4 questions to avoid repeating mistakes

A table full of writing utensils

It’s been a while since I emailed you guys a blog. 11 days to be exact.

While I’m sure some of you are delighted by this, it’s left me feeling guilty. When you subscribe to something, you do so because you expect value from it.

Some of you support the blog financially. Some of you neglect your children and careers just to read what I write. I’m so grateful.

The truth is, I put too much creative work on my plate at once. Here’s my to-do list from the last 30 days:

  • finish rough draft of Do The Thing!
  • restructure my community’s website
  • write 2-3 blogs per week
  • edit YouTube videos, podcasts, and TikToks for YGG
  • manage new clients in my coaching business
  • go on three vacations with my friends and family

Too much.

But now that I’ve crossed off a few of these items, I’m ready to clean up, reflect, and make sure this doesn’t happen again. I thought today’s post would be a good time to do an exercise I found on Instagram.

It’s called the AAR Method (after-action review) and it’s used by the Navy Seals. It’s a four-question framework. In sharing the model with you all, I’ll give my answers for each step.

1. What did I intend to accomplish?

I tried to move in the direction of what I want my work life to look like.

It’s threefold:

  1. writing blogs and books
  2. running a podcast/YouTube channel
  3. having my one-on-one coaching business

To me, it’s a fulfilling cocktail of conversations and deep work.

2. What happened?

I started sprinting in this direction with no real plan and with little help. My schedule and timelines were up in the air. I got to things when I could get to them.

Problem was, I often felt creatively empty after spending hours of bandwidth on one or two things. I also felt the effects of task-switching. After hours of writing in the morning, coaching in the afternoon, and editing in the early evening, I’d be absolutely drained by 5pm.

3. Why did it happen that way?

I didn’t create any organized systems for keeping everything on track. With everything left to chance, my days were cluttered and sporadic.

I also just expected myself to be able to handle all this. There are these sexy Instagram-worthy archetypes of entrepreneurs doing a thousand things and working 12-hour days.

In reality, most of us have about four to five hours of deep, undistracted work in us each day. So putting eight hours of writing and editing on the calendar was destined to fail.

In summary: unrealistic expectations and a lack of organization.

4. What will I do next time for a better outcome?

Give each day of the week a theme. On these days, I write. On those days, I edit.

Some sort of digital system would also be useful for deadlines. I’m working on that with services like Evernote and Trello.

Finally, next time new projects present themselves, I’ll ask myself: “How much harder will this make things for me?”

I usually go to great lengths to keep from being busy or overloaded. I’d like to never get there again.

I think these questions will help.

The simple rule that helps me get work done

A typewriter on a desk

I tend to work on a ton of things at one time.

Studying chess. Building a coaching business. Writing a book. Running this blog. Launching a new YouTube channel and podcast soon (more on that later this week).

Getting distracted can be quite the wrench in my day. So aside from a few of the popular tricks and tips—a Pomodoro timer, starting small, leaving my phone off and in the other room…there’s one rule I follow that makes everything else 10 times easier.

I stole it from Niel Gaiman, the prominent fiction writer.

When he’s writing a new book, he sits down and gives himself two options:

  1. write
  2. do nothing

That’s it. He can’t do anything else.

The freedom to not write removes any guilt associated with not getting work done. And it doesn’t take long until writing becomes less boring than just sitting there doing nothing.

I do the same.

When I’m not doing whatever deep work is needed from me, I’m sitting here daydreaming and talking to myself. Sometimes it lasts 60 seconds. Other times it lasts 20 minutes. But eventually, I always come back to the task at hand.

The impulse to check something is omnipresent. Email. Facebook. YouTube. Facebook again.

But those aren’t one of the options.

The rule must never be broken. Otherwise, it’ll be broken every day. So instead, I sit here and work…or do nothing.

Done, or perfect?

My friend and I are recording a podcast episode today. Our first one didn’t go so well.

It wasn’t absolutely cringe, as the kids say. But it was tough to listen back to.

We gave too much backstory. We didn’t interrupt each other enough. It felt like we were taking turns giving TED Talks.

But we wanted to start a podcast simply because we enjoy our conversations and hope others would too. Something happens when you hit “record,” though. When you see that blinking red light, the butterflies settle in. It’s easy to feel like everything spoken must be funny or groundbreaking.

I’m so glad we had a mediocre first recording. We can’t grow or improve until we run a test and gather data.

We could’ve prepped and planned for months, trying to create the perfect conversation. But what we did was so much more efficient.

We said fuck it, let’s just do it and see what happens.

Done is better than perfect. Because perfect usually means doing nothing.

The 10 qualities of a Professional

According to Steven Pressfield, there are amateurs and there are professionals. Here’s what sets the pros apart:

1) We show up every day.

