Hiring A Coach Was The Best Investment I’ve Ever Made

How much was your coaching experience worth to you? my friend asked. I scratched my head and thought about it.

I can’t put a number to it, I responded. It was priceless.

He wouldn’t accept that as an answer. Put another way: would you undo the effects of coaching for $5,000?

Definitely not, I responded.

How about 5 million?

Thinking back to where I was before I got my first coaching session and where I was 8 months later, it pained me to think about unwinding it.

Yeah, probably, I said.

50 thousand?

…No, I wouldn’t.

If somebody offered me $50,000 and said I had to wipe my coaching experience and its effects from my life, I wouldn’t take it.

It wasn’t news to me that coaching has had a big impact on my life, but when I put a number on it, it suddenly struck me how immense that value was.

If someone had offered 6 hours of coaching to me a year ago for $50k, I would have scoffed and said, Hell no. Like many people, I hardly knew what coaching even was. I was lucky to have a friend introduce me to the power of coaching.

Now I’m on a mission to help the rest of the world discover the magic of coaching. In this post I’ll share why I decided to try coaching, how it helped me, and why it was the best investment I’ve ever made.

Why did I decide to try coaching?

I was feeling stuck. I’d recently started dating my best friend but still had lingering feelings for my ex-boyfriend. I didn’t know what to do. My mind felt trapped in a tug of war: should I break up with my friend to avoid hurting him, or do everything possible to wipe my ex from memory? It consumed my mental energy day and night. I couldn’t talk to my new partner about it, and I felt like my friends and family would judge me if I consulted them.

Enter therapy. Facebook ads advertised an effortless way to find a therapist. It was enticing. Then I remembered I had a friend who was a coach. What’s the difference? I asked her.

Therapy examines your past and helps you diagnose your problems, she told me. Coaching focuses on the present and future — and helps you get from where you are to where you want to be.

Based on this, coaching resonated with me more. She offered to do a 30-minute session on the spot and I accepted. An hour flew by and she had transformed my whole way of thinking (I’ll get into this more below).

Fast forward a month — my mind was no longer stuck in an infinite loop about what to do with my relationship. Equipped with a new frame of mind, I overcame my fears and executed the action plan I’d developed with my coach. I was surprised by how easy it was and how quickly I saw positive results.

Once I felt a new sense of clarity in my personal life, I was convinced I needed a coach for professional development. My friend referred me to a coach to help me become more effective at work. Not only did she help me become better at my job, but she also helped me get clear on a question I’d been stewing on for a long time: Should I ask for a raise? (Spoiler alert: the answer was Yes.) A month later, I got a raise and a promotion.

How does my coach help me?

When I think about my coach’s role in my personal and professional growth, some phrases that come to mind are: a cheerleader, a kick in the pants, a detective, a mirror, and a partner in crime.

Some ways my coach helps me are simple: she listens without bias and she holds me accountable to an action plan. Other ways are less clear-cut — providing new perspectives, calling me out on my bullshit, illuminating what’s holding me back.

Let’s go into each a bit more:

Friends, family members, partners, and managers can be great for talking through problems with. After all, that’s what many of them are there for, right?

The problem with these people is that they are all biased by our relationship and shared context. They have vested interests in my outcomes. They’ll project their own experiences onto mine, offering advice that won’t fit my particular situation. This is well-intentioned but not always productive.

A coach has vested interests, too, but they are 100% aligned with mine — to help me be the best version of myself. She isn’t trying to keep me in a particular relationship or job. She won’t project her past onto mine. Her job is to help me achieve my goals. So she provides a neutral sounding board.

When I mull over a problem, I get stuck in the same thought patterns. My coach listens, observes, and reframes the situation in a new light.

When I told my coach about my feelings for two different guys, she reframed the problem. Instead of asking, Would you rather date Person 1 or Person 2? — she guided me to abstract the characteristics of my relationships from the people themselves. She prompted me to articulate what my ideal relationship looks like— and then coached me through the steps to make it reality.

When flooded with intense emotions, it‘s hard to approach situations objectively. My coach helps me step out of raw feelings, break free from unproductive thinking, and see the bigger picture.

