
With the power of the internet, one is guaranteed to find something somewhere (or a lot of things in a lot of places) that confirms what they already believe.
There are entire flat-earth communities. Q-Anon has over 10,000,000 members.
Mark Manson said:
“You used to have to go to medical school for two years to have an opinion on a vaccine. Now you just scroll through Facebook for 20 minutes.”
He’s right. Today, a person can decide what their opinion is, look at their phone, and find millions of people around the world who support and agree with them.
I hear people spouting their opinions with the confidence of a seasoned expert. Then, after a few questions, I see how shaky their arguments are.
So how do we combat this? The answer isn’t super fun.
It’s exposure.
The healthiest and most challenging thing we can do is spend intentional time researching the other side…
• Google “{my opinion} debunked” • Have curious conversations with people we disagree with—for the sake of hearing new perspectives, NOT with the goal of changing minds • Listen to podcasts/read books that challenge our beliefs
I’ve spent many hours doing all of this in 2021. This shit is hard.
It’s not mentally or emotionally enjoyable to pursue ideas which disagree with the ways we see the world. But it sure is healthy. It:
• strengthens our curiosity muscle • lessens our tendency to be triggered by those we disagree with • shifts our value of “being right” toward learning new things
Try it out. What are some opinions you would be uncomfortable putting to the test?
Two weeks ago, I ran a workshop on people-pleasing, saying No, and protecting our time and energy.
It was lovely to hear a group of friends, family, and colleagues collaborate and share stories and ideas.
The underlying notion of the conversation was that people-pleasing is bad and should be avoided. But then one of my coaching friends posed a challenge.
“I think people-pleasing gets a bad rep,” she said. “Sometimes it’s totally justified to do something we don’t feel like doing for the benefit of ourselves and especially others.”
I needed to hear this.
In the self-improvement and entrepreneurship worlds, it’s normal to hear things like:
• If it’s not a Hell Yes, it’s a No. • No is a complete sentence. • Say No to most things.
What I realized as my friend was sharing her thoughts was that all these ideas are contextual. If we’re running a business, these rules are quite helpful. We can’t say Yes to every opportunity. We’d get distracted and pulled in too many directions.
But part of having healthy and fruitful relationships is being selfless for those we care about. Again, my friend made an excellent point:
“If you say No to five invites in a row, don’t get upset when your friends stop inviting you to things. Plus, how many times have you gone to something you didn’t want to go to…and you ended up having a lovely time?”
I love when I have my mind changed. Since this discussion, I’ve been more cognizant of saying Yes to things which would bring me closer to people…without burning myself out.
The book I’m currently writing is a decision out of necessity.
Over the last four years, between myself, my friends, and my colleagues, I’ve witnessed a disappointing phenomenon. It has to do with the fact that regardless of our skills or interests, every single one of us wants to create something.
A more fulfilling life, a business, a blog, a podcast, anything…
For 24 years, I repeated the notion—in my head and out loud—that “I’m not a business person.” I don’t get it. I’m not business savvy. I could never run a successful company.
Eventually, between obsessing over self-improvement and getting yelled at by Gary Vee enough times, I decided I wanted to try this here business thing.
But I had no fucking clue how. How does one just create a product or service and find customers to sell to? The answers eluded me. So I read every business book I could find.
They pumped me up. I learned so much about the mindsets and habits of productive CEOs and founders. I did this for two years, crafting the perfect library of knowledge.
But I looked around and noticed I still had no service and thus no customers. That’s when I realized what was holding me back. It wasn’t my lack of information. It was me.
I was waiting for permission to create what I wanted to create.
I knew way more about running a team than the kid on my street corner manning his lemonade stand…but that kid was actually doing the damn thing. I was merely imagining doing it.
He wasn’t comparing himself to his friends’ LinkedIn pages. He gathered a base of understanding, got some help setting everything up, and started selling.
We think we need more information. What we really need is to dive in and learn as we go.
We don’t need anyone’s permission to start something. We can just start.
Most people are willing to have difficult conversations, be vulnerable, and put themselves out there.
