My Experience Working With a Life Coach

I hired a “life coach” two years ago.

This unexpected investment has undoubtedly been the best decision I have ever made for my personal growth. I feel exponentially more confident in the major areas of my life including my career, health, romantic relationships.

It felt embarrassing to admit because life coaches are notorious for being scam artists. I’d imagine themselves posting motivational quotes on Instagram and not even having their life in order. I also felt weird to share this because hiring a life coach must mean that I wasn’t in a good place in my life, which may have been true, but that’s something you don’t brag about on a first date.

Why did I hire a life coach?
How did I choose who to work with?
How did this experience help me level up my life?
Why didn’t I work with a therapist?
How much does life coaching cost?
What lessons did I learn?

These are all the questions (and more) that I hope to unpack in this piece. I’m writing this (1) to help people who are curious about life coaching for themselves and (2) it got really annoying to repeat myself to every semi-ambitious person who wants to improve their life through professional coaching. So viola — a Medium post — the novelty!

Below is my unique experience. I have no idea how other life coaches operate or what their style is. But I hope that this piece can give you more data points on whether or not life coaching is right for you. Enjoy.

How I Met My Life Coach

Charlie Taibi, the founder of an educational program for young adults called Year On, invited me to a dinner for folks interested in improving education. I spent the last few years writing articles/books and mentoring students about learning important skills outside of the classroom. This dinner was a “hell-yes.”

I walked into a large group of 10 people or so. I personally hate dinners more than 6 people because it’s hard to have one conversation together… and when you break out into mini groups, you don’t get a chance to meet others. My strategy with large dinners is to sit on the far end of the table. I would rather have 1 deep conversation with the person in front of me vs 3 scattered conversations if I sat in the middle.

This is where I first met Kat Koh, who I would have no idea would change my life. I asked her how she knew Charlie and Kat told me she worked part-time as a mentor for Year On students. She also served as the community manager for Seth Godin’s AltMBA program. That’s pretty dope. I’ve mentored students at Year On as well and I love Seth Godin’s work, especially his AltMBA program that I’ve considered joining myself.

We chatted more about our experiences in education and discovered writers that we both admired like Chris Guillebeau, Emily Smith, and Brene Brown. Kat instantly impressed me at her knowledge of business and personal development. I got the impression that this person has spent a ton of time in understanding herself and making her life fucking awesome.

I forgot how things went down but I must have asked her, “Are your biggest focuses on Year On and AltMBA?” This is when she revealed that the 3rd part of her work was serving as a career coach for creative people.

“Wait, what? What do you do?”

Kat went on to describe how she helped artists, writers, and creative people do their best work. She shared how most of the problems she helps her clients weren’t necessarily always “career” related but addressed general approaches to their lives that are stopping them from doing their best work. I replied, “OK… so like a life coach?”

My mind exploded. What in the world?

Kat is a life coach!? Every single life coach that I’ve met in the past are usually some spiritual guru or a blogger who has too many photos of themselves on their social media. Never have I seen a “life coach” who actually understands startups, education, and the writers that I admire.

Very interesting…

We added each other on Facebook and didn’t chat much after dinner. I felt like the next month was slowly processing my assumptions of what a life coach is. Whatever. It wasn’t relevant to me (or so I thought). My life is pretty chill. I have a great job, cool friends, and time to explore things that I’m curious about. But there was one part of my life that I was deeply insecure about: my body.

I wasn’t “fat” but I was ultimately not proud of how I looked. What I was most ashamed of was my disgusting eating habits and failures to stick with any workout plan I’ve tried.

In 8th grade, I tried P90x for the first time and was inspired by the “Before and After” videos in the advertisements. So I got my dad’s mini camera to take photos of me shirtless as a “before” story so that after 90 days, I will take my “after” photos and be so proud of myself. I made a short video of these photos along with a vlog (before it was cool) about my challenge and posted it on YouTube. I did the P90x workouts every day for two weeks and stopped because it got too difficult or “life” got in the way.

People at school asked about how I was doing and I have never felt so much shame to admit that I wasn’t going through with it anymore. A month later, my friend threw a birthday party and for a prank, someone turned off all the lights in the bedroom, four friends pinned me down on the ground, and everyone watched my P90x vlog video on the desktop computer where the room erupted in laughter when they saw my shirtless pictures. I brushed it off but when I walked back home, I locked my room, removed the P90x video from YouTube, and cried so much that my pillow case was completely soaked.

In high school, I used to eat Taco Bell multiple times a week (not exaggerating). I have tried everything on their menu. Taco Bell was life.

