My Entrepreneurial Journey


What Drew Me To Become An Entrepreneur?

I had been waitressing for a million years, ok actual time 15 years. If you have ever served before, you understand it’s essentially the opposite of working for yourself. You take orders from managers, bartenders, supervisors, the kitchen, and or course guests. You are extremely replaceable, and the money you make depends directly on your shifts and sections, which often depends on how much your supervisors like you. You usually have pretty much no say as to how your shift is going to turn out, and your recommendations usually fall on deaf ears.

After years of this, I really hated serving. Working for myself sounded like a magical dream, unicorns, rainbows, and cash money! I could pick my own hours, I made the rules, ultimately I was in control.

If you know me, you know I am super organized, and love being in control. After I became certified as a Health Coach, I knew instantly I wanted to start my own practice, be my own boss, and be in control

Woah, Not As Easy As I Thought

And then my magical dream turned out not exactly as I had planned.

I didn’t fully grasp how much work it was going to be. Of course you can hire a team of people to get your business off the ground, but this takes money I just didn’t have. I was a one man show, and it was so much work.

I went into it thinking I was a Health Coach. I had no training in business, marketing, website design, SEO, and the list goes on…forever.

I quickly realized that if something needed to get done, I was the only person that could do it. I had to learn skills on the fly and to be honest…

i had to fail, and then fail again, and again, and maybe one more time


I had to try out everything that didn’t work first.

I’ll give you some examples:

  • I held a cooking class, and put flyers up everywhere, told everyone I knew, posted it on social media…and then no one showed up (but I did video tape me doing the cooking class anyway, which I used for future clients)
  • I spent a lot of money on flyers for my services and posted them everywhere…no one called
  • I started blogging and growing my traffic, but wasn’t collecting email addresses to contact anyone further
  • My first website in general was pretty inefficient , who am I kidding, it was terrible
  • When I finally got business cards, I didn’t carry them with me, they just lived at home (serious!)
  • tried to hold a teleclass without testing the technology first…mhmmm
  • I’ve held workshops where no one has shown up because I left all the marketing up to the centre I was holding the workshops
  • I’ve paid to be in trade shows where I didn’t try to collect any information, I just gave away so much marketing material, and no one called me

Yup, I fucked up. I failed, and then I failed some more. I wasted time, money, effort, and tears. I felt embarassed, ashamed, lost, stuck, and super stressed about money.

But, I did make it through.

How To Make It Through

So yes, I made every rookie mistake you can think of, I overworked myself, I took time away from my business, and I cried more than once.

But I did make it through.

The best thing I did, was not repeat my mistakes. If I did something that went horrible, I always reflected on what happened in a journal, or talking with a friend. I would go over what happened, and why it happened. Without judgement. I would try to figure out what the hell went wrong, and then never do that again.

For example, I put on a cooking class, in a new town, slapped up some posters, marketed on social media to no one that lived there, and then shocker, no one showed up. I know it seems super obvious now, but at the time, it was sad. I talked it over with a good friend, just by hearing myself, I knew where I had went wrong.

Now when I put on workshops, cooking classes, etc I approach places that already have a group of people I can market to, like a gym for example. I look for somewhere that is already hosting cooking classes, and approach them to host one for me. This puts me in front of their audience, and ensures I have an audience at all.

I always think of a scene in Elizabethtown:


How I Got My First Clients?

Ok so I shit the bed, a lot, we got that, I learned from my mistakes, and starting doing things that actually were working and I started getting clients! Woot Woot!

But what exactly was working?

Firstly, I walked my talk. I posted pictures of green juices, I posted healthy recipes, I brought super healthy food to work, and to parties, I followed all my own recommendations. I felt amazing, and it showed.

Then I approached people that were closest to me, I told them what I was up to and offered a free coaching session to everyone to try it out no strings attached. I got a few clients.

I made a plan. I wrote a list of things I wanted to do, workshops, referral partners, and get published. I thought that these would be the best ways to get clients. Then I would start with one thing, for me I got published first.

I contacted the local paper, put together a few of my articles from my blog, a bio, a cover letter, basically a little press kit. I googled who the editor was and got his contact info. I went in and dropped it off. And then I stalked him. Just kidding… I legit called him back and left messages, emailed him, and went in 3 times looking for him. He was on vacation for a week, but it did take me 3 weeks to actually get a hold of him.

I had a meeting, where he said he couldn’t pay me, but if I was willing to submit my articles for free, he would publish 12 articles once a week for 3 months. I said I would only go without pay as long as I could have a pitch and my number and website at the end of each article, and he said yes. And I almost hugged him.

I started getting clients from this.

Now that my articles were set in motion, I moved on to referral partners. I researched other wellness practitioners and reached out to them to set up meetings where I could find out about their business, and talk about what I do, how our business could compliment each other, and give them brochures and business cards they could hand out to their clients. I also used this time to book workshops.

One thing that I found super helpful during my cold calls, was to focus on wanting more information about their practice so I could refer my clients to them. I absolutely have clients that have problems outside of the scope of my practice and I recommend they see acupuncturists, massage therapists, chiropractors, naturopathic doctors, and so on all the time. I feel much more comfortable knowing who I am sending them to once I have a meeting and try their services.

Once I had brochures all over town, my articles were coming out once a week with my picture and contact information, and I had monthly workshops scheduled, doors started opening and clients started calling.

My Biggest Lesson I Learned (The Hard Way)

Don’t wait til you have it perfect. As Marie Forleo says: Progress Not Perfection

This is the biggest game changer for me. Once I let go of being perfect, of feeling ready, I embraced feeling the fear and doing it anyway.

I was never going to feel ready to do something I had never done before. I think about it like cliff jumping into the lake. If you just run and jump off, you’re committed and the fear ends when you hit the water. If you look over the edge and think about how far it is, and stand there for a few minutes, you’re going to start playing the what if game and your fear is going to multiple by the millisecond. I can hear your friends making fun of you until you just run and jump AND your fear won’t end til you hit the water anyway. Don’t prolong the agony, just start making choices, getting out there and listening to your gut.

What’s the worst that is going to happen? You might fail? So what!!

If it doesn’t work, go back to the drawing board, figure out what happened and come up with a new plan. Even when you fail you are making progress, moving forward, by learning what doesn’t work.


Feel the fear and do it anyway, just fucking jump!

What is your story? What is your best advice for entrepreneurs? Help us out in the comments below!

About Amanda Greenthumb

Hey, I’m Amanda! I help busy, successful women feel FEARLESS, SEXY AND HEALTHY by teaching them everything they need to know about food, how to have more energy and boost self-confidence to fall in love with their life. I have two coaching programs The Fearless, Sexy and Healthy Group Coaching, and The Elite Private Coaching Program. I am also the creator of Naturally Conquer Your Cravings the free 7 day E-Course, and a blogger at

6 comments on “My Entrepreneurial Journey

  1. This is a really inspiring post! I read so many posts where people’s don’t know how to connect their stories to my experience. This manages to be both your story, and also many of our stories, even when it’s specific. I really like the way you didn’t start spinning fables in your mind about why certain things didn’t work immediately, but rather made a strategy, from the inside-out. You have inspired me today!

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