The problem is, most people are unwilling to be the initiator of these things.
A powerful skill I’ve developed this year is that of being the initiator.
• Asking for the things I want. • Setting up plans and events. • Being active, not passive.
So many of us choose our path out of fear disguised as practicality. What we really want seems impossibly out of reach and ridiculous to expect, so we never dare to ask the universe for it.
That summer was a crescendo of 23 years of me having no defined values, no direction, and no true skills.
I would talk and think endlessly of all the things that could be…while at the same time ignoring my way through life. I wasn’t getting any actual work done.
After a handful of pills and a fifth of Jim Beam, I woke up two days later with both staggering fog and utter clarity. “This has to change,” I mumbled.
But what I quickly came to realize was that that desire was backward. I had been waiting my whole life for this to change. And waiting around hadn’t gotten me far. So I turned to what is now my favorite cliche…
If we want something to change, we have to change.
It’s so stupidly simple. But what I’ve seen in a lot of folks—including myself—is a longing for transformation while living with the same habits, routines, and thought patterns as the month before.
The change starts with us. There’s nothing out there that’s going to make it happen for us.
In the world of business, there are naturally people who do sketchy shit to acquire wealth.
But the majority of folks do so by following the golden rule of making money.
To make more money, bring more value to more people.
I have more positive feelings toward my local used book store than I do Amazon. But Amazon has received much more of my money because I must place more value in fast shipping, eBooks, and streaming services.
In a restaurant, a server tends to make more than a dishwasher because they have more impact on whether customers enjoy their dinner and whether they want to return or not.
Want to make more money? Bring more value to more people.
This weekend, my photographer friend told me he’s making the decision to start posting on Instagram again.
I deleted mine last year because it was sucking too many hours away from my days. But this was a monumental move for him for a different reason.
He obsesses over who likes his pictures and over how many likes they get.
“There’s nothing more pathetic than scrolling through the list of likers several times a day,” he joked. This hit home.
There are two types of people who post on social media: those who check the likes, and liars.
While he didn’t ask for my advice directly, his predicament got me thinking…How do I manage to post consistently and not let the dopamine/validation/comparison train run me over?
Two things came to mind…
1) Be clear on the intention.
Why do we post something?
For my buddy, he said it’s fun to show his work. He has a skill for taking photos and he’d like to share that with friends and colleagues.
For me, I love sharing lessons I’ve learned. I write this blog every day except on Sundays. In the hopes that they resonate with someone who reads them, I post my favorites (including this one) to Facebook.
It doesn’t happen with every blog, but the most rewarding aspect of sharing my insights is when someone reaches out to tell me how a particular idea landed with them. This means they didn’t just read the words, they felt the emotion beyond them.
But above all, I write this blog every morning to dump my thoughts. It’s a way of holding myself accountable for a journaling habit. It helps me articulate and communicate better in other areas of my life.
If we’re going to create something and share it with others, we have to like it first.
Call me douchy, but I like my blogs. I enjoy reading them. I couldn’t do this every day if that weren’t the case. And I would’ve certainly quit during the early months where no one was reading them had I not simply enjoyed writing them.
When we start creating something, it’s probably shitty. Mediocre at best. People aren’t going to be too interested.
Since that’s the case, we better love it. If not, if we instead focus on creating something we hope others will love but we detest…now it’s a lose-lose. They don’t like it and we don’t like it.
The simple process is this:
Start creating something we enjoy.
Do it consistently and get better at it.
Share it.
People will slowly begin to stick around to hear what we have to say.
Repeat.
If the intention is something we can’t control—money, subscribers, likes—that’s unsustainable. If we just keep at something we love doing, all that shit will come later.
2) Understand we’re human.
The human brain takes millennia to evolve. The meat in our skulls is pretty similar to that of our ancestors from 30,000 years ago.
Yet we live in an impossibly advanced society. Our technology has improved more in the last 20 years than the previous 200 before it.
The world around us is moving at rocket speed and we’re still running with software that has yet to be updated. We crave instant gratification, acceptance, and importance.