Vacations are nice and rest is necessary. But inside those boundaries, we’re on the clock.

2) We show up no matter what.

Again, time away from working is rejuvenating. But if we only do the work when our bodies feel like it, we’re doing ourselves (and those we serve) a disservice.

3) We stay on the job all day.

Our to-do list should be reasonable and doable. And our day ends when it is complete, not when Resistance begins to settle in.

4) We are committed over the long haul.

Perhaps we’ll be doing something different a year from now. But we’ll still be working consistently with purpose, providing value, and growing our skills.

5) The stakes for us are high and real.

We don’t create because it’s a hobby. We create to pay our rent, buy groceries, and afford trips with our friends.

6) We accept payment for our labor.

We are here to serve people and solve problems, yes. But we must be compensated for doing so. Otherwise, we’re not working; we’re running charities.

7) We do not over-identify with our jobs.

We write. We collaborate. We design. We’re not writers, collaborators, or designers. Our work is not our life; it fuels our life.

8) We master the technique of our jobs.

We improve each week because we know we’ll never know all there is to know. We become black belts in what we do.

9) We have a sense of humor about our jobs.

While the stakes are high, we don’t take ourselves seriously. We shrug off failures as part of the game. If we’re getting pummeled it’s because we’re on the field and not in the stands…and we’re grateful for that.

10) We receive praise or blame in the real world.

Some people love what we’re doing. Some people despise it. Both are okay. We appreciate the kind words and learn from or disregard the nasty ones.

I certainly don’t embody all ten of these each and every day. But all I can do is take care of myself and remind myself of the simple truth…

That the hardest thing to do in the world is to sit down in this chair and do the work.

Ideas vs. execution

Dillan Taylor's business ideas

I have a running list of business ideas in my Notes app. I’ve done nothing with 99% of them.

People can be super protective of their ideas.

But ideas are cheap. They mean nothing. They’re just words on a screen.

I don’t even know what some of these ideas mean. “1 hour blog or copy editor”??

Anyone can write a sentence in their phone. Execution is an entirely different thing.

Coming up with ideas is safe. It’s fun to fantasize about these things coming to life.

What’s scary is trying to make them happen.

I loved the idea of building a coaching business. I didn’t love putting myself out there and trying to get people on a call with me (at first).

When people are coming up with business or content ideas, my advice is always the same:

Just help one person. If you can get one person to give you their time, money, or attention, then you can get two.

And so on.

But people spend all their time in the blueprint and strategy stage. That’s a brilliant way to get nothing done, but to feel as though a lot is getting accomplished.

Up late with no regrets

Jorge Masvidal and Colby Covington fighting in UFC 272

This Sunday was the first Sunday in a year where I intentionally scheduled nothing.

Coming into the weekend, I realized that meant I could do something I haven’t done since January 2021.

Watch the UFC fights.

It’s the only sport I care to pay for and make time to watch. When people start talking to me about football, I usually stop them in their tracks. (Is Brett Favre still playing?)

Since the fights are almost exclusively on Saturday nights, I’ve had to skip out on them. They run late, usually ending around 2am.

That’s not conducive to waking up at 6am to prep for morning and afternoon sessions. I didn’t have to worry about that this weekend.

On Saturday, my buddy and I competed in a chess tournament. He did great, going 4-1 and securing third place in his section. I did okay, with two wins and three losses.

We got a late dinner and some beers. He asked if I wanted to hang with him and his roommates at their place to watch the fight. No, in fact, I did not want to do that.

Instead, he dropped me off, I made a vodka drink (not a whiskey drink), and bought the fights.

They were incredible. It felt like an old piece of me I loved was awakened. I was standing up and cheering in my living room.

On paper, it sounds quite lonely to pay for a UFC card, drink a cocktail, and stay up late all by oneself. But it was me-time I’ve been craving for months.

I woke up Sunday morning much later than normal—around 9am. I was groggy and slightly hungover (from three drinks, thanks 28 years of age).

And I was happy.

There was nothing on my calendar. I had nothing to do. I drove back to Baltimore to pick up my jacket and sunglasses I left at the tournament the day before. It was a gorgeous day. A best buddy called me and we chatted for two hours. I read a comic book. I listened to a podcast.

I got nothing done. And it was a productive day.

Productive for my mind and soul (whatever that means). It was peaceful. I could get used to this.

Today, I feel well-rested and ready to jump into the week. I’m a fan of taking weekly vacations—which I think normal people just call “weekends.”

I don’t know what the balance is

Stones on the beach balancing on one another

I hate hustle culture. Obsessing over productivity. Getting shit done. Making moves. Creating projects, relationships, and wealth.

I also love it. I crave it…when I’m in the mood.

There are weeks where I’m on my computer all day working on this or that. Not because I feel I have to, but because it’s fun.

