5 Years In Business, Here’s What I’ve Learned!

5 years in the coaching business, here's the good, bad, and hilarious lessons I've learned!

Hey Coach Ponyling –

I’m back from vacation and *sort of* raring to go.


This year has been so busy, that I actually missed my real 5 year anniversary in business.

The truth is that I have a couple of anniversaries that I think about. The day I quit my job and went full time (My first full day as a coach was March 31, 2012).

The day I finally arrived in San Francisco and stopped faffing about in my business and got focused (early October, 2012).

The day that I realized I could never go back to consulting even if I wanted to, because I had published too many posts on how I hated that kind of work (January 2013).

Note: It took me waaay too long to realize it! But it was a good “wow, the boats are burned so onward!” moment :).

Anyway, those are all milestones for me, and since I’ve now been in business for awhile, I wanted to pause for a moment and reflect on what I’ve learned with the hope that this will help you make even faster progress.

Lesson 1: Success doesn’t happen overnight, but if you keep the eye of the tiger, it WILL happen.

I know this is an obvious lesson, but I think it’s important to talk about it in terms of coaching specifically.

For instance: I used to look at other coaches and compare myself with them. Of course I mostly looked at incredibly successful coaches, so my  comparison only made me feel bad.

Because they had group coaching programs, books, online programs, and retreats, I thought I needed to have all of the above.

So I pushed myself in 100 different directions, constantly coming up with new ideas, and failing to follow through effectively on most of them.

What I realized later is that all coaching businesses tend to start out with ONE product or service, and others are added over the course of years.

So you might start out private coaching, and then in the next year add a group coaching program, and then maybe a year later do your first retreat. So when someone meets you in year 3 or 4 of your business, you have a healthy portfolio of services.

But we don’t often talk about the fact that you didn’t start off that way. In networking conversations when someone compliments you on your business you don’t often respond:

“Yes, but it was really slow the first year and I only had one offering.”

No – you say something like: “Thanks!” and move on.

So I want to pull back the curtain and remind everyone: It takes time.

So it’s okay to be where you are at.

Ignore all of the ads and propaganda telling you that you should be somewhere else in your business.

You are you.

You do things at your pace. And learning and doing takes time.

So be kind to yourself.

Lesson 2: Invest in the Fundamentals.

Every single new coach I’ve met wants to have a big online program or book. Which I support – go for it!

But don’t throw yourself into a half-baked attempt at building a program until you understand how to sell coaching, who you are serving (and why), how to take payment, what makes a website (and sales page) effective, what works in your brand of coaching, and all sorts of other awesome and important stuff.

Invest in the fundamentals of your business (and if you need help with that, join the Build a REAL Business program and I will show you how to do all of the above

Take stock of what you need to learn, and then be uber-focused on that.

So, in the beginning you probably need to learn EVERYTHING. That’s why I say invest in the fundamentals of building a coaching business.

Only then, once you’ve done that and applied what you have learned, can you decide what your next step will be. For each of us it is different, but if you don’t have good fundamentals you won’t get anywhere.

For example, if you invest in learning how to host a good webinar, but you don’t know how to sell, who you are selling to, or how to price and take payment then having a good webinar is pointless.

Bottom line: It’s okay to start at the beginning.

I did invest in my business learning before I quit my day job, because I knew I had no idea what I was doing (DC consulting didn’t prepare me for running a global coaching business).

I wish, looking back, I had invested even more up front in those early days, because it would have helped me focus and land clients more quickly – and I was incredibly stressed in the beginning about getting clients. Everyone is.

(Keep reading for more!)

Lesson 3: Be prepared for intense change, all the time.

My business changes every year.

I tell all of my BARB students that many of them will completely change their niche in the first 6 months of business, because it’s true.

Your business and your focus will change over time.

The reason for this is two-fold:

  1. You often haven’t ever had a  business like this before, so you don’t know what you like (and what you don’t) until you actually try stuff. You may love private coaching, or hate it, but you won’t know till you have some real coaching clients. The same is true for speaking, or group coaching , or anything else.
  2. The environment changes, technology changes FAST, and new opportunities will come your way.

So expect to constantly be learning and changing, and that’s okay.

In fact, it’s awesome!

I started my business thinking I was going to do private coaching, group coaching and retreats.

Now my business is primarily online DIY programs and group coaching.

Along the way I had a period where I spent time writing a book, hosting retreats, and speaking (for fees).

Every year is different as new programs and ideas come my way, and I have different interests and focus. For example, at one point I realized I didn’t want to speak publicly anymore, because getting dressed, traveling, and wearing pants seemed exhausting.

Instead, I wanted to stay at home and reach more people, and that’s when I had a big business shift as I adapted my programs and started marketing my time differently.

Lesson 4: Give yourself some structure so you don’t have to constantly plan your days.

I wrote this post on what I do during the week, day-by-day a year ago if you are curious. I know I do better when I’m not building the plan and executing the plan at the same time, which is why I’m a great believer in structure! 🙂

When I started out I didn’t really plan out my time and I spent a lot of time feeling lost, wondering what I should be doing, and not doing enough big picture strategy and thinking.