What’s more, our billion-dollar social media companies know this. They pay people millions of dollars to exploit these natural human weaknesses which keep us looking at our devices. We feel good when we get a like. Someone has shown us approval and belonging.
This may sound a little depressing, but all I’m saying is…
We’re not morons for checking our phones. This shit is designed to be addicting.
TL; DR.
If we’re questioning our social media usage, we can simply ask:
We often think we want things that don’t actually fill us up.
We may desire to:
• run a thriving business • read a book every week • be in impeccable shape
But there’s a lingering question in all this…
Do we actually want to do what it takes to do this, or do we merely enjoy the idea of it?
I thought I wanted to be a full-time YouTuber, so last year I did a daily vlog for two months. I burned out hard and realized I fucking hated it. This felt crushing because I would watch Casey Neistat’s videos and feel like I didn’t have enough grit or determination to achieve what he has.
Comparison aside, I had to come to grips. I wanted the result but resisted the work needed to get the result.
What I wanted:
• millions of subscribers • a community • ad revenue
What I didn’t want:
• to shoot scenes • to be “on” all the time • to edit for hours each day
So what does this mean? How can we look forward to the boring and mundane stuff?
I love running a coaching business, playing chess, and working out. Even when I don’t.
It’s okay to not like the things we think we like. We just have to find the work we like.
This week, my best buddy and I did a feedback exercise.
It’s where we send something like this to the people—friends, family, colleagues—who know us best:
Hey! I’m doing a research project and could really use your help. Would you mind answering these questions… What do you think my biggest strengths are? What do you respect/admire about me? What do you think my biggest blind spots are? What can I be doing more/less of? If you were me, what would you make a priority?
Seeking constructive criticism accomplishes a few things. All great.
1) It helps us grow as people—personally and professionally.
2) It gives us a clearer picture of the lens with which the people around us view us.
3) It can solidify the things we already know to be true.
4) It really highlights our strengths.
Naturally, this should be done with folks we trust to have our best interests at heart.
When he dove into my strengths and blind spots, much of what he said surprised me. Things like:
• Great at first impressions • Excellent teacher • Should surround yourself with more people who take initiative • Should prioritize paying off debt sooner
We’re cursed with only having one set of eyes to look down upon our lives. Getting other perspectives from the people who care about us is a powerful thing.
• Income: vital, growing • Savings: not enough, a little each month • Debt: mountain, heavy • Toxic money: none really • Income goal: $100K+, relief, safety, freedom
The coolest part about this exercise is how many of my responses surprised me. Try it and see what thoughts pop up.
I held a workshop last night open to a bunch of my friends, family, and colleagues.
Few things delight me more than connecting people who otherwise would’ve never met.
Hearing one of my coaching friends say, “I loved what Karen said…” made me smile. I was like, That’s my aunt!
I’ve learned a few things from running group calls:
1) People love talking and engaging, even if they think they don’t. It makes the time pass quickly and people enjoy gaining different perspectives on the same topic.
2) The worst thing a curator can do is ask the group: “Does anybody have any thoughts?” Just fucking call on someone. They will share their thoughts. Don’t give them a choice. The six seconds of silence after that question is asked is valuable collaboration time. I call on folks at random every time and no one has ever said, “I actually don’t have anything to say.”
3) The more I prep and plan a group call, the more flat and robotic it sounds. My best calls have been where I’ve let the momentum of the conversation take the wheel. It may be slow at the start, but once people begin sharing, it becomes a flywheel that spins itself.
Yesterday, I’m quite certain I experienced the effects of sleep deprivation for the first time in my life.
All three nights this weekend, I attended an event that led to me staying up late. Two of those nights I drank alcohol which always fucks with my sleep quality. And according to my tracker, I averaged four and a half hours of time spent asleep Friday through Sunday.
So what was yesterday like?
The Sleep Foundation lists these as the major symptoms of acute sleep deprivation:
Slowed thinking
Reduced attention span
Worsened memory
Poor or risky decision-making
Lack of energy
Mood changes—including feelings of stress, anxiety, or irritability
That sums my day up perfectly.