There are also weeks where I’m so burnt out, I don’t give a shit about anyone or anything.

Do we have to work 40 hours a week to build something meaningful? Absolutely not.

But I do think there’s merit (especially when creating our own thing) to working pretty damn hard? At least in the beginning.

I’m in a good place with my coaching business. A huge part of that was my willingness to flood my week with calls and work on weekends. That allowed me to coach more people and be more available to opportunities.

However, I’ve hit a point of diminishing returns. Now, working on weekends, always being on…it deflates me. I had my day in the sun with it. But it no longer serves me. It got me here. And it’ll keep me here.

But the only reason I’m able to message my clients and tell them “no more Sunday sessions” is because I’m totally in a place to do so. I’ve earned it.

And that’s the keyword here. Earn.

We don’t get something from nothing. We don’t get promoted on our first day.

So the question for me is: What’s the balance between working hard and not destroying ourselves?

I’m sure the answer is different for everyone. I’m still trying to figure mine out.

The perfect morning

It is my birthday. And I couldn’t be happier with how I’m spending the morning.

Phone is off. Coffee is hot. I just read my favorite book for 20 minutes and am now writing in my fourth favorite blog.

I got too fucked up this weekend in NYC. No alcohol for a while.

After slowing way down, I’m ready to use the new boundaries I set to put my head down and build something special. The fire is rekindled. I’m in the mood to show up as a professional.

Resistance can’t win. It doesn’t stand a chance.

I’m 28. And time is only continuing to tick.

Here’s to another year!

Boundaries

If we set boundaries, people will meet them.

I’ve been slowing things way down in my business this year. Everything out of necessity.

I stopped taking on new clients in December. And now I’m experimenting with new guidelines to free up time, energy, and bandwidth.

I asked one client if he was okay if we went from two sessions a month to one. He was fine with it.

I told my weekend clients I’d no longer be doing calls on Sundays. They were fine with it.

When people ask me for a call past 3pm, under no circumstances do I accept. I also have a maximum of three sessions per day. No more.

What shocks me every time is how okay with these boundaries people are. Most people are willing to do most things, we just have to ask for what we want.

But we have to ask.

Wordle

I’m on the Wordle train.

As someone who tends to get addicted to games, this one is perfect.

You can only play once per day. Usually no more than five minutes.

Try it out.

New principles

A man in a suit sitting and working at his desk

Last week, I watched this video on non-negotiable principles.

The dude in the video—Alex Hormozi—is super bro-y but he provides a ton of gold. The video made me consider my business’s principles.

I’ve had them written down on my whiteboard since the start of the new year. I realized five was too many. I couldn’t even name them off the top of my head if someone asked. That means they were just sentences that sounded nice.

So I trimmed them down to three.

1) Curiosity before solutions.
2) Help people so much, they don’t need me.
3) Take nothing personally.

It’s not like customers and clients are going to start flooding through my door now that I have three principles. But even seeing this refined list on my whiteboard makes me feel clear and established as to what I stand for.

If I hire people in the future, I now have a set of must-haves. My favorite line from the video is:

“Most people shouldn’t work for your company.”

Because most people won’t embody all three of these principles. That’s okay. It’s about finding the ones who do.

We don’t need to run a business to have two or three core principles, though. What are yours?

I’d love to hear them.

The importance of bosses

Dillan Taylor's boss at the Cheesecake Factory, Mark Milecki

When I had a job, I always thought it must be pretty challenging to be someone’s boss.

I expected them to…

  1. Be a confident and competent leader.
  2. Express kindness and care toward their employees.
  3. Maintain an organized system.

That’s a lot to do all at once.

I’ve worked in restaurants, at a home remodeling company, and on a farm. I’ve had phenomenal bosses. I’ve had terrible ones.

A good leader can be the difference between dreading going to work and looking forward to it. A strong captain can make us feel safe. They can even become a mentor to us. I still keep in touch with the best bosses I’ve worked with.

The #1 reason people quit their jobs is because of poor leadership. Here’s a graph that paints the picture.

From The Hustle.

Luckily, I’ve never really experienced any of this. I’ve just had some bosses who had no ability to build connections with employees. It just felt like they were kind of…there. They didn’t light anyone up and it felt like they were easily replaceable.

I’ve learned how to lead from the great bosses I’ve had. While I’ve never hired anyone, I use their lessons on a weekly basis with my team and community. I still remember how they made me feel.

The way things are going, I’ll never have another boss in my lifetime. But I’m quite pleased with my track record.

I’ll end this with a statistic.

Of the highest performing and most fulfilled people in the workforce, 91% of them answered “Yes” to this question:

Do you feel like your boss cares about you as a person?

Slowing things down

A party of friends giving a cheers with their champagne glasses

As 2021 comes to a close, I’ve been intentionally taking my foot off the gas.

