5 Surprising Lessons From My First 6 Months Of Online Coaching

On October 29, 2014, at 3:58 PM my first client signed up for coaching.

Online coaching, that is.

If you have no idea what online coaching is, you are where I was just 7 months ago, right before an important email hit my inbox.

Note: Pressed for time? Check out the 5-step-recap and bonus download at the end of this post.

Tony Stubblebine, CEO of coach.me, reached out to people who were doing well in the NOBNOM challenge, as proposed by Tim Ferriss.

NOBNOM is an acronym for no booze, no masturbation. Tim decided to abstain from both of these for 30 days, beginning August 1st, and run his experiment publicly through the startup, to which he is both investor and advisor.

Trying to kick both of these habits for quite some time, I decided to join on August 21st, and though I was late to the party, I did well.

The app helps you stick to habits and thus achieve your goals. You can check in daily to create streaks – a powerful visual encouragement. You can also follow others, give them props, as well as ask and answer questions.

I had been using the app since the beginning of 2014 and the NOBNOM challenge was a great way to put my knowledge to good use. I had a lot of fun upgrading myself, answering questions, encouraging others and seeing them succeed.

If you’ve read the section about the purpose of this blog, you know I’m striving to help as many people as possible (if you haven’t, do so here).

So when Tony asked me whether I wanted to use my NOBNOM experience to help others and get paid for it, all I could say was: “Where do I sign up?” (there was a link in his email, so I’m glad I didn’t actually respond to him with this, which was my initial reaction).

Note: Never mind that my initial 3 week streak in NOBNOM ended exactly the day Tony emailed me. Due to which of the two, I’ll leave to your imagination. Keep reading to find out how long my current streak is.

A few seminars, many emails and hundreds of adjustments to my coaching profile later, I received said first client. Since, I have been lucky enough to be part of the small team exploring online coaching territory for the first time in history.

The premise of online coaching is this (quoted from the official coaching training):

Coaches communicate with clients through a chat feature inside the app. A client signs up for a single goal with a coach. An automated welcome message is sent by the coach.

Coaches are required to reach out to a new client within 24 hours to help make sure the client is ready to start making progress on that goal.

Then coaches and clients check in with each other nearly every day. The main purpose is to hold a client accountable to a goal and help them build momentum. The coaches secondary purpose is to answer any questions a client may have.

Think of it as a very focused and useful facebook chat with a friend who’s done what you are trying to do. Your coach tries to help you achieve one specific goal by motivating you, giving advice, pointing you in the right direction and holding you accountable.

I was among the first 200 coaches to sign up (if I deciphered the links correctly my number is 122) – by now this number has more than quadrupled.

Now, 1 free video course, 3 features, 6 months, 10 testimonials, 58 clients, 100s of hours of coaching and about 1,300 coaching chat messages later, I’d like to share what I learned.

1. Anyone can be an online coach

Before, when I heard the word coach my mind would jump to this image of an old man in a sweat suit. I think it might actually have been John Wooden (possibly the greatest basketball coach of all time). I connected the word coach with someone who has decades of experience, is unrivaled in his or her wisdom, and has the answers to all my questions.

Being an online coach has changed my perspective. Coach.me tears down the image of a coach as the final destination and instead makes him or her a mere stop along the way – which relieves a lot of the pressure to perform.

You don’t have to be Tony Robbins to cure someone’s stutter.

You only have to cure your own stutter. Then you can help someone else lose theirs.

According to Wikipedia “coaching differs from mentoring in focusing on competence specifics, as opposed to general overall development.”

What Wikipedia says in complex words is that in order to coach someone, all you need is to be better than them at the skill you are coaching.

Online coaching makes the most of this by breaking coaches down by goals. I get to decide which goals I want to coach and I only pick the ones in which I feel comfortable enough to teach them (for me those are cold showers, no alcohol, nofap and building mental toughness).

My experience is my credibility and my activity within the app is public. Everyone can see that I’m not some hermit, who lived in a cave for 10 years, just a normal guy who quit porn and alcohol, which is precisely what I can help people with – and not much else.

But as coach John Wooden said: Do not let what you cannot do interfere with what you can do.
As an online coach, I’m judged much more by the quality of my questions, rather than my answers. Which brings me to point 2.

2. Anyone can be a top online coach

A couple months into the project, Tony did an interview with the top coach.