In the morning, I sat down with my cup of coffee and for the first hour of my day, I had to constantly remind myself of what I was doing. I would start one thing and jump to another, forgetting what I was doing in the first place. The pit of anxiety in my chest was thunderous.
At noon, I hopped on my regular Monday call with my coaching program and I don’t even remember what we did or what I said on it.
When that was over, I began my next three hours of work, made it about ten minutes, threw in the towel, and went and laid in bed.
I can’t remember the last time I started a day of work and then stopped in the middle of it. Unfortunately, this didn’t calm me down because my chest was telling me I should be working harder, not resting.
Ugh.
Why is this blog post called what it’s called?
It’s because it doesn’t matter how much I talk, write, or preach about how vital it is…sleep always seems to be something that’s easy to sacrifice.
Yesterday humbled me. So today, with my rested and refreshed brain, I’m writing down a few rules for myself on my whiteboard:
1) At 10pm, the phone must be on airplane mode.
2) If there are coaching sessions scheduled the next day, no more than two drinks the night before.
3) If an offer or request doesn’t light me up, I have to say No to it.
If we want to prioritize our energy, we have to treat it like a priority. That’s what yesterday taught me.
When I talk to people about creating content, starting a business, or improving a skill…I make sure to bring up the difference between Action and Motion.
Action is doing the things we actually need to do to create what we want. Motion is preparing and planning to do those things.
Both are necessary, but all too often I see people stuck in the Motion hole.
• “I want a girlfriend, so I’ll get a gym membership.” • “I want to start a blog, so I’ll research all the best website builders.” • “I want to run a business, so I’ll read the top five business books and create the perfect business plan.”
Learning and giving ourselves a base is absolutely necessary. But in order to actually get what we want we have to just dive in.
Motion tends to make us think we’re doing something productive, when we’re really just procrastinating the Actions we’re scared to take.
If we want a girlfriend, we need to talk to and ask out more women.
If we want to start blogging, we just need to pick an easy way to publish and start writing.
If we want to run a business, we need to find people who will pay money for our product or service and sell it to them.
95% of what we need to know will come from Action and experience: getting rejected, writing shitty blogs, and making hundreds of mistakes.
When we need growth, we don’t need more preparation; we need to take more Action.
I started dabbling with affirmations last year. I thought they were total bullshit.
I’ve never been into the idea of manifestation or the law of attraction. Naturally, we should have a clear vision of what we want…but the only way to make it happen is to consistently do the work and actions necessary.
We don’t manifest a healthy body. We exercise and eat well to create one.
We don’t manifest more money. We provide more value and change our financial habits to create more money.
We don’t manifest better skills. We practice until we get really fucking good at them.
….BUT affirmations don’t have to be about wanting something from nothing.
On New Years Day, I decided that my life would have a new mantra. I wrote it down in my notebook and have continued to write it every day since:
“I love doing scary things.”
Has this turned me into a fearless and rich person? Absolutely not. But, whenever opportunities or risky ventures have presented themselves to me this year, I’ve simply reminded myself that I love doing scary things.
I’ve never taken more intimidating (to me) action in my life than in the past eight months. I’ve…
• started a freelancing business • halted that freelancing business to go full-time with my coaching business • paid $12,000 for coaching programs • put myself out there as a coach to a bunch of people from my past—getting ignored and rejected constantly • started running group coaching calls/workshops • bought plane tickets I couldn’t afford • did a triathlon • wrote this blog every day and shared my favorite ones • told a woman I had feelings for her • started writing a book • built an established business when, my whole life, I’ve said I know nothing about business
What I’ve learned from this:
Affirmations aren’t bullshit if we use them to guide our mindset toward taking more action. Simply writing things that sound powerful isn’t enough, but if we do something about it, those words can change our lives.
We don’t have to be fearless; we have to be courageous. Fear is natural, but we must not let it stop us from creating the life we want to live.
Sleeping in is one of my least favorite things to do.