Scheduling fewer calls, not doing any outreach for the business, and having more days where nothing is scheduled.

It’s been tough, to say the least.

It has exposed the fact that I’m a workaholic. I don’t work 12-hour days or anything like that…but I like to feel productive on a daily basis.

But now that I’ve been learning how to slow down, I’m terrified.

Terrified that I’ll want things to stay like this. The fear is that I’ll never step on the gas again.

We hosted a Christmas party on Friday and it was amazing. All my local friends, pizza and sweets, hilarious games, everybody gone by midnight, no cleanup…perfection.

I figured I’d be hungover on Saturday so I did something I haven’t done in months.

I didn’t schedule anything.

Usually, this gives me anxiety. I never know if I’m doing the “right” thing. Or what to do at all.

But that morning (and afternoon), I laid on my couch with a smile as I watched YouTube videos and played chess. Nothing to do. Nowhere to be.

It wasn’t so scary after all.

But my possibly irrational fear is that I’ll want every day to be like this. This feels funny to type out because I’m sitting at my desk on a Monday morning preparing to write my book for three hours and then go to the gym.

I don’t want to do it all the time, but I like working my ass off. Not because it gives me a sense of self-worth but because I find it fun.

So the question moving forward, after the holidays, becomes:

How can I harmonize working hard and slowing down?

As I figure this out, I’ll let you know.

I deleted email from my phone

A person deleting the email app from their phone

Last year, like many during the pandemic, I became even more addicted to social media.

After reading Digital Minimalism by Cal Newport and watching The Social Dilemma, I deleted my Instagram—which up until that point was my favorite.

My fears were that I would become disconnected from my circles, that I wouldn’t be able to share my funny ideas, and that my creations wouldn’t get noticed.

After two days, I was stunned to find I was still alive.

Not only that, but I felt like I was thriving. My mind felt decluttered. I had no choice but to only focus on the actual world around me.

I won’t drone on about the pros and cons of social media and modern technology. Instead, I’d like to briefly discuss how my phone addiction manifested itself in my life once again.

Email.

Over the past year, I’ve grown my own business. It’s been one of the most challenging and rewarding things I’ve ever done (and continue to do). But along with such a feat have come all the usual entrepreneurial tropes.

Workaholism. Burnout. Being glued to my phone.

Today’s blog is about that last one. After quitting Instagram, it felt like there was an energy that needed to be exerted. For several months, I would let this energy out by reading, playing chess, or talking to a friend.

But once my business became even a tiny bit established, I found myself checking email and Facebook Messenger every three minutes or so.

I would check Gmail between every set at the gym. It was like opening the fridge to see if there’s any food moments after we just did that same thing.

The more successful I became, the more entrenched in these apps I felt. Until last week, I had to ask myself a question.

“Why do you absolutely need to check your email?”

Not want. Not feel strongly that you should. NEED.

100% of the time, the answer has been the same: I don’t.

So as the title of this blog states, I deleted Gmail from my phone.

Lo and behold, the world seems to be running fine. I have all my limbs and my friends are still alive.

I now check my email once (sometimes twice) a day on my computer. There have been zero fires to put out and not a single person has noticed.

The caveat here is that I work for myself and people are rarely relying on me to respond to them quickly. But I challenge anyone to set up a two-check boundary for email and see if anyone actually notices.

I look to Tim Ferriss’s quote:

“Email is a very convenient way of simulating forward motion without actually accomplishing anything.”

The next time we rush to check {insert favorite app here}, it may help to ask these questions first:

  1. Do I absolutely need to check this right now?
  2. What specifically am I trying to accomplish by checking this? (i.e. Am I just looking for an easy distraction?)
  3. What if this can wait?

To many, this may sound elementary. But these last few days without having something to compulsively check have felt euphoric.

It’s been the mind-equivalent to selling half my stuff and decluttering my home.

Work music

I love working to lo-fi, classical music, and videogame scores.

If you enjoy the same while doing deep work—writing, designing, editing—here’s a playlist I made for such occasions.

A day in the life of a Life Coach

Kinda creepy, eh?

I don’t find myself to be some high-performing productivity God.

But I do manage my time well and seem to get everything that I want to get done, done. Always productive; never busy.

People often say to me, “I’m sure you’re so busy…” But that’s not true. To me, busy implies a sense of being out of control—too many things to do and barely enough time to do them.

I have a ton of free time because I make sure that I do. I spend time with my friends and family. I take at least one trip each month. I play chess every day. I get plenty of sleep. (*The caveat here is that I’m 27, single, and I don’t have children.)

This is all on purpose. Whenever I feel any of these things begin to slip, I know it’s time to readjust my work and task load.

So today I thought I’d give a peek behind the curtain and run through an average workday for me. I hope it’s not as boring as I imagine it will be.

