My seven most painful and powerful lessons from being in the coaching business

Photo: Aigerim Ostapenko

When I first started my business journey, I was high on serotonin. Gone are the days when I have to take orders from others. I can plan my day however I want to, and I’m going to feel so empowered. I’m going to work on my passion, and I will no longer have to work a day in my life, just like the beautiful quote says that I’m sure I had hanging as my fridge magnet.

Well, yes, but no.

The blunt truth is, my journey of building a business has been nothing like roses. It’s been challenging, more challenging than I ever thought it would be, and I still would choose this over anything else.

The following piece is not made to discourage you. Vice versa, it’s meant to encourage you to build your dream, especially because it’s hard. Starting my own service-based business has been the best personal development work that I have ever done, and it continues to be my biggest teacher.

Here I have listed my seven most painful and powerful lessons from building my business. Even if you are not in business or interested in building one, I’m sure it will teach you something about life.

1. Having a straight A-student mentality will not get you far

One of the biggest disadvantages that I’ve had in my life was being an overachiever as a child. I was praised for my good grades and questioned over getting 99 points out of 100. My biggest disappointment when I graduated from school was getting 95 out of 100 for my Estonian essay. I cried for days and thought that I’m the dumbest person ever to be born. I changed my attitude towards grades at university, but I always got pretty good results without working too hard. That mentality made me someone who was highly focused on the outcome and super scared of failing.

When you are afraid of failure, you start trying less, and you are scared to look like a fool, limiting your learning capacity. Learning something new means being in a vulnerable place of not knowing, being willing to make mistakes. Being in business meant being open to constant failure and not beating yourself up for it.

I am comfortable saying that I have failed more than I have succeeded in my business, and it’s been the hard lessons that have built my character. When I started, I was so afraid of every rejection, even people unsubscribing my newsletter felt personal. Not taking the failure personally (most of the time) has been the biggest lesson for me in this journey.

2. Bullying doesn’t end in middle school

One of the hardest and most painful moments of my business was when I was publicly bullied in a couple of FB groups by women. Both of them happened because some people took my words out of context and made them live their own life. It was in the early stages of my business, so it hurt, and it felt like people were throwing rocks at me.

All of this brought up a lot of fear around speaking my truth and expressing myself, which was vital for me to heal. The truth is, there will always be people who misunderstand you, laugh at you, criticise you and especially the more you grow, the more it will happen, but it’s essential to stay grounded in yourself.

I don’t think we can prepare ourselves for it; once it happens, it hurts, but then it’s done, and you move on. When it happens, it always feels bigger than it is. Keep in mind that people who are putting themselves out there are hardly the ones to take others down.

3. Not all collaborations will work out

Once I collaborated with someone we had a great connection with, the energy was high, and we seemed to be very much on the same page. We were organising an event together, we had booked the place, and the details were being rolled out. Then, just before we launched it, she pulled out, saying that one of her friends had come to my workshop and didn’t get any value out of it.

It came completely out of the blue, and I felt disappointed at first, but at the end of the day, did I really want to collaborate with someone who didn’t even trust their own intuition. There was no helpful feedback, just plain criticism.

The truth is, I’ve had many collaborations during my business journey, and I’ve made so many friends with other entrepreneurs. Collaborating with others demands a lot of trust, but it’s ok to try it out. Sometimes it works, sometimes it doesn’t, but I’ve never let fear dictate my decisions, especially when there’s no financial risk involved.

4. Be careful with hot water, someone might get burned

This one is a literal lesson. Once I was hosting a women’s circle, and just as I was about to start the event, I walked into the room with a jug of boiling water for the tea. The moment I entered the room, the bottom of the jar fell off, and part of the boiling water fell on one of the women.

It was a freak accident with an ambulance involved, but luckily she was ok. We decided to continue with the event, and once it was over, I could feel the shock of what had happened.

After that night, I told everyone to pour their water and never walked into that room with a jug anymore. Things happen; it’s important to be careful, but mostly, things happen, and it’s part of life. Sometimes you cannot be prepared.

5. Failed launches and webinars with one signup

The biggest fear that new coaches have is, what if nobody signs up for my webinar; what if nobody shows up for my workshop? I hope it will happen as soon as possible because then it’s out of the way. You no longer have to live with the fear of being rejected in this way.

I’ve had many failed launches, programs and workshops with one signup; workshops cancelled because nobody registered. It always feels disappointing, but it teaches valuable lessons about how to improve the offer and also, it builds character. You can take it personally, or you can focus on what to improve.

Once I announced a webinar, and only one person signed up. I thought of cancelling, but then again, it was that one person whose life could be changed. So I ran the webinar without that person showing up and sent her the replay later on. Sometimes it’s worth cancelling, and sometimes it’s worth going through with it even if it’s only for one person.

6. People will copy your work, and you’ll copy theirs

This one is so common; people complain about someone stealing their work all the time. If it’s not being copied word by word, it’s pretty standard, and it can be very frustrating, but then again, we all are copying each other to an extent. People in the personal development space claim that they have invented revolutionary methods while it’s just put together from different tools that have been around for hundreds of years. Nobody owns the patent for truth and wisdom.

In one of my events, I had a participant who went on and created an event that looked pretty much like mine. I was surprised, but then I wished them well in my head. It’s good to remember that we all borrow inspiration from others, and there truly isn’t anything original in this world anymore. Our ideas are an extension of someone else’s ideas.

If you are scared that someone will steal your ideas, you have to make your work so good that your clients would still prefer you even when someone else is offering the copied version of your work.

7. Don’t be scared to get personal

One of the scariest moments of my life was when I had to publicly announce that I’ve lost my hair and I’m bald. It felt like standing completely naked in front of a crowd of people, out there for everyone to stare. It was so deeply personal, but it was also one of those hard things that I had to do. I was running a coaching business that meant that I was doing regular FB lives, events and workshops, and there was no way to hide.

When I posted my photo on social media, I cried for half an hour straight; it was such a huge release. I was scared that someone will say something that will deeply hurt me, but it was a lesson of vulnerability and being so held by others. Sometimes we are afraid of what will happen when we show our authentic selves, even in our business journey, and once you do it, you’ll be pleasantly surprised how supportive people can be.

I have many more lessons, but these were the most memorable and impactful. Which one of them resonated the most with you? Leave me a comment below. I’d love to hear from you!

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