5 Things I Wish They Told Me When I Started Life Coaching

April 20, 2016

In 2010 a college student paid me $400 to help him pick up women.

I know, it surprised me too.

I’m the kind of person who enjoys digging into other people’s problems to avoid my own, so the idea of getting paid to do this was really exciting.

It turned out to be the beginning of a wild ride called life coaching, and I made a lot of mistakes. I spent way too much money on training, I basked in illusions of grandeur and I blurred professional and social lines to the determent of both my myself and my clients.

There were also so many benefits. I became a great salesman, I learned to shut up and listen to people when they talked (almost), and I got to meet some incredible people that I’m still good friends with.

After meeting a lot of new life coaches and watching them make the same mistakes I made, I decided to write out a few things I wish I knew, in hopes it helps others avoid the pitfalls I had to climb out of.

Here are a few of the things I wish I knew when I started.

1. Have patience, then double it.

In 2012 I attended a 2-day coaching seminar and ended up having lunch with a coach who had just made 400K the previous year with no website, no marketing and no business card.

I was blown away by what was possible.

He wasn’t much older than me and from what I could tell, there was no good reason I couldn’t be doing the same thing. Thus began my neurotic quest for 6-figures that I thought it would come “any day now”.

I ended up getting burned out after a year because I wanted results but wasn’t really willing to put in the time to get them.

The hard truth about life coaching, or any business for that matter is that for most people, it takes a long time to build a practice that will support a consistent full-time income. How long exactly? It depends, but it’s usually longer than you think.

Even as I say this, I know there are people that won’t listen (I didn’t). We are the same people that constantly convince ourselves that we’re above average, we can find shortcuts to everything, and that despite the numbers, we are special snowflakes.

If I could send a note to myself when I first started coaching I would have written one simple question.

Are you willing to do this for 10 years?

The answer at the time was “no”. I didn’t see coaching as a career, I saw it as something to do to make some money that I also happen to really enjoy.

When I finally realized what it would take for me to be successful, I saw I actually didn’t love life coaching. If I had realistic expectations about how long success would take from the beginning, it would have saved me a lot of time and stress.

2. Make the money, then spend it.

Here’s something else I would tell myself, and I’d have it as a rule.

Only spend money on coaching after you’ve made that money through coaching clients.


After a year of coaching I hired a coach to help me with my coaching business. I signed a check for $13,750. It was a ton of money for me at the time and I didn’t exactly have it sitting around.

Was he worth it? I honestly don’t know. I learned a lot, but I didn’t see a monetary return on my investment. There were other coaches and consultants out there I could have learned from that wouldn’t have cost nearly as much and would have been just as good.

Looking back, I wish I ran my coaching practice more like a business. Money in, money out. No dipping into savings, no banking on a fantasy future, no exceptions.

3. It’s not who you know — but that helps.

Something occurred to me after watching hundreds of coaches strive to enroll high-paying clients. High-paying clients have the money to spend, and to enroll high paying clients, you need to be around wealthy people.

Are there exceptions to this? Yes. There are people who want coaching so bad they are willing to do whatever it takes, and on top of that we never really know someone’s financial situation, even if we think we do.

Even with these exceptions, I found that as a rule coaches who spent time around wealthy people had more high-paying clients. Coaches who didn’t know many wealthy people started at a disadvantage, and while they could overcome it, the advantage that some coaches had starting out was significant enough to not dismiss.

It’s a bit like this brilliant cartoon exposing the unseen side of privilege.

This isn’t to say that we should use our social circle as an excuse, and that we shouldn’t focus on being a great coach. All that is true. But it’s worth considering how the people we associate with determine our ability to meet high-paying clients.

4. Some clients will manipulate you with money.

This is a typical situation I found myself and many other coaches in.

  • A coach has been coaching for a few years and is making a few thousand dollars a month. He wants to be charging more and finally meets a new client who has a great job and can afford a higher fee. The coach makes a proposal for triple what he usually charges and the new client says yes.
  • They begin working together and the coach unconsciously becomes attached to his new client. In fact, after doing some math the coach realizes that half his monthly income is now coming from this one client.
  • The client starts to blur the lines of professionalism. Maybe he doesn’t know any better, maybe he’s testing the coach, or maybe he’s just lonely and wants a buddy. Instead of maintaining his professional relationship the coach lets things slide and aims to please the client by making exceptions for him. He doesn’t want to have the hard conversations and tell his client the hard truths because he doesn’t want to lose him.
  • The client begins to lose value in the coaching relationship that once served him and the coach, sensing this, pleases him even more until finally they stop working together.

I went through this, and I saw many other coaches do this as well. Learning to not act from a place of need is a lesson every coach needs to learn, as well as learning when to say no to clients, even if it risks ending the relationship.

5. Don’t sell coaching to your friends.

When I stopped (officially) coaching in 2014 I felt a huge sense of relief and it was for the simple fact that I no longer had to enroll everyone I met, especially my friends.

Before I get into this I want to say that I’m sure a lot of coaches have found a balance with this, but I was terrible at it. I made so little distinction between my social life and professional life that I was constantly turning conversations into “deep coaching conversations” and looking for how I could be of service, even in the check out line at the grocery store.

It practically drove me insane, but it didn’t even occur to me until I stopped. It was then I understood how draining it was to see all my friends as potential clients.

Are there exceptions to this rule as well? Yes. For some coaches, simply telling people that you’re a life coach is a big breakthrough, so for some people actually putting yourself out into the world is a great practice.

I tend to overshare, meaning I don’t have a problem not telling people what I do, so for me having a clear line between my professional and social life would have really improved my mental health.

In Conclusion

I love life coaching, but right now it’s in an awkward phase where everyone and their mother is becoming a life coach, and there’s no standard for how to do it.

There are organizations that sell you permission in the form of an expensive training program, there are people out there making millions, while other struggle to get someone to say yes to $100, and there’s everything in between.

Ultimately as a life coach, you get to make your own rules, which is both good and bad news. The good news is there’s freedom in deciding for yourself how your career should look. The bad news is you may have to learn everything the hard way, but hopefully in learning from the mistakes of others, it doesn’t have to be as hard.


Michael McDonald, my philosophical sparring buddy and wonderful life coach hoped on skype with me and we had a conversation about this. It’s long and my hair looks ridiculous but you can watch the entire conversation on YouTube.

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