But here goes…

Between 5-6am: Wake up.

This was 6-7am before the time change this week. I’ve just kept the same circadian rhythm so now I can sound like one of those guys from an entrepreneur inspirational video.

I turn my SleepCycle alarm off. My phone is on airplane mode from the night before and I can’t take it off until I finish my morning routine.

I put my glasses on, make my bed, and go out to the kitchen to drink my fluids. In the fridge are my water bottles, ice-cold from the night before.

If I worked out the day prior, I chug a bottle of Athletic Greens. Then I drink half of my Nalgene of regular water.

I do this before any caffeine to make sure the first thing I do each day is hydrate after 8-10 hours of no water. Then I make a cup of coffee, usually Bulletproof.

6-8am: Morning routine.

I bring my coffee into my office, turn the lights and my computer on, and scratch off the day before on my giant wall calendar. Then I begin the morning routine I’ve basically had for the last two years.

  1. Look at my Google Calendar and block out my day in my notebook.
30-minute chunks.

2. Write my three affirmations:

I, Dillan Taylor, support myself as a prosperous coach.
I make $10K/mo.
I love doing scary things.

3. Read for 20-45 minutes.

Usually nonfiction to get the brain moving and pondering at the start of the day.

4. Write this blog.

Depending on the content and on my level of motivation, this can take anywhere from five minutes to an hour. If I love it, I post it to Facebook.

5. Solve 15 chess puzzles on chess.com.

I get 15 each day with my membership. So I go until they run out.

6. Stretch for 3-5 minutes.

Usually to a personal development or educational YouTube video.

These are mostly leg, back, and hip stretches…to prepare for a day of mostly sitting.

7. Meditate for 10 minutes.

I use the Waking Up app.

Meditation is the most important step of all…and it’s the easiest to skip.

8. Take my phone off airplane mode, maybe shower, and start my day.

The first two hours of the day are mine. Nothing to respond to. Nothing to solve or fix.

8-11am: Coaching sessions.

I try to get my sessions done earlier in the day when I have the most brainpower.

Active listening, reflecting, and challenging people and their thoughts can be mentally draining. If I can avoid sessions later in the day, I do.

11am-12pm: Eat and shower (if I haven’t already).

This is my breakfast, so to speak (type?). Usually eggs, sausage or bacon, and fruit (with peanut butter).

12-3pm: Other calls and miscellanous work.

These could be coaching sessions, connect calls, and admin stuff I didn’t finish on Monday.

If there’s space between tasks, I’ll read, go for a walk, or watch a few YouTube videos.

3-5pm: Gym.

At least three times per week. I use Fitbod to pick and track my workouts.

My weightlifting cycle is: push (chest/triceps), core (abs), pull (back and biceps), legs.

5-9pm: Dinner, maybe chill with friends.

If I’m in by myself for the night, I’ll cook something simple—usually a protein, veggie, and starch.

If I hang with friends, we may order food—usually Chipotle—or one of us will cook for the group. Wine or beer may be included.

In a perfect world, I wind down around 8:30pm. I use Freedom to block internet on my phone so I can’t stay up watching YouTube. I turn airplane mode on and stretch before getting into bed.

9pm: In bed.

If I’m still fairly awake, I read my Kindle until my body tells me it’s time to shut down.

I set my alarm for the morning, put my sleep mask on, and try to fall asleep.

10pm: Asleep.

Hopefully.

Repeat.

Waking up at 5am

A woman sleeping next to her alarm clock

This Sunday, the clocks moved back an hour. That extra hour of sleep was delicious.

Except I didn’t get a bonus hour. My circadian rhythm has stayed the same.

My previous sleep schedule: In bed at 10pm; Awake between 6-7am.

Now that time has been pushed back, I’ve been going to bed at 9pm and waking up between 5-6am.

All the cliches of waking up early AF are true.

  1. My days feel more productive.
  2. It’s therapeudic to feel like I’m the only one awake in the world.
  3. I love experiencing the sunrise.
  4. It feels like I get to do more in a day.

I feel bad for people who despise the morning time.

The downside is that I get exhausted around 8:30pm. Not ideal for nightlife. That’s okay.

Sacrifices need to be made in order for us to feel more whole.

This is a sacrifice I’m willing to make.

My work playlist

When I’m working, studying, or reading, here’s my playlist I listen to.

It’s perfect for deep work and getting in the zone.

3 rules for disagreeing with someone

In the past four years, I’ve had debates, discourse, and disagreements about politics, feminism, religion, race, transgenderism, vaccines, and more.

Some were heated and aggressive. Some were fun and fruitful.

I handled myself quite well during some. I sounded like an ass during others.

It doesn’t matter how much we connect or get along with someone else. We’ll never agree with 100% of what they believe. Disagreeing is a natural part of the human experience.

