The 3 Biggest Mistakes I've Made in My Online Coaching Business (and How You Can Avoid Them) -

The 3 Biggest Mistakes I’ve Made in My Online Coaching Business (and How You Can Avoid Them)

In this post, I want to share with you the 3 biggest mistakes I’ve made since I started earning a living online about 3 years ago.

It’s been said that: “Only a fool learns from his own mistakes. The wise man learns from the mistakes of others.”

My hope is that you’ll be wise and learn from my mistakes so you can avoid the many time-sucking traps and money draining potholes and instead make progress faster and avoid frustrations that can leave your head pounding like a drum.

…by the way, I suggest you stick around until the end…there’s a really powerful tip down there…

Mistake #1 Not Getting Started Sooner

This is probably my top mistake online so far.

I heard about selling my expertise online in 2005 back when people were calling courses “information products”.

The idea of creating passive income pulling digital products captured my attention back then, but, like so many people, I did NOTHING about it.

I invested my time and money in books and programs to “learn” about it…but I took no action.

Now, I feel like the person who regrets not investing in Google in the early days.

It wasn’t until 2015 that I made my first attempt selling something online.  Oh, how I wish I would have gotten started sooner…

There is a real advantage to getting into opportunities early.  But, the not so obvious advantage is all the learning that could have taken place over the course of a decade.

You see, success in online business (and business in general for that matter) is usually not about hitting a home run on your first at-bat.

It’s about stepping up to the plate, striking out, then stepping up again, getting walked or hit with a pitch…trying again and maybe getting a single or double…but constantly learning, adapting and growing along the way.

…but enough with the baseball metaphors (I don’t even like baseball).

The fact is I’d be so much further along now if I’d gotten started when I first felt inspired to do it 10 years ago.

Don’t get me wrong, I’m glad I got started when I did because even though the best time to get started was in the beginning, the second best time is NOW.

Mistake #2 Being Too Conservative

This is a big one…it was basically being too risk-averse.  The most obvious example of this was I tried to learn everything myself instead of investing in private coaching.


Simply because I had it stuck in my mind that 1) coaching was too expensive and 2) That somehow I couldn’t afford it…even though I really didn’t know how much it actually cost.

No, I was going to be “smart” and learn what I needed to by investing in courses and books…I was going to get that information for less or better year for free online. (forehead slap)

…little did I know I was stepping over a dollar to save a dime.

In reality, the money and opportunity it cost me by not having a competent coach was far more than the money I thought I was saving.

Just like the first mistake, I would be further along had I taken the risk earlier.

To be clear, I’ve invested in coaches that haven’t panned out or resulted in a positive ROI.

…but people underestimate the ROI that comes from having a good business coach in your corner.

Beyond the mental hurdles and unconscious blocks, they can help you overcome…

Beyond the time they can save you by helping you stop procrastinating…

In concrete, real-world terms, a solid business coach can pay for themselves before the coaching program is over and more importantly teach you how to implement something that can earn you money for years into the future.

2 out of 3 of the business coaches I’ve hired have resulted in an immediate positive ROI.

The ROI from the most successful coaching relationship I’ve had would have paid the fees for all 3, plus 3 failures in the future and still be producing an ROI long into the future.

..wish I would have pulled that trigger on that earlier.

But, hey, I thought I was being smart by being conservative….oh the time I wasted.

The other area of being too conservative was not being willing to pay for ads….and while I built my business up to 6 figures without spending a nickel on advertising, I wish I would have gotten started with that sooner too.

I still don’t recommend beginners start with paid ads because there are other things that need to happen first and it’s easy to lose money if you don’t know what you’re doing.

–>To learn some of the first steps I think beginning coaches should take, check out the Free 7-Min Cheat Sheet for Beginner Coaches.

Mistake #3 Not Valuing My Expertise Enough

This is a particularly damaging mistake that I’ve made and that I see a lot of coaches and subject matter experts making…especially when getting started.

…but some never really stop making it.

It’s one you have to constantly work to avoid, at every stage of your professional development.

It’s insidious and will eat away at the foundation of your business and undermine ALL of your efforts.

Let’s take a look at how this hinders us:

As a beginner, not valuing your expertise will stop you from ever getting started in the first place.

When I was first starting out, I constantly had self-doubt and would think things like “who am I to teach a course?”, “nobody is going to like my programs” and “nobody is going to buy what I’m offering”.

This lack of belief in the value of what you do will cause you to accept terms and “opportunities” that really don’t serve you and will cause you to waste your precious time.

It will cause you to charge too little for what you do or worse to give away free consulting and expertise that you spent a lifetime and probably a small fortune acquiring, as was the case for me.

This is a mistake that you need not make.

Look, if what you do solves a major problem for someone in their business or personal lives, then you deserve to be paid well for your expertise and guidance.

So, the first tip I can give you to help you avoid this mistake is:

Don’t charge for your time, charge for the results and transformation that you provide.

If you can help someone save their marriage, how much is that worth to them?  Might save them a ton of money in attorney and therapy fees.  (Just saying.)

If you can help someone double their business and you’re scared to ask for $5 or $10k then you must not believe you can help them.

The next tip is to consider the wider implications of the problems you solve for your clients.

An easy way to do that is to look at the primary problem you solve and ask: what are the consequences of them solving this problem?

If you’re a weight loss coach and can help someone lose 20 lbs and get that sexy body they’ve always wanted, write down all the consequences of that:

  • Lose 20 lbs
    • Feel better about themselves (how valuable is that?)
    • Fit into that dress they love
    • Positive comments from their friends and family
    • Increased belief in their ability to change their life
    • Feeling stronger
    • Feel sexy
    • Feeling more energetic
    • Fewer fears about their health because now they are living a healthier lifestyle
    • Having their spouse or significant other attracted to them again

…and you could keep adding to that list.

Now, look at that list and what I want you to realize is that:

You’re not just helping someone lose 20 lbs.

It’s the consequences of that result that are of most value.

Look at all those things….how much would that be worth to your client?

…some may be priceless. (reminds me of those old commercials…here’s something to make you smile)

Make your own list and review it before you do your discovery calls so you feel completely confident asking for your coaching fee as you realize the REAL value you’re providing.

So those are the 3 biggest mistakes I’ve made since earning a living online full-time.

It’s highly likely that if you’re reading this, you’re still making one or more of these mistakes.

You now have a choice, you can continue to waste your time, money and miss opportunities by ignoring these warnings…

…or you can get further faster, avoid many avoidable frustrations and get the results in your business and life that you would have missed out on.

So, look at your own life: 

Where are you not starting something that you know you should and really want to?  

Where are you being too conservative and afraid to invest in yourself?

Where are you not valuing your expertise enough and how is it affecting every aspect of your business?

If you found this helpful and would like to learn how I help coaches generate full-time passive income streams + highly targeted, high ticket coaching clients without blogging, social media, sales funnels or paid ads….even if you’re an absolute beginner, then click here to book a brief, no-pressure call with me.



  • Ken
  • April 25, 2018