True story: There was a lot of stress eating nachos on my couch.

Now, I plan in a few different ways:

  1. When I am putting together a big launch, I plan out the whole thing (and put dates on my calendar and tasks in Asana) up front. I do this before I start working on any of the content.
  2. I have regular structure each week, that is recurring on my calendar. Monday I plan out my week more closely and put things on the calendar to complete, and I actually have time first thing Monday morning allotted to “plan for the plan.”
  3. I also have regular partner and team meetings weekly, to keep us all on the same page. These are all recurring, so all I have to do is show up.
  4. And I own when I’m good and when I’m not (I never talk to anyone not on my team on Monday or Friday, because I am not client-friendly or partner-friendly on those days. I’m mostly in my bathrobe trying to get my act together).

I find it so much easier to just open the calendar, see what I’m supposed to be doing, and do it.

Lesson 5: We all fail, no matter how successful we are.

I kept telling myself that if I just got 1,000 people on my list, I’d be successful. End of story.

Then it was 10,000 people.

Now it’s 100,000 😊.

But in the early days, I thought I’d stop failing big after a certain point. I would have a big enough community that I could do anything!

Oh, how wrong I was!

The truth is that we all fail. I have launches that are a total flop. I know of big name coaches who’ve had products totally fail. And you know what, it’s a relief to know that!

I read somewhere that in this business 70% of our ideas won’t really work, but the 30% that do will cover the rest.

It’s hard, when you are starting out and cash-flow is a huge deal, not to constantly be in desperation. I get it, I’ve had to pay rent too.

So, this is easier said than done, but try and do three things:
1) Get really good at one thing and do that while you learn the next thing, so you lessen your  chances of failure. I used to launch one thing, have it go well to mediocre, and then immediately launch something totally different. I remember my husband saying to me “Can’t you just do the same thing twice and get really good at it?”

2) Treat failure like a science project. Immediately think about what you can learn from the experience and incorporate your learning. It’s not a personal failing to have things not work in your business, instead see them as a sign of growth.

3) Get a good community around you for support and information. This is why Build a REAL Business comes with a supportive and awesome community. Having people around to bounce ideas off of, share inspiration and knowledge, or give you a pep talk can be crucial to your success.

6: Look back at what you have learned and done and acknowledge your progress.

I’m terrible at doing this because I’m always focused on the next thing, but once a year in December I do sit down and take a look at all of my numbers and programs and projects and really look at what has changed from a 30,000 foot progress view. Website traffic year over year, happy clients (and testimonials), growth in other areas, blogs I’ve written. Everything.

Sometimes that’s made the difference for me in terms of keeping my perspective and not being a crazy person.

But look back so you don’t lose sight of your progress and your accomplishments. In the beginning you are constantly overwhelmed, but you are also DOING A LOT. Which is amazing!

Remember to celebrate it.

Want more help for your business? Here are two free things to do right now:

First: Starting a coaching business is hard, and there’s plenty of TERRIBLE and expensive advice out there. But here’s some help that is neither terrible or expensive: A free fancy-pants 26 page guide with the concrete information you need to get your coaching business off the ground.

We’ve been told it’s better and more approachable than The Prosperous Coach, so that’s exciting 😊.

And when you sign up, you’ll get enrolled into Couch School, our free weekly training for coaches that you can do from your couch. Yay!

Second: You’ve seen the stats, over 50% of new businesses, including coaching businesses, will fail in the first year. I’ve been doing deep research on why fantastic new life coaches fail (it’s not the reason you think!) and what to do about it. Read the in-depth series right here!

New Segment: What I’ve done this week

I wanted to start a new blog segment about what I’ve been up to each week, because I know I *always* want to know that about other successful coaches :).

So, to pull back the curtain, this week was my first full week back after getting married.

The takeaway: Ugh. I’ve felt totally off my game this week.

I don’t have wedding blues or anything, I’m just tired and out of my normal routine after the break and craziness – and my attempts at working out to keep me energized have been mediocre. I’ve also eaten a lot of cake, but that’s had no impact I’m sure *wink*.

But anyway – this week was a week to get myself organized because there are several awesome things happening in June for this community. Yay!

So, my high-level goal this week was to get ready and pull together detailed final plan for June, and I’ve *mostly* succeeded. I give myself a solid B :).

My other big goal was to get onboarded with my newest team member, who is 100% advertising focused. As my business grows it’s time to switch focus from free content marketing to paid advertising, and June will mark the first month that I go all-in to this new platform. I decided to hire someone to do the work for me, because after spending the past year heavily educating myself and experimenting with paid advertising, I know it’s not something I want to run for my business.

So this week saw me spending full days doing a lot of homework and prep work for that, checking back in with my team after my break, and catching up on a lot of admin (I hate admin).

I also did a lot of 6 hour days (instead of my usual 8 or 9) and watched an embarrassing amount of Parks and Rec.

Smaller tasks fell by the wayside, and next week I need to up my game. I’m playing with some ideas to help me get back to a good routine, and I’ll share if any of them work.  And..that’s my week!