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  • Writer's pictureDillan Taylor

3 things I’ve learned after 1000 coaching sessions

The first coaching session I ever ran was on June 26, 2020. A friend agreed to be my first guinea pig.

I began coaching my buddies for free. Eventually, I charged $40 a call. Then $50. Then $80. Then I started offering 3-month packages instead of per-session prices.

In March of 2021, I joined the Insight Coaching Community (ICC). It was there that I would find my people, learn how to create clients, and build the career of my dreams.

Since then, I’ve:

  1. been hired as an ICC team member to train other coaches

  2. coached nearly 1000 hours

  3. had intense conversations with 100+ people

Last week, a woman shared with me my favorite description of a coach I’ve ever heard. She said, “I thought a life coach was just an unqualified therapist?”

After a good laugh, I explained the difference. In oversimplified terms, therapy tends to uncover the past; coaching is meant to create change for a better future.

While I certainly don’t claim to have any kind of psychological expertise, I’ve learned a ton about the mindsets and behaviors of human beings over the last two years.

Here are my top three insights.

1) We protect ourselves with our identities.

Every person on the planet has certain proclivities, personalities, and tendencies that set them apart. But we tend to think these are fixed.

People say things like:

  1. “I’m the kind of person who…”

  2. “That’s just not me.”

  3. “I could never…”

We craft these identities for ourselves. That way, when something undesirable happens to us we can simply blame our identity.

If our business isn’t doing well, we can point to the fact that we’re just not a pushy or organized person. That explains it. It’s not that we’re not doing the work; it’s our timid, non-masculine identity’s fault. It’s just who we are.

But these aren’t definitions; they’re stories.

“I’m not a go-getter,” is really: “The story I’ve lived in the past has not been one who follows through with what they want.”

This is good news. Because as cheesy as it sounds, we can change the story. How do I know?

Because I’ve seen people alter their stories right before my eyes. I’ve seen…

  1. perfectionists become pragmatists

  2. people pleasers set hard boundaries

  3. go with the flow types create organized systems

  4. impulsive actors become proactive

  5. hyper-achievers embrace acceptance and gratitude

Most of the people I work with have turned into completely different humans in a matter of months. That’s not an advertisement for my services and it’s certainly not a guarantee. It just highlights a simple process that something like coaching can provide.

Step 1: Act and think a certain way.

Step 2: Open up about what you actually want and what you think is in the way of that. Notice how far your desires are from your current life.

Step 3: Pinpoint which obstacles are real and which are only in your head (most of them are just imagined—e.g. fears, doubts, uncertainties).

Step 4: Accept that if you keep doing exactly what you’re doing, you’ll keep getting exactly what you’ve been getting. Start taking action and making changes that make you feel uncomfortable and stretch you. Gather insights from failures and celebrate wins.

Step 5: Act and think in new ways.

Step 6: Repeat.

That sounds like every self-improvement book ever written. But that’s because it’s impossible not to improve oneself by following this stupidly-simplified formula.

Unfortunately, most people stop at step 1. They go through life without challenging their modes of operation. But all it takes is one person to ask one question for us to stop looking at the world through a toilet paper roll.

And in my experience, it’s those who are not invested in their identities who see the quickest results…because they have no excuses.

2) People want answers but need insight.

For context, Webster defines insight as: “gaining a more accurate or deeper understanding of something.”

My mentor shares two truths when it comes to the coaching world:

  1. People don’t do well with solutions they’ve had little to no part in creating.

  2. Our insights will never be as powerful as their insights, even if they’re the same.

Holding space for someone is one of the most powerful and valuable things we can do for them.

We often jump right into problem-solving and we miss what’s really going on. This usually shows up in three main ways:

  1. We believe them when they tell us what they’re struggling with when really there’s a much deeper problem.

  2. We offer advice and suggestions when all they want right now is to be heard and understood.

  3. We think our words are more useful than their thoughts and we limit their ability to gather insight on their own.

Here are some examples for each.

1. Not believing the first problem:

I coached a guy once who opened the call by saying, “I’ve done a lot this year already. I want to define what my next big projects and achievements are.”

“Great,” I said. “How much more doing and achieving would you need to feel satisfied?”

It was the fastest turn of events in a session I had ever seen. He started laughing.