Through my conversational struggles and from the many mistakes I’ve made, I’ve learned three helpful (yet difficult) rules for having more productive disagreements.

Feel free to disagree with them (get it?).

1) Come to terms with this truth: We can never force someone to think, feel, or believe something. They have to get there on their own.

We are not creatures of logic. We make decisions based on emotion and then justify those decisions with logic.

In countless disagreements, I foolishly thought that if I just brought up another point of juicy rationale, I’d crack the other person and they’d see things the way I saw them.

Confirmation bias plagues us all. It will always be easy for us to pick and choose the (supposed) evidence which fits our narrative. We decide what we want to be true and identify with that belief. Then, if someone disagrees with that belief, it feels like they’re disagreeing with who we are as a person.

Yesterday, my friend told me about a heated debate between his two friends regarding the COVID vaccine.

One friend was arguing that the vaccines are probably not safe. He sent a screenshot of a well-sourced article listing the possible negative side effects.

The other friend then went to that same article and screenshotted a paragraph that was conveniently left out: the conclusion which said that the vaccine was ultimately proven to be safe.

I heard this part and thought that would be the shutting of the door to their argument. But the friend merely brushed it off and continued with his disputes.

With the power of the internet, we can find millions of people who agree with every possible opinion known to man. There are people with PhDs who believe the earth is flat. There are intelligent people who think the planet is 6000 years old.

Whether it’s opinions about vaccines or about our favorite athletes…our default is to cling to evidence that supports how we already feel and to shy away from evidence that challenges our beliefs.

Since that’s the case, we cannot ‘logic’ our way through a disagreement.

2) Ask way more questions.

There are several reasons for this.

Firstly, it’s crucial to understand fully what we’re arguing against. The last thing we want to do is misrepresent someone and challenge ideas they don’t actually hold.

We ask questions to paint a crystal clear picture of what they’re actually thinking.

A strawman is a fallacy in which we argue against the worst possible representation of someone’s point.

Example: “Oh, we need to do something about climate change? So you just want us to stop driving cars and stop having kids, huh?”

No…that’s not what they’re saying. That’s a strawman.

By asking curious and clarifying questions (not leading questions meant to achieve a ‘gotcha’ moment), we’re able to steelman. This is the opposite of a strawman, in which we’re able to articulate someone’s opinions perfectly.

A steelman would have us say: “So just to be clear, you believe…” Then they would say: “Yes.”

That has to be our starting point.

The second reason asking questions is so effective is it demonstrates to the other person that we’re not here to attack them. The more curious we are, the more we show we just want to understand them, the more their guard will drop.

This isn’t a trick. We want everyone involved to lower their guard and feel safe to express themselves without reacting in a defensive manner.

Curious questions make it a conversation, not a debate. This is ideal. Debates have winners and losers. But in great conversations, everybody wins.

The final benefit of asking questions is it adds scrutiny to the conversation, exposing the true strength of the person’s argument.

While this should never be the goal of asking questions, it’s possible that the person “defeats” themselves with their own words. It’s a great way to see if this person has given thought and research into this thing they believe or if they just want to believe this thing.

I recently had a disagreement over the COVID vaccines myself. (To be clear, I’m not super passionate about vaccines. It’s just come up a ton in recent months so it’s fresh on my mind.)

My friend who was super wary of the vaccines was sharing his opinions. I did my best to just ask questions. As I did, I felt that their answers were on shaky ground and I found many holes in their arguments.

There were a lot of “I don’t know’s” and “I don’t remember’s.”

Again, I wasn’t trying to slam dunk this person I have a ton of love for. I just wanted to get a clear picture of their beliefs.

Asking questions is hard, especially when we don’t feel curious at all. Curiosity is tough to fake. But it’s the only way to ensure nothing gets lost in translation.

3) Separate the person from the argument.

We’re not arguing with people; we’re arguing with ideas.

I could go on for hours about how much I hated having Donald Trump as our president. But I’m also super close with people who absolutely loved him.

That doesn’t mean I actually hate these people. It just means I don’t connect with their ideas. We don’t need to agree with someone to hug them or to have a beer with them.

So in a disagreement, it’s powerful to avoid saying things like:

• “Where you’re wrong is…”
• “What you don’t see is…”
• “I disagree with you on…”

With phrases like these, it sounds again like we’re disagreeing with them as a person.

It’s better to say things like:

• “My problem with that perspective is…”
• “That argument to me is…”
• “The way I see things is…”

With phrases like these, we make it apparent that we’re just discussing ideas. It’s not a battle over who’s more righteous, more intelligent, or more sophisticated.

Conclusion

We have to pick our battles. I’ve ruined social events because I thought it was the perfect time to argue against Catholicism.

