The Best and Worst Coaches I’ve Ever Had (Detailed Description)

A coach is someone who tells you what you don't want to hear and who has you see what you don't want to see so you can be who you have always known you could be.

Coaches: they make us believe that anything is possible for us.

They inspire us to want more.

Is this healthy? Are we all being fooled? Is everything, in fact, a pyramid scheme?

I’ve had -- and paid a lot of money to -- a few coaches in my life. I’ve also been a coach, receiving money for my time.

In a moment, I’m going to share a story about my worst and best experiences when paying a coach to help me.

But first, let’s look at why people seek change through coaching in the first place.

99% of the modern population craves:

1. Respect

2. Approval

3. Validation

An appetite that continues to renew itself but is never fully satisfied.

The tricky thing about appetite is that if you don’t manage your appetites, they will run your life.

To experience the best that the world has to offer, you must overcome these cravings.

We’ve been warned time and time again by celebrities and athletes: when you make it to the top of the mountain (win the Grammy, score the date, earn the pride of your parents), you’ll be presented with the ultimate lesson: those things still do not satisfy your craving to solve the ultimate question.

At some point in each of our lives, we face this question: am I valuable and important?

If we believe we’re not, we will operate and act from these places:

1. Emptiness: I am not full so I need to eat/drink/shop/work to fill the void that I am feeling

2. Victimhood: I am not worthy so I need to do and achieve in order to earn my value

3. Pride: I am not respected so I show people I am something worthy of admiration

This is how you feel after a good scroll on social media. Your insecurities are tempted by others showing you, with confidence, the best that the world has to offer.

You start to believe, “I want to go there and I want to do that.”

You believe that, if you act like them, you get to feel the way that you perceive they feel based on what they show you: confident, secure, mature, and put together.

So you buy into their sales pitch and start to believe that there is something you need in order to fill your void, prove your value, or be respected.

99% of the time you think it’s about them – they are influencing you to improve your life.

Reality check: 100% of the time, it’s about you.

Let’s go deeper.

Would You Rather Be Respected or Worshipped?

It’s not only that your insecurities are awakened -- so is your appetite for people to look at you the way that you look at the influencer. For people to see you and feel about you the way that you have looked and thought about them – valuable, influential, important: worshiped.

There is a long, long distance between being worshiped and being respected.

One is an image of perfection. One is the reality of humility.

One asks people to look up at you on a pedestal. The other is having them look to you as an example.

Respect is an inside job.

It is not earned, or bought -- it is taught. And it can only teach others how to treat you when you have done the work to treat yourself with respect first – when you know what it looks like, and are an expert in respecting yourself.

Stop operating to fill a void or prove a point.

Where you want to operate from is:

1. Fullness: You’re already full and nourished with the love and approval of yourself

2. Purpose: There is a problem you’re uniquely designed or learned to help with

3. Humility: You operate from a place of humility, teaching others to respect you

This is your rock-solid foundation of identity.

Knowing you are human is a superpower.

It’s ok to have a mentor or coach.

Standards are good to have.

Having healthy examples of what a good friend, partner, or employee looks like is really helpful.

Just pay attention – who or what is the person you’re learning from?

Is the person you’re following on Instagram pridefully following their ego, hungry to be worshiped with likes? Or are they humbling following a purpose that is greater than themselves because they’re already so full that they have enough to pour out onto others?

The Best and Worst Coaches I’ve Ever Had

I’ve had, and paid a lot of money, to a few coaches in my life. I’ve also been a coach, receiving money to do so.

I share these experiences having been on both sides:

The Worst Coach I Ever Had

One coach cost $8,000 for three months. They didn’t have a contract to sign, but sent me an email about what I could expect. I wasn’t allowed to speak with them before signing up for 1:1 mentorship. They had over one million followers on Instagram.

My experience under their mentorship:

• They delivered less than 25% of what they offered me in their email.

• They had no roadmap for me and were not able to show me where we were going.

• They asked me my goals on day one and not once ever mentioned them or referenced them again.

• They lacked integrity and accountability. I had to hold them accountable to holding me accountable.

• They pointed me to additional resources (that cost more money) as a quick fix to the problems I was facing.

• They handed me the equivalent of a 200 page textbook and said, “Good luck, let me know if you have any questions.”

• When I respectfully communicated that the service was underdelivering, they offered me 6 more months of additional shitty mentorship for “free.”

This person has no self-respect and no respect for me. They cared about reputation (ie. people worship them) more than respect.

I digress.

The Best Coach I Ever Had 

The other coach cost $10,000 for six months. They had an extensive contract. I was able to speak with my coach and with several references before committing to mentorship. They had less than 10,000 followers on instagram.

My experience under their mentorship:

• The first thing we did was create a 6-month plan.

• I was placed into a small community for weekly group coaching and received 2 private coaching calls a week.

• Each week they helped me clarify required actions for progress and held me accountable to that progress.

• They employed (and paid) me to be of service to others in a way that developed the skills I required for my own success.

• If I lacked follow-through, we dove deep into the psychology of what was holding me back -- mentally, emotionally, and spiritually.

• Plus 10+ other amazing offerings and experiences.

I was taught how to show up and how to respect them. They respected me every step of the way.

I transformed.

The difference between those two experiences was this:

1. The first had successfully convinced me that I was missing something that they could help me get (i.e. the worship of other people and their money to prove it!)

2. The second humbly believed that I already had everything I needed to be full and abundant (teaching me how to be my own coach and overcome any obstacle)

Be it someone you follow on instagram or your current significant other: don’t fall in love with people who make you feel like you’re missing something.

Fall in love with people who make you ever-more certain of what you already know to be true.

Be willing to face the rejection of those who make you feel that you need to fill yourself with something (food, drink, fashion, money, followers) in order to approve of yourself.

What Do You Need?

Have you ever had a coach?

I’m a high-maintenance woman and I relish having support in a lot of different areas of my life.

I’m currently being coached in or belong to a community empowering:

1. Sobriety

2. Spirituality/faith

3. Building long-lasting, meaningful relationships

In the next 3 months I’d like to add “learning piano” to that list.

I don’t mind being high-maintenance -- after all, I’m the one maintaining it.

I’m curious… if you could have a coach now -- for anything -- what would it be for?

I hope you found value in this letter.

Thanks for reading.

Jenna Lou