As an unbiased listener who offers new perspectives, my coach is an excellent detector of bullshit. And because she’s got my back, she’ll call me out on it.

An example of tough love: After several minutes of listening to me rationalize why I hadn’t taken action, my coach turned to me and said, You’re operating out of fear and scarcity. You’re waiting around as if things will magically change on their own, but they won’t. It struck me like lightning. It was painful but true, and I knew I had to do something about it.

My coach challenges me to be the best version of myself. Sometimes this means directly calling me out when I’m not fulfilling my potential, even if it’s uncomfortable.

Having a growth mindset means believing there’s always room to improve. But we all have saboteurs holding us back, and a coach helps identify, raise awareness around, and combat them.

My coach helped me uncover that “Avoider” is one of my biggest saboteurs. Fear was restraining me, especially in the decision of whether to ask for a raise at work. She recommended I do the exercise of “fear-setting”: take the question “What if I ask for a raise?” and first, define the worst-case scenarios. Then, for each scenario, identify how I would prevent it from happening. If it were to happen, would I repair the situation? Finally, what are the possible positive outcomes of asking for a raise? What are the costs of inaction?

By going through the exercise, I realized that (surprise!) asking for a raise wasn’t that scary after all; in fact, I had to do it. Often the thing we’re most scared of doing is the thing we should be doing. Once I asked for a raise and got it, fear-setting been in my toolkit for tough decisions ever since.

Often the thing we’re most scared of doing is the thing we should be doing.

Possibly the simplest, yet the most powerful way my coach provides value: My coach propels me to take action and holds me accountable for it.

Once I’ve achieved clarity around a topic, my coach pushes me to crystallize next steps: What are you going to do and when will you do it by? She helps me break down my bigger goal into actionable tasks with deadlines.

Having actionable tasks makes the bigger goal less daunting. And having an accountability partner makes me more likely to execute them. The American Society of Training and Development did a study and found that people are 65% likely to meet a goal after committing to another person. And if they build in ongoing meetings with that person to check in on progress, their chances of success increase to 95%.

Why coaching was the best investment I’ve ever made

When I felt stuck in my work and love life, coaching helped me see the light. Could I have reached the same outcomes with the help of say, friends or family? My guess is I could have arrived there eventually. But my loved ones have bias, and sometimes that only makes unproductive thought patterns worse. Without a coach, I bet the journey would have taken a lot longer.

Life is short. Why spend it spinning in circles when there is a more direct path out there?

Not only did coaching help me get unstuck from my immediate problems, it also has had a lasting impact: I’ve become more biased toward action. I catch myself in the act of self-sabotaging behavior and thinking, and I apply frameworks like fear-setting to help me overcome them.

All this is to say, if someone offered me $50k to undo all my coaching experiences, I would respond Hell no! [1][2]

This leads me to believe that coaching was the best investment I’ve ever made.

Why isn’t coaching more of a thing?

My experiences with coaching have led me to wonder: why isn’t coaching more of a thing? I was lucky to have a friend introduce it to me, but why hadn’t I discovered it otherwise? Few people I know have tried it, while almost everyone could benefit from it — whether in career, relationships, health, or another area of life.

One major obstacle is that it’s tough to find the right coach. There are so many out there — how do you know which one is best for you? How do you know if a coach is even good? When we need coaching the most, we don’t have the bandwidth to search for and vet each one.

That’s why I’m creating Uplevel: a platform that matches you with the best coach based on your unique needs. I was lucky to stumble upon coaching and now I want to share its power with the rest of the world.

Want to find the right coach for you? Sign up for Uplevel.

Interested in joining me on my mission to spread coaching across the world? I’d love to hear from you: jen@uplevel.coach.

Shoutout to my awesome coaches Natalie and Arjanna for bringing out the best in me and inspiring this journey!

[1] The “friend” who asked me if I would do that is my partner. My coach helped me realize that in an ideal relationship, I want my partner to challenge me — and because I asked him to, now he does that regularly!

[2] I recognize that I’m incredibly privileged to be in a position where I can say this, and not everyone is. Fortunately, my coaching didn’t cost me $50k, but it still wasn’t cheap. Long-term, I hope that in making coaching more widespread and accessible, I can also make it more affordable to all.