Guest Post: My First And Only Experience Working With A Business Coach

My First And Only Experience Working With A Business Coach, Bespoke Hogaboom

TL/DR: if you sense red flags, pay attention. If it sounds like bad advice to you, it probably is. If it feels icky in your gut, trust yourself. 

You know that feeling when the hair on the back of your neck stands up?

A visceral sensation of heat swelling up in your cheeks, a fire in your belly?

That’s your gut talking. And my advice is that you LISTEN to it.


I should start by saying that entrepreneurship was never my plan. 

I don’t have an MBA, I didn’t go to school for marketing, and I did not have a clear road map for my career.

When I met a coach in the winter of 2019, the pandemic was an imminent threat, but most of us didn’t know exactly how much of an impact it would have. 

We met at a volunteer event loosely related to personal style. When this person shared what they did for a living, my eyes lit up. 

I thought, This is someone who has what I want.

And over the next couple of months I would think a lot about that. It made me nervous to put myself out there with a total stranger, but eventually I looked them up online and sent an email. Would they be willing to share a bit more about their business, and see if there were any ways we could support each other?


At the time, I was working at a nine-to-five as a marketing manager for an event technology company that served primarily in-person events. 

By February 2020 it was clear the industry would suffer greatly. 

I feared for my job, my security, my future. 

So I dug deeper. I asked myself some hard questions. The question that kept coming up was, If the world is going to end and tomorrow isn’t promised, what do I want to be doing for the rest of my life?

About that time, the company I worked for took a hard right turn. 

They pivoted all our marketing direction and leadership and sales activity toward virtual and hybrid events. Our staff was selling solutions that didn’t exist yet, and the tech team was tearing out their hair.

It felt opportunistic, disingenuous. I worried for our clients, our partners. I worried for the families of the salespeople who could no longer count on predictable income to provide for their families. I worried for customer service, who were on the frontlines navigating contract cancellation after contract cancellation. Millions of dollars were at stake.

My direct supervisor said in one of our morning meetings, “I don’t give a shit about current customers… we need to reach as many new people as possible, strike while the iron is hot.” 

You mean, take advantage of people amid a global health crisis?

My stomach knotted up. I sweat. 

And I voiced my concerns, in my way, to no avail.

That single interaction sealed the deal:

Capitalism doesn’t give a shit about people. 


I wondered if I had the power to do something different, something that felt less like a perpetual ethical dilemma and more like a dream come true, against all odds?

I knew I wanted to work in personal style, but that wasn’t all I wanted. I wanted more. I wanted something different. I wanted to bring to the world what I never had growing up. I wanted to make an impact.

And in that moment, my first and only goal was to help just one woman in a big way.

But I was insecure. After all, I’d never worked in a professional capacity on personal style before. It was a lifelong interest and skill, but I lacked any social proof.

That led to a desperate craving for validation.

I just didn’t know that at the time.


When I reached out to this business coach (the subject of this post), I had a working plan of action.

From our very first email interaction, I could sense their enthusiasm.

They were eager.

Let’s hop on a call, they said. It will be fun, they said. No pressure.

The exchange felt salesy but not sleazy, and again this person appeared to have what I wanted. There was a lot I could learn.

They asked: would I be interested in being a guinea pig for a service they were thinking of trying out? This was a glorified beta test that would be a mix of business consulting and support, wherein they would share all the steps they took to get where they are and serve as a cheerleader while I took the steps I needed to, to launch.

That’s exactly what I was looking for: some accountability, but also access to someone who had made it happen for themselves. A mentor.

I know now what I really needed, was validation.

This person picked up on my vulnerability and desperation. After an initial 30-minute phone call, they sent me an offer for twelve weeks of coaching. There were no description or details beyond that verbiage except a link to sign up for a monthly payment plan.

I told them I needed time to think it over.

Then came the urgency and pressure to commit

“The only time we really have is now,” they said, or something to that effect.

They got me there. I knew without a doubt that, if I wanted to create my dream job, it would take all of me. Not the crispy-fried, wilty ass, lump of leftovers I turned into at the end of every workday. It would take some serious stamina. Emotional, intellectual, and physical bandwidth.

