The Unedited Truth About What You Really Sign Up For When Hiring A Life Coach

“Can we work by candlelight?”

I tried to lighten the mood, as fear and uncertainty gripped my management team. We had just learned that a lead investor pulled out of our latest round of funding. Without the capital, we were at an uncertain and frightening crossroads. How would we keep the lights on? And what about payroll? To make matters worse, a shakedown artist who apparently misjudged our resources was threatening a lawsuit. Joke’s on them though—suing a start-up is like complaining to Denny’s that your lobster isn’t fresh.

But it wasn’t only my business that was stressing me out. My personal life had taken a nosedive. For the past four years, I had sacrificed dating, sleeping, and healthy habits for a “minimum viable lifestyle” that gave me more time and money to reinvest into the company. One evening, as I stared into a microwave meal from Walgreens that resembled a high school science project, it hit me:

I needed a life coach.

I wanted to find my own sensei to lead the way—someone like Wendy Rhoades from Showtime’s Billions. So, my search began. I googled, dug through, and even ventured onto Yelp. I was hopeful, but things took a weird turn.

I scheduled a “get to know you call” with 13 coaches. I wanted to paint a picture for them and see how they responded. So I would summarize my business challenges, explain that I was eating lab-made tuna salad from a pharmacy, and cop to the car accident I caused where the guy was so freaked out by my vibe he actually left the scene without getting my info. Hopefully one of these coaches would understand how to clear out mental clutter and help me reconnect with my gut. So the vetting calls commenced.

During these conversations, I noticed some trends. Several wanted to be supportive and listen; others wanted to change my habits; a few wanted to quantify my problems and plug them into a formula for analysis. Others wanted to figure out what I could do for them. One thing they all shared, though, was an expensive price tag.

Here are five styles that will forever define my understanding of “life coach:”

The Overconfident Imposter

“G” told me he only had 15 minutes for our call, so I had to be quick. Yes, his first name was a single letter of the alphabet. He was younger than the other coaches, late 20s or early 30s. His experience included travel, spiritual exploration, and a prestigious education, followed by entry into life-coaching (the wunderkind skipped work experience and went straight to coaching others).

During our call, which lasted exactly 11 minutes, G didn’t ask me a single question about myself. I summarized my struggles, and he said he understood and asked me what questions I had for him. Well, if he was going to be coaching me, then I had to know. “Why is your name a single letter?” I asked. After college, G explained, he left behind a life of a Gary or a Gregory because he had an itch. That’s it? Well, I can’t blame the guy for trying to be interesting.

I also asked him why he felt he was uniquely qualified to be a life coach. “I have a great bullshit detector. I just know when people are lying to themselves,” he replied. (Me too, G. Me too.)

My takeaway: If something feels like it’s missing, don’t wait for the reveal. A red flag is often the precursor of more red flags.

The Validator

Fawn was empathetic. She told me I am a whole person, and that there’s no such thing as a mistake. Everything we do, she explained, is part of our journey and makes us who we are. We only briefly covered my business issues. She wanted me not to be so hard on myself. Her approach left me confused. How can I break the cycle of making mistakes if I don’t acknowledge that mistakes are a thing? If I’m already fixed and whole, what’s left for her to help me with?

My takeaway: Validation is great if you have low self-esteem. But if you have a business to save and shit’s getting real, find someone who won’t back down from telling you that you’re screwing up.

The Homogenizer

Melinda had a more corporate approach. She ran a framework-driven operation and had developed a set of templates and exercises that she swore worked for everyone, no matter their situation. For her to become my coach, I would have to complete a discovery package asking about my strengths, weaknesses, fears, and so on. It would take a few hours to complete. The discovery package would theoretically reveal my values, dreams, fears, goals, insecurities, limiting beliefs, true motivations, and everything else. This first phase of coaching—the assessment—would cost $7,000. I was confused. If I have enough insight to complete an assignment like this before even starting, why do I need a coach?

My takeaway: Perhaps I don’t value myself enough to spend $7,000 to fill out a 50-page template that will turn my life story into a series of data points for analysis. Or, if people really do spend this kind of money to do homework assignments as adults, maybe I should switch fields and become a life coach myself!

The Covert Hustler

Hope was the most spiritual of all the coaches. She ran meditation retreats, focused on supporting women through life changes, and generally emitted more empathy than the others. Yet she remained grounded in reality and was not too far gone down the path of reiki and crystal healing. During our call, she asked about my values in life and business. We talked about leadership and navigating through murky times. We also talked about life goals, and she led me on a meditative visualization. It’s not the kind of thing I’m usually game for, but she made me very comfortable. Hope skillfully toggled between spiritual connectivity with a greater purpose and real-world savvy. She understood both my feelings and plans. I felt vulnerable and empowered. Maybe she was the one. At the end of our initial call, I thanked her and said I would think it over for a day or two, and let her know.

Her response took me by surprise. She offered, “Of course. I just want you to keep in mind that it sounds like solid leadership is very important to you and your business right now. Do you know what studies have shown to be the most important characteristic of a good leader? It’s quick decision-making. You should quickly make gut-driven decisions as soon as you know something is right.”

Whoa, full stop.

My takeaway: This final moment of harmless manipulation closed the door on the most promising relationship in my coaching lineup. We entrepreneurs know how to spot a hustle, and don’t enjoy being on the wrong end of one.

The Horse Trader

Finally, Larissa—the “celebrity coach.” Larissa had the most impressive website, shout-outs from well-known personalities, a few books, and a Twitter account seemingly brimming with followers. It was worth a call, even if I wouldn’t be able to afford her time.

During our initial call, I shared some background about my challenges and why I was seeking coaching. In response, as if to also share, she told me about her life. I learned that she had been married three times and was abused as a child. And she boasted about success with a previous coaching client whom she had empowered to finally achieve their dream of speaking on stage. I racked my brain. What did all this have to do with me? But I hung in there.

Larissa also made an interesting offer. She usually charged corporate clients $25,000 and up (allegedly). But she offered not to charge me at all. Instead, she suggested a quid-pro-quo. She would provide coaching, and I would offer business and strategy consulting on a new venture she was working on. It seemed a little off-beat, but I was willing to listen.

Under this proposed arrangement, she would also be my client. I didn’t know if I wanted to muddy up the sanctity of a coaching relationship by also making myself professionally accountable to her. Still, I decided to give it a shot.

As it turns out, “free” coaching didn’t mean free at all. Even quid-pro-quo looked like it might turn into quo-pro-quo. Not only did our coaching sessions amount to a churn at the rumor mill, but I now owed her my time as a business consultant in return for this gossip session about her life.

My takeaway: There’s no such thing as a good deal. You will always get a maximum of what you pay for.

And so, my search for a life coach hit some snags. I still haven’t found my Wendy Rhoades. But I did gain something valuable in choosing not to hire any of them—a reminder of some basic human truths, and a journey back to what I had been looking for all along: my gut.

(Note: Names have been changed for privacy)

Entrepreneur, 2x founder, analyzer of people, teams, & culture

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