But we should also feel safe and free enough to express ourselves. This can best be done if we change our goals for disagreement.

Instead of wanting to win, we should want to collaborate and learn.

“Seek out people, books or ideas that contradict your current beliefs and one of two things will happen…A) you will discover that you are wrong or B) you will improve your arguments for your own ideas.”

-Mark Manson

Simple lesson (pt. 2)

A simple lesson I learned this year:

“Working harder” is almost never the solution. Nine times out of ten, it’s more effective and peaceful to cut out all the nonessentials first.

Actually do stuff

A guy surfing on a huge wave
Photo by: Surf Gear Ltd.

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.

An extra hour of sleep

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.

Dying to get back

I went on a lovely family vacation this weekend. Dad’s lake house. Thursday to Sunday.

We went tubing, boating, and swimming every day. I ate garbage and slept in a bunk bed.

One of my favorite parts of taking breaks like this is that I’m always itching to return to my space and routine.

It’s Monday, my favorite day of the week…and I sit here with a smile on my face.

How I maintain my energy

A pile of double A batteries

On a coaching mastermind call yesterday, we discussed ways we stay energized.

For me, it’s three things.

1) When I’m in a rut, I check my health trifecta.

• Am I getting at least seven hours of sleep each night?
• Am I eating a lot of processed foods and sugar?
• Have I exercised at least three times this week?

2) I take one weekend off each month.

I happily work on weekends since that’s when many of my clients are available. But once a month, I take a long week or weekend off to travel somewhere (usually on the east coast).

It’s a refreshing break after three weeks of hard work and I always return home feeling amped to get back to my routine and do it all over again.

Since I have no kids or other major responsibilities at this time, I figure I should take advantage of it while I can.

3) I spend a lot of time doing things I enjoy.

Chess, martial arts, exercise, quality time with friends, reading…

I find it vital to our souls to spend a good amount of time away from anything having to do with work or money. Like a vacation, it makes us appreciate our time back even more.

We should all have a thing. Preferably something challenging—a skill or a craft—we can practice and get better at.

For me, these three things are perfect substitutes for any drug or stimulant.

Sleeping in

A baby sleeping
Me at age 7.

I hate sleeping in.

When I’m up, I’m up. Sometimes it’s a nuisance but I’m mostly grateful.

I like hopping right out of bed and starting my day.

Perhaps this was born out of necessity since I don’t use my phone for the first two hours of the morning.

I’m of the opinion that extra sleep is best gained by going to bed earlier.

But what do I know? I’m just a guy typing on his keyboard at 6:30 in the morning.

How you do one thing

I’ve found that when one area of my life begins to slip, so too do other areas.

When I skip on a bunch of exercises in a week, it tends to be an unproductive week of work as well.

When I have an unproductive week of work, I feel less secure in my friendships.

When I feel less secure in my friendships, it’s harder for me to cook healthy meals.

The opposite is also true. When one thing is going super well, other facets of my life seem to thrive.

“How you do one thing is how you do everything.”

You don’t need

You don’t need a better computer to become a writer.
You don’t need a better guitar to become a musician.
You don’t need a better camera to become a photographer.
What you need is to get to work.

James Clear

What’s your system?

A bunch of electronic chords plugged into a system
The inside of my brain.

We all have a system for doing things.

Some of us reject the the word system. That’s fine, but we all have a series of actions we take or don’t take with everything we do. Habits are just a form of systems.

“You do not rise to the level of your goals. You fall to the level of your systems.”
― James Clear, Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones

Our bank accounts are the sum total of our financial habits. The way we look and feel is the sum total of our diet and exercise habits. How messy or tidy our space is is the sum total of our cleanliness habits.

Last month, I got terrible sleep. Since my sleep quality is the sum total of my sleeping habits, I did some investigation.

I noticed I was:

• on my phone a lot right before bed
• eating later in the day
• drinking more alcohol than usual

So I improved the system. No phone after 10pm. Not eating past 8pm. No alcohol on weekdays.

After just one week, my sleep quality has improved drastically and I feel ten times more refreshed and energetic.

Dillan Taylor's sleep report
My sleep data from Sleep Cycle.

In a recent conversation with a coaching friend, she told me, “It’s impressive to me how you set a goal and just attack it.” I was truly touched by her compliment, but right away I explained that that’s not how I approach things.

In the self-help world, we’re told to set SMART goals. Specific, Measurable, Achievable, Realistic, Timely.
e.g. “I’m going to lose 15 pounds by August 2nd.”

I understand the utility of setting such specific goals, but they don’t light me up at all. I usually change my mind halfway through working toward them or if I do accomplish them, I’m left with this empty feeling and simply ask, “Now what?”

I much prefer systems.

To be more clear: I prefer designing systems which allow me to consistently doing the things I enjoy and get better at them. Here are a few of them…

Coaching:

I reach out to a certain number of people each week and update my client notes every Monday. I’m not working toward a defined number of clients or a specific dollar amount. I just love coaching and growing my business, so I have a system in place which lets me do those things well every single week.

Exercise:

I’ve never set an exercise goal. I couldn’t care less about how much I can bench or squat. But I love exercise, so I make sure I go to the gym three to four times each week. The cycle: push muscles (chest and triceps), core, pull muscles (back and biceps), and legs.

This blog:

I look at the analytics of this blog about once a year. I’m eternally grateful for how the number of readers has increased, but I don’t do it to raise traffic. I write this blog each morning because it helps me shape and get clarity on my thoughts on things. I’ve become more articulate and I get to share stories and ideas with friends and people outside my circle. So I’ve made it part of my morning routine.

Conclusion

So I’ll ask you: How can you create a system for the things you enjoy so you can do them more and do them better?

Do you reject systems? If so, why? And does rejecting systems lead you to take more action or less?

Write like a motherfucker

A person writing with pen and paper

Last night, I finished another chapter of Cheryl Strayed’s Tiny Beautiful Things. It was my favorite one yet.

The book consists of captivating Dear Sugar columns; people write in asking for her advice and she tells gripping, emotional stories and gives life-changing insights.

The chapter I read before bed last night was called “Write Like a Motherfucker.” In it, a woman wrote in looking for much needed motivation. She’s a writer who doesn’t write. She’s often paralyzed by her depression.

She writes:

“I’m…a high-functioning head case, one who jokes enough that most people don’t know the truth. The truth: I am sick with panic that I cannot—will not —override my limitations, insecurities, jealousies, and ineptitude, to write well, with intelligence and heart and lengthiness. And I fear that even if I do manage to write, that the stories I write will be disregarded and mocked.”

What powerful vulnerability. And what a concrete example of someone who wants something but believes there’s something in the way.

To be clear, I am NOT downplaying the role of mental health here. I love that Cheryl opens by recommending professional help to this woman. The power of not having the energy to do what we want to do is stark.

But the reason I love this chapter so much is because Cheryl throws down some masterful tough love.

The phrase tough love often gets a bad rep. People tend to get distracted by the first part, tough: possibly unpleasant, firm, or uncomfortable…that they forget about the second part entirely, love: coming from a place of “I care about you and your wellbeing.”

I believe in accepting others for who they are and showing consistent compassion to ourselves and those around us. But I also believe in challenging ourselves and those around us for the sake of pushing humans to be better.

Cheryl hits her with this hammer:

“The most fascinating thing to me about your letter is that buried beneath all the anxiety and sorrow and fear and self-loathing, there’s arrogance at its core. It presumes you should be successful at twenty-six, when really it takes most writers so much longer to get there.”

Wow. No pity party here.

I can only imagine how much this stung to read. But Cheryl does a fantastic job in relating her own experiences and assuring her that this all comes from a place of love and care. Plus, the point is not: Does this sting? The point is: Is this true and is this useful?

Going through mental chaos is God damn difficult. In many cases, it can be debilitating. But unfortunately, that doesn’t remove the work that needs to be done.

Cheryl describes humility: not being up too high or down too low, but on the ground level. She writes:

“We get the work done on the ground level. And the kindest thing I can do for you is to tell you to get your ass on the floor. I know it’s hard to write, darling. But it’s harder not to. The only way you’ll find out if you “have it in you” is to get to work and see if you do. The only way to override your “limitations, insecurities, jealousies, and ineptitude” is to produce. You have limitations. You are in some ways inept. This is true of every writer, and it’s especially true of writers who are twenty-six. You will feel insecure and jealous. How much power you give those feelings is entirely up to you.”

The negative feelings we experience are absolutely valid. But the work still needs to be done. It’s up to us to continue to show up and do it.

“Writing is hard for every last one of us—straight white men included. Coal mining is harder. Do you think miners stand around all day talking about how hard it is to mine for coal? They do not. They simply dig…

You need to do the same, dear sweet arrogant beautiful crazy talented tortured rising star glowbug.

So write…Not like a girl. Not like a boy. Write like a motherfucker.”

(Strayed, Cheryl. Tiny Beautiful Things (p. 60). Knopf Doubleday Publishing Group. Kindle Edition.)

2nd vaccine

I got my second vaccine yesterday. I slept in an extra hour and a half this morning—something I never do.

My body aches and I’m exhausted. But I have a long day of work today so I won’t be taking it super easy.

As shitty as it feel physically, it feels nice to have habits and systems in place which help me take care of the things I want to get done.

One of my favorite phrases comes to mind today:

No hurry; no pause.

Meaning, I don’t have to rush anything, so long as I show up every day and do the work.