When I wake up—regardless of how tired I am—I prefer to just get out of bed and start my day.
But for some reason, last night I only got about four hours of sleep. At least that’s what my sleep tracker said when I first woke up at 6:30 this morning.
I made the split decision to do something I never do.
I texted my friends to let them know I couldn’t join them on our weekly swim. Then I set a new alarm and went back to sleep.
Thank God I did. I don’t feel amazing right now…but I certainly don’t feel like the zombie I was when I first woke.
The lesson:
Living a productive life is great and all that….but sometimes we just need some extra rest.
It’s four weeks into writing my book. Here’s how it’s going.
I’ve interviewed four people so far. All have been amazing and each conversation has brought me back to my days of podcasting.
From super successful business owners to folks who have dedicated their lives to helping others in need…I love listening to people talk about what they’re most passionate about.
That’s been a pattern I’ve noticed. We tend to continue creating things we love. I don’t know many painters who just do it to make some extra cash. Maybe we start something to help pay the bills, but we can only sustainably keep it going if we love the game.
Another thing that keeps coming up is this idea of convergence. It’s where the answers to three questions meet.
Those questions are:
1) What are you really good at?
2) What do you love to do? (i.e. What excites you?)
3) What can you do that people would pay money for?
Answering each of these questions provides powerful ideas of what we can do with ourselves.
As I interview these badasses, I’m noticing the things they create passionately align with this convergence.
After showering and getting dressed for my three back-to-back coaching sessions in the morning, I sat down in my office. Of the three calls scheduled, one canceled last minute, and two didn’t show up at all. 0/3.
Sometimes I welcome a canceled call for the extra free time. But three in three hours took an enormous mental toll.
Waves of financial anxiety and doubts of self-worth came rushing in. I even made a Twitch account out of spite. I mumbled: “Stupid coaching. I’ll just be a streamer. Coaching is stupid anyway…”
Whenever this happens it feels like two entities are competing with one another: Logic and Emotions.
Logic was telling me:
• This is not even close to the end of the world. • Lots of people in lots of places have it WAY worse than you do right now. • Why are reacting this way? • People would kill to have your problems.
But despite all this, my Emotions kept rubbuting:
• This fucking sucks and I’m sad.
I felt it in my eyes and face. It was like my vision was slowing down.
Luckily, I had a fourth session scheduled in the afternoon. My goal was to not bring any of my energy from the day into our conversation.
We did our session and it was amazing. He had incredible insights, he made me laugh, and we had a lovely deep dive into his thoughts and fears.
Only after we finished did I tell him about my day. He said he could tell something was up simply from my body language when we hopped on the Zoom. I thanked him for his time and for making my day better.
In the evening, two of my best friends invited me over for dinner. I was a bit nervous because I was doubting my ability to have a clear and present conversation.
On top of that, one of the friend’s dads just had a funeral. How could I deserve to complain about my day when she just buried her father?
It’s not a competition
We swapped stories and it was bittersweet to hear her discuss the anxiety and closure-filled week. When she asked about how I was doing I figured I’d just be candid and open up.
They both listened to every word I said and showed nothing but love and support.
When I admitted it was weird to talk about my “problems” knowing they had just gone to her dad’s funeral, she immediately responded: “It’s not something to compare.”
Really good peoples.
We drank wine and played with their dog and my grey day drifted off like storm clouds. The tension in my eyes was gone. I just felt grateful.
Lessons
1) It’s possible to both a) acknowledge our good fortune and b) feel sad…at the same time.
2) One of the most important things to have in life is friends to whom we can open up wholeheartedly without being judged or scorned.
3) We will never arrive at a day where we’re completely safe from shitty things or negative emotions. We can only improve our skills in handling them and ask the people around us for help.
I went on a lovely family vacation this past weekend. Lakehouse, swimming, tubing, laughing.
But the most memorable moment came when I walked down to the boathouse to find my Grandpa standing at the bottom of the walkway. It looked like he was mentally preparing himself to ascend a mountain.
He had just gotten a pacemaker put in days before. I asked him what was up.