At least with a coach on my side I knew I wouldn’t be alone. 


There were no touch points between sessions.

Outside of that hour together each week, I was on my own. It was up to me to turn the learning into action.

I had already made the financial commitment, so I soldiered on.

There were other red flags. This person told me (not in these exact words, but you get the picture): Okay, you’ve got to have your core offering. Then you’ll want to build some courses around it. Maybe you have a signature keynote talk, and a mastermind group. And of course you’re going to want a high-ticket retreat type of experience. Something to build toward, a final destination for your clients – the premium package. You’ll probably want to release an e-book, or a series of them, and oh did I mention online course

They told me (again, paraphrasing): the goal is to make as much revenue as you can by doing as little actual work as possible.

Isn’t that what we all dream of?


You know what? I did literally ALL THE WORK to bring my idea to life. 

It was me. I did that. I took myself from concept to clients in three months’ time!

Among other things, I:

  • Built a website on an outdated platform, then rebuilt it
  • Designed an entire brand concept, including the logo
  • Developed my “pitch” and shared it with anyone who would listen
  • Established an active and authentic organic social media presence
  • Joined a bunch of networking groups
  • Purchased my first box of business cards as an entrepreneur
  • Tinkered with my business plan (I really need to dust that ol’ thing off and revise it to align with the major shifts in marketing messaging and updated pricing structure).

I did this all myself.


That’s not to say I didn’t learn anything from this person.

But it started to go wrong in that very first session: this person said to me they thought they’d be hiring me in six months.

You can imagine, as a customer, that didn’t give me much confidence in my investment.

I came looking for expertise, encouragement, and direction – not an empty ego stroke.


The final straw, I call it that because it marked a complete dissolution of trust, was from a piece of positive feedback they shared about one of my proposals.

 “Oh my god this is brilliant, I am so stealing that!


(Still paraphrasing here, except for that last part.)

Not “This is amazing, would you mind if I shared it with my prospects and credited you for the idea/language?” or “Damn, I wish I’d thought of that, good for you!” like you might expect from someone in a position of authority, the mentor to their mentee.

They literally said they planned to steal my intellectual property.

And I had no recourse or protection to save me from it.

I gave it away, for free, and paid for it in pain.


So, that was the final straw, but what happened almost a year after we worked together, was the nail in the coffin:

This person asked if I had time for a short call, that they wanted to share some news but wanted to run it by me first. 

 A couple months earlier I had released a new signature program with a very specific and topical name. When we got on the phone (oops, my mistake) they asked how business was going, specifically had I seen any success with my new program?

You see they were planning to release a “similar” offer in the form of a live, online course, and they wanted to check with me to make sure they weren’t stepping on any toes.

Well, I wasn’t interested in online courses so it didn’t matter. I told them I didn’t care.

The next week I start seeing these posts pop up on my feed from this person’s page. They used the EXACT SAME NAME as my program for their online course!

It has taken me over two years to process the learning from this experience – and almost as long to recover from the sting of humiliation and shame I felt for betraying myself.


When I truly needed Kelly’s course, way back in 2019, it didn’t exist yet. Had I known about the WHOLE ENCHILADA things would have been different, I am sure of that. 

I may not have said yes to the wrong people and projects for so long.

I may have built multiple passive income streams into my financial plan.

Shit, I may not have lost so much money or time or momentum figuring it all out first.

But we don’t get do-overs in this life, and I’m still fucking here.


If you are considering taking a business course, or enlisting the support of a business mentor, coach, or advisor – DO IT! 

Save up your money, make the investment, do it.

We can all benefit from a mentor or coach. 

Entrepreneurship gets lonely AF!

Just make sure whatever person you pick to trust is the right fit for you, and don’t compromise your values or ignore red flags when your gut clearly sees them.

Maggie Greene

Chief Everything Officer | @greenstylemags

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If you like what I have to share, and you’re willing to invest time in your dream – I’d love to work with you formally!

You can read more about my course here (or – get my emails).

You can read about, and apply for, mentorship here.