Even Michael Jordan Had a Coach

The words made me stop cold in my tracks. I always had an answer. A comeback. But this time I knew she was right: her words meant I had to take action.

It was July 2014 — I was at a networking event in Boston and ended up having a conversation with someone who just made the jump to being a career/life coach.

I ended up sharing one of my dreams with her:

“I’m want to be a career coach one day. I’ve helped a lot of people land great jobs and figure out what they want to do. I love it.

What she said next scared me:

“You already are a coach, you just need to start doing it”

Damn. Now I had to do something.

I could tell you about taking massive action immediately after this conversation, but that’s not what happened. I was still scared. It took me several months to take action on this thing I knew I had to do. You know what held me back? Picking a name. At least that’s what I told myself. In reality, I was a bit scared of doing something out in the open.

What would people say?

Everyone has something that holds them back. For some, it is perfection — needing everything to be perfect. For others, it is creating such massive goals that they become overwhelming. For me, this was the first time I was attempting something outside of the

On a quiet day in February 2015 in snow packed Boston, I finally landed on “Careers with Paul.” I registered the domain name and put up a quick website. It felt great to take action. It felt like I was moving forward on something that I was excited about.

Within a couple months, I had enhanced the website even more and had re-learned HTML, but was not sharing it with the world or actively finding clients.

Lingering doubts still held me back:

What was I doing?

Can I do this?

What if I’m bad at it?

How do I get started?

But the biggest thing: What will people say? But more on that later…

At this point, I saw a mailing from my alma mater about a career coach that was beginning to work with alums and was intrigued. I quickly sent him an email saying I’d love to connect and see how I could help with alums as well.

That conversation turned into a deeper discussion of what I was trying to accomplish. He asked me the same question: Why haven’t you done anything yet?

I didn’t know it yet, but having someone that saw opportunity and not limits was addicting — I decided to hire him on the spot. Plus, how could I coach other people if I hadn’t put myself through the same challenge?

The Experience Impacted me in Three Powerful Ways

1. Ignoring my self-limiting beliefs — Like many people, I have a laundry list of reasons why I can’t do something. Excuses are easy. But a coach looks past these and focuses your dreams and helps you move in the right direction. This was a powerful emotion I felt consistently while working with the coach. I would say something bold — expecting him to poke holes in my idea — but instead, he would say “that sounds great, when will you do it by?”

2. Having a safe space to consistently reflect: Building a nice website was good fun, but I wasn’t actually learning anything more than CSS and HTML. In each of the coaching session, I kept coming back to the fact that I needed to put my coaching into action to see what I was good at, what I enjoyed and even more important, what I didn’t enjoy or wasn’t good at.

3. Picking a small goal to kick-start action: When I thought about being a career coach, it seemed BIG and overwhelming. I was thinking about the end goal before embarking on the journey. I often tell my clients to pick a small goal and go do it — I needed the same advice. On my first call with the career coach, he said to me “You are already qualified to do this, why don’t you just do it?” So we decided that I would write an article explaining what I was doing and launch the site to everyone I knew in 30 days (here is the original e-mail I sent to 100 family & friends). No excuses. Once I committed to this, everything started flowing. That article was a breakthrough — it led to multiple speeches, helping a client land their “dream job” (their words, not mine), developing an e-book and online course and leading my first group coaching workshop — all in only six months.

So back to my question from above— what will people say?

I still think about it. It never goes away. Criticism is painful, but luckily it rarely comes. What has been more surprising is the incredibly positive reception I’ve received. So many people have emailed me and said how much they appreciate my help, insights or style. One friend even mentioned a small thing I did five years ago and how much she appreciated it. I have faced some skeptics, but the excitement and fun I’m having by experimenting with new ideas outweighs all the haters.

I’m excited for what’s to come and I’m here for you. Just like the coach I worked with, I’m probably going to ignore your weaknesses and when you share your dreams with me, expect to hear:

“That sounds amazing — go do it!”

The Coached Has Become the Coach.

About Paul Millerd

Paul is a writer, creator, and curious human that is passionate about how people can reimagine their relationship with work to do things that matter. He published The Pathless Path in 2022.