“Wow,” he chuckled. “I have so much on my plate right now. I have no idea why I thought adding more to it would make me more fulfilled. It would crush me. I’m already overwhelmed.”

So we spent the rest of the call discussing his obsession with taking action at the expense of his mental sanity. That was the problem beneath the problem.

Notice how I slightly disregarded his original statement. He declared he wanted to brainstorm his next actions. If I just went along with that and we started spitballing, we never would’ve touched on the root of the issue.

2. On holding space:

At the end of each coaching session, I ask the client what they got out of our conversation. The most common response?

“I just feel ten times better saying all this stuff out loud.”

This is the same reason journaling is so therapeutic. When we take the thoughts out of our brains and put them into the world where they can be seen or heard, they become more real and less daunting.

In the coaching sphere, there’s a concept called the lamp post theory. It says that even talking to a lamp post about your fears and accomplishments would improve a person’s life.

Now imagine instead of a lamp post there’s another human being reflecting your words back to you, asking you thought-provoking questions, and challenging your answers.

3. Curiosity before solutions.

It’s the #1 principle in my business.

I mentioned earlier that feeding someone an answer will never be as impactful as them finding that answer on their own. There is the rare case where someone asks us for our thoughts and actually uses our suggestions, but those instances are far and few between.

A few months ago, I was coaching a woman for the first time. She was having trouble setting boundaries with her hometown friends. She felt less connected to them and didn’t enjoy going out, drinking, and doing drugs all the time.

It would’ve been so easy for me to tell her what she was doing and why it wasn’t working. But I just asked her questions.

How is pleasing these people serving you? How is it hurting you? If nothing changed, what would you feel like a year from now? What are you responsible for? What’s outside of your control here?

After 50 minutes, she had an insight.

“Oh my God,” she laughed. “I don’t know why, but I feel responsible for their emotions. Like, how important do I think I am that their happiness starts and stops with me?” She started making fun of herself.

She asked me why it took her an hour to realize she wasn’t in charge of other people’s wellbeing. And that’s how insight works.

We can’t force anyone to think, do, or feel anything. It has to come from them first. And while there’s no guarantee, we can increase the likelihood of insight by being wildly curious and holding up a mirror for them.

I’ve had plenty of sessions where I ask piercing questions, reflect their words back to them, and challenge their thinking…and they feel nothing. That’s okay.

It’s not my job to ensure an insight. That’d be like a gym guaranteeing you a great body. You have to show up consistently and do the work.

We can only make changes when an insight is had. But most people want the change before the insight.

3) We’re all the same.

I’ve worked with: software engineers, CEOs, comedians, coaches, politicians, content creators, writers, doctors, athletes, marines, financial advisors, tutors, musicians, dog-walkers, yoga instructors, sales reps, and more.

And they’re all the same. Here why.

There’s a basic human trend I’ve noticed.

  1. We all want stuff—usually changes in our outcomes, mindsets, or situations.

  2. We feel like something’s in the way—usually fear, doubt, or uncertainty.

  3. We either work actively to maneuver through these challenges or we let them keep us where we are.

This trend is true of every single person I’ve coached regardless of how much money they make, what their personality is like, or how big or small their goals are. It’s true for me. It’s true for all of us.

I could ask you right now: What do you want most right now that you don’t have? What do you think is in the way?

A past client who was making $200k+/year had purchased her dream car and dream house. It didn’t bring her any of the fulfillment she was expecting, so we spent months diving into the things that did.

Another client wanted to get better at receiving criticism, so we did an exercise where he reached out to all his friends and coworkers and asked for open and honest feedback.

We’re all the same. We want things and we think something’s in the way. Then we either do something about it or we don’t.

Coaching helps those who do want to do something about it.

In summary

  1. We craft identities for ourselves to excuse the things that don’t go our way.

  2. We want people to give us answers when we really need to create our own.

  3. We all want things in life and think there are obstacles keeping us from getting them.

This is my dream job. I get paid to help others build the lives they truly want to live. It’s rewarding and fulfilling at the highest level.

It also holds up the mirror to me and my own ways of doing/thinking. I gather insights as I see my clients gather insights. I get inspired. Sometimes I get teary-eyed or get chills listening to what my clients are feeling and accomplishing.

These first 1000 sessions have been a tremendous learning experience. And this unqualified therapist couldn’t be more excited for the next 1000.


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