I tried a No Taco Bell challenge for a month. I remember telling my high school best friend about it feeling super pumped. Avoided crunchy tacos for 2 weeks before giving in and waiting in that familiar drive-thru line. I’ve tried this challenge at least 10 different times in my life and failed every single one. My best friend supported me in the beginning but wasn’t surprised by the 4th or 5th time when I texted her a picture of me and a Chicken Quesadilla at 11 pm on a Friday night. I couldn’t help myself.

My life’s diet consisted of Taco Bell, KFC, Pizza Hut, milk tea, rice, spam, ramen, and every popular junk food imaginable. Lucky for me, I loved playing sports so it is very normal to eat a Crunch Wrap Supreme and down a Baja Blast minutes before playing two hours of basketball. Everything canceled out, especially when you’re a young teenager.

But I knew that this wasn’t healthy. I wanted to feel confident to take off my shirt at the beach. I desperately wanted 6-pack abs. I need to change.

So who do I go? A personal trainer? A Nutritionist? A coach?

I remember Kat was a coach. But she told me she was a career coach so she couldn’t be the right person to help me. But maybe she knows someone who can?

I sent her this message.

I didn’t really know that I wanted. But this message was the current mental model of what I thought a life coach should be: Another version of Tam, except 10 years wiser and buff.

After Kat told me her friends were all booked up, she offered to coach me herself. I could imagine working with someone like her but thought her website says she “help creatives get unstuck” which wasn’t my situation.

The skeptic in me thought: What a sneaky little marketer… conveniently switching her value proposition when the opportunity presented itself. But wait… I actually like Kat a lot. She’s either a charming con-artist or a legit coach who can solve my problem.

I gave her the benefit of the doubt and booked a session for the following week.

Our first session

I had no idea what to expect. My only definition of a coach was my old basketball coaches sitting on the sideline directing the plays. I felt nervous. I thought Kat was cool but am I really ready to open up to someone I just met?

Kat greeted me as I walked into her side project at the time: a co-working/co-living space she ran with her friend. (So co-ol). We went upstairs and had a bit of small talk before officially starting the session. Kat’s presence felt friendly and warm.

She thanked me for reaching out and asked what my goals were. I told her about my failures to stick to a workout plan or have a healthy diet. How much it sucked all my life to be in confident in many other parts of my life except my body. If there was a ratio of how much I talked vs how much Kat talked, it would be a 80/20 split.

We dug deeper into what I have tried before where I shared how I failed P90x, Taco Bell challenge, and several other diets I’ve tried. I don’t remember the exact wording but within 30 minutes, she helped me see a pattern: I get off to a really good start to the plan that I commit to… but once I miss a day or two, I quit and deem myself a failure.

I thought, lol. That is so obvious.

She asked me, “Knowing this, what do you think you want to do differently going forward?”

“Well, I don’t know Kat… maybe go slower?”

She smiled. Fucking Kat…

We spent the last half of the session going over what that might look like. By the end, I had a rough plan of what I would do to build sustainable habits around exercise and nutrition. My only goal was to eat 1 healthy meal a day. No need to work out. I could freely eat fast food on the other meals. I could work out if I wanted to. But I had to simply eat 1 healthy meal a day no matter what. Everything else is extra.

In retrospect, this is very simple to figure out but at that time, this felt like a huge breakthrough for me. For an ambitious person who likes results fast, this taught me that I need to be patient and focus on habits/systems vs. going at things with brute force.

At the end of the session, Kat told me that she’s happy to work with me towards this goal and before she can finish her sentence, I said fuck yes. Where do I sign up?

Working with a life coach was expensive. I paid $750 a month to meet with her 3 times a month with unlimited text/email support. But at that stage of my life, I would pay any amount of money to help me get healthy.

The first 6 months

I actually had no idea what I signed up for. All I knew is that I had a problem and I was willing to do anything to solve it.

I didn’t understand at the time that a coach doesn’t have to be a nutritionist to help you change your habits. A coach digs deep to discover the root cause of why you overeat and creating solutions that best work for you.

Well, why did I eat out so often? Simple. I never cooked a single meal in life, excluding cereal and ramen. The first 6 months forced me to learn what foods are healthy. I asked my friends how to peel a potato and how to cut an avocado. Cooking felt so foreign to me. But every meal I made for myself was the biggest win of my week. I would text Kat several photos of these small wins.

We started off at 1 healthy meal a day. After I found success for a few weeks, I bumped it up to 2 healthy meals a day. Then added on 1 workout a week. Then 2 workouts a week.

I had some slip ups along the way. I brought them up to Kat and she had no judgment on them. She actually encouraged slip-ups and celebrated it.

“Isn’t it bad that I’m not hitting the goal every single day?”

This is when she taught me something that I love: It’s not about the number of times you fall off the wagon. What’s more important is how fast you get back on the wagon.

When I did P90X, I got off the wagon after 2 weeks and never went back on. Instead, this approach says, It’s OK to miss a day. Just so long as your time to get back on is quick. This was the main reason why this workout/eating plan finally worked.

I slowly started to enjoy cooking. Every time I ate fast food again, I could literally feel my body becoming sluggish and uneasy.

I have had friends act as accountability buddies in the past but this was way different because (1) I was paying money for this. It would be embarrassing for me to invest so much of my income and then come to our session admitting that I missed the entire week. (2) Kat was my friend but more importantly, she was my coach. She’s not sharing anything about her life (unless I explicitly asked) like an accountability buddy would. The focus is entirely on me and the frameworks/motivational interviewing was the bulk of our sessions to make this plan sustainable.

I could not recognize myself during this transformation. I quickly learned that yes, I could do this all on my own. Everything that I’m doing is not new. It’s not like the information is hidden on the internet. But a professional coach is someone who accelerates the growth.

Doing this all on my own has actually failed me more times than I’d like to admit. Maybe it was the money that I’m investing in. Maybe it was having someone be accountable and encouraging towards me. Maybe it’s all placebo.

But if something is working, I ain’t gonna change one bit.

From never using the stove top before to meal prepping for the first time is unimaginable for me. Holy shit.

Kat didn’t just motivate me to eat healthier. She has literally changed the habits that I never thought I could break. She taught me what sustainable change looks like and I could never be more grateful.

(Kat’s notes: Not true. You changed your habits. I supported you to see which ones you really wanted to change and get clear on the “how”. gain, you experienced what sustainable change looks like by… making changes sustainably yourself! Big difference :D)

The next 18 months

Here’s where things got even more interesting. I felt super solid with my nutrition/exercise routines. I wanted to explore other parts of my life that I felt like I could use more clarity and support.

This post is long enough so I’ll give some high-level topics that we covered:

My mental blocks and fears around dating
Whether to take a huge job promotion or keep doing my thing
What I really want in my career
What my north star is
How to best structure and use my time (and calendar)
What it means to live authentically
Why I’m afraid to go for the win and settle for a tie in competitions

Kat even helped me tame my monkey mind.

It’s not like I found out my life’s purpose after 1 session. Similar to how eating healthy took 6 months to get me in a place of confidence, many of these topics took several sessions to gain more clarity. I admit that some sessions weren’t incredibly valuable. It could have been my stubbornness to think that I already knew the answer, or me just not being in the correct emotional/mental space for the session. But for most sessions, I walk away with my mind racing with ideas and discovering significant breakthroughs about myself. I feel more confident that I’m understanding myself better which I believe is the most important skill you can have.

Before I make any big decision in my life or when I have many unknowns around something that is important to me, I turn to Kat for clarity.

Should you work with a life coach?

I believe you should work with a life coach if you want to accelerate your personal growth.

I have never worked with a therapist before but it seems like they are there to help you heal or look at unresolved traumas. Kat does not operate like this. I know there are some coaches who are a mix of coaching and therapy which may make more sense for you if you fall into this camp.

Arguably, you can improve your life all on your own. Arguably, you can learn almost anything on your own. You don’t need a physical trainer to help you do squats or deadlift. But you can imagine how much faster and stronger you will be if you hire professional help.

You can learn cooking from so many amazing videos on YouTube. But you can imagine how much more effective your learning will be if a chef taught you first hand.

So yes, you can go through life doing your own thing. The majority of people do. The freaks like myself who optimize for learning are usually the ones that are most drawn to life coaching.

I got lucky working with my life coach. I met one. I liked her. I worked with her.

It’s hard for me to give you advice on what coach to work with. I’m getting better at listening to my gut.

My values aligned with Kat. I liked her as a human. I had no idea about her competence in coaching. She actually went through some rigorous coaching program that I don’t know how legit it is. But after our first session, I was sold.

If you’re looking for potential coaches to work with, I recommend doing a single session with them to test them out. It would be best if a friend who has worked with them before telling you the low down of what to expect. Then listen to your gut on whether or not you think it’s a good fit. (Which I know can be horrible advice to some, like a younger version of myself, but it’s something that I’m trusting more vs a pros and cons list.)

Final thoughts

It has been two years since I met Kat and feel incredibly grateful for her help. I took a break from coaching to travel a bit but I always turn back to Kat for her guidance. I’m currently transitioning into a new job and have a few options on the table. The first person I reached out to was obviously her.

If you’ve worked with a life coach, I’m curious to hear about your experiences on what that was like for you. If you’re curious about my own life coach, you can check out her website here, although last time I talked to her, she’s completely booked for new clients.