He told me he gets out of breath easily and so I held out my hand to help him up the steps. Once we made it up the first section, he thanked me and assured me he could take it from there.
“All good Gramps,” I responded. “We’ll go up together.”
We got to the deck and he took it from there since he had the handrails to balance himself. I walked back down to the dock to grab the beer I wanted and I noticed I was crying.
It wasn’t a sob. My mouth wasn’t moving. But tears streamed out of both eyes.
This was the first time I got a ‘slap in the face’ reminder of the universal truth: Our time is limited here.
A new lens
After that happened, I saw my Grandpa in a different light. I already love talking to him. He’s hilarious and one of the cleverest men I’ve ever known.
But for the rest of the weekend, I didn’t just enjoy my talks with him…I cherished them.
Every joke and story he told, I found myself uncontrollably beaming. I also looked at my calendar to find the best weekends in the coming months to drive down and visit him and my Grandma.
On top of that, I did some math.
My Grandpa turned 80 this year. Assuming he lives to be 90 years old, I have 10 more years left with him. But that’s incorrect.
On average, I see my Grandparents three times per year. Maintaining that trajectory, I don’t have 10 years left with my Grandfather…I have 30 more visits.
After this weekend, I can check off one of those boxes. 29 to go.
Is this depressing?
No. Not to me.
Talking about this shit is sad, yes. But I much prefer to be open and candid about the inevitable, rather than bury my head in the sand and pretend like death doesn’t exist.
I know people who do the latter and they tend to be the ones who shut down when the worst occurs. Not productive.
Understanding that we’re all approaching death isn’t morbid. It’s empowering.
It forces us to desire more presentness, listening, and compassion.
It invites us to say “Yes” to the things that matter more often: trips with friends, phone calls with family, playtime with kids or pets.
We can obsess over the number of checkboxes we have left with the people we love…or we can focus on the quality of each of those boxes before we check them off.
Having people we love who are alive is a gift. We get to call them, laugh with them, disagree with them, hug them, learn from them…
Even with someone we don’t particularly like—if we found out they had a month to live, we’d forgive their faults and forget our grievances with them. We’d hear what they had to say and make sure they were comfortable and cared for.
What if we did that more often with more people?
Conclusion
It’s up to us to enjoy the box we’re currently checking.
I’m not dreading the number of boxes I have left with my Grandpa. I’m ecstatic for the next box I get with him in a few months.
I coached a fellow coach yesterday who said she wanted to leave the session with enough confidence to do x, y, and of course…z.
We started exploring.
What’s your definition of confidence? What does it look/sound/feel like?
When in your life have you been truly confident?
How much confidence have you decided you need before you can take action? On a scale from 1 to 10?
She told me about her career as a teacher. She studied education for seven years and then jumped into teaching kids, year after year after year. She said when she stood up and taught a classroom she knew who she was and what she was doing.
I reflected back: “It sounds like you gained tremendous confidence after learning and practicing something for many years…And now you’d like that same level of confidence with something you’ve only just started.”
We explored further.
She explained that as a teacher, she could provide the answers, but as coaches our job isn’t to give away solutions but to help others discover the solutions they already have access to.
She had an insight: “When I’m coaching, I’m not the teacher. Life is the teacher. I’m just supposed to be with them in that space where they can learn their own lessons.”
“Holy fuck,” I said. “That’s awesome!”
When I asked her what her biggest takeaway was, she responded without pause: “I don’t need to worry about confidence. I need to focus on authenticity. I’ll show up as me and practice until I get really good at everything I want to do. The confidence will come.”
Sheeeeesh. I wanted to her hug through my laptop screen.
This was such a lovely example of overcoming one of the most powerful stories we tell ourselves: I need more confidence so that I can…
Don’t get me wrong, confidence is amazing. The flow that comes from a belief in oneself can be euphoric. But it’s not a prerequisite for taking action, it’s a byproduct.
Natural talent is fun, but most of our confidence comes from doing something a lot and getting better at it. When we think we need more confidence what we really need is more practice.