250 coaches were rated by churn rate. Churn rate is the probability that a client will cancel on a given day.

Josh Roman was 1.5 times more likely to keep a client than the average coach.

Josh keeps his clients, Josh gets interviewed, simple as that.

Astonishing as it may sound, Josh is by no means a professional coach.

He is the CTO at Koko FitClub, a digital gym company using technology instead of trainers. He is an entrepreneur, husband and father. Professional coach? I couldn’t find that in his bio.

So how did Josh kick so much ass? Turns out some simple strategies, which Josh developed as he went along, helped him surpass 249 other coaches, of which quite a few are professionals and make a living this way.

The key elements of his coaching are:

  1. Do a thorough initial survey to collect as much information as you can while the client’s motivation is high.
  2. Be positive and authentic – encourage your client and share your own story.
  3. Check in daily, even if clients don’t respond.
  4. Listen and ask – repeat information to make sure you both understand and ask questions to help your client focus on the right thing.
  5. Categorize clients, at least a little.

Putting his strategy in one sentence, Josh said to be “humble in giving advice and confident in asking questions”.

When I started out, knowing there were many other coaches, and seeing all the professionals getting featured, I remember thinking: “How in the world am I supposed to make it to the top?”

But those 5 things didn’t seem that hard to do. Read through them again. Do you think you could do those?

I bet you could.

Just following these 5 tips, putting in the work, keeping up with what’s new and implementing the suggestions from the coach.me team, I eventually got featured in March.

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Tony sends out a newsletter once a week, where coaches are featured, often offering the first week of their coaching for free. Which brings me to point 3.

3. Anyone can afford an online coach

At the end of February I created a 7 day video course that shows you how to leave your comfort zone. I launched it as a plan on coach.me, which caught the team’s attention and resulted in me being featured.

You can view the newsletter they sent out here (and find out the promo code for a free week of coaching with me).

After that the coaching is priced at $14.99/week.

I can already hear you ranting right now. “$14.99 for an online chat? Don’t you think that’s too steep? It is JUST a chat, after all!”

2 points to consider:

First, at $15 a week, the coaching costs about $2 per day. A “Grande Caffe Latte” at Starbucks is $3.65. Go figure.

Would you give up half a cup of coffee a day to finally be able to quit alcohol, reach inbox zero, lose 20 pounds or run 3 times a week?

Just think about how much money you spend each day, and whether you could cut that amount by $2. I’m sure you can find something.

This doesn’t even account for all the money you save when succeeding, such as money NOT spend on beers, magic weight or sleeping pills, or, well, coffee.

Second, I know my average message length quite possibly exceeds the norm, but my messages are always at least a paragraph long. My longest message is over 3,000 words – longer even than this post. More than once have I spent over 5 hours coaching on a single day.

Getting daily encouragement, feedback, advice and accountability from another human being, tailored to your goals and needs, isn’t that worth 2 bucks a day?

You be the judge.

Assess the potential of those 2 dollars – once invested in coffee, burgers, fast food, video games, alcohol, soda, cigarettes or gum and once invested in an online coach.

300 days from now, where would you be? Which brings me to point 4.

4. To succeed at long-term habits, let your willpower follow a bell curve

One of the primary things I learned when first consciously deciding to kick a bad habit (February 2013: nail biting, which I had done for the past 10 years) is this:

It takes willpower. A lot of it.

I remember the first day of not biting my nails. My hands were shaking and every 10 seconds I had to catch myself to not do it. In class. At home. On the bus. Everywhere.

It was a nightmare.

I couldn’t focus on anything else.

Eventually I made it through. It got a little better the second day. Then the third, and fourth, and so on.

Using lots of willpower worked out in this case, because I was in college and had enough time to focus on the habit and not much else (except showing up to class).

But guess what: When you have a job, meetings, a partner, social obligations, family events, kids and your own problems to take care of, that won’t do.

Willpower is a depleting resource, so when you get home after a long, tiring day at work, your spouse yells at you, because you have forgotten to walk the dog and you find out your favorite show was canceled, that’s when you cave – and have that bag of chips you’re not supposed to. Or that beer. Or gin.

Or, you bite your nails.

I see this pattern with clients, again and again.

It’s the reason why quitting smoking is so hard and why 90% of all New Year’s resolutions are broken within the first week of the new year.

One of the lessons I learned during coaching and reading about habits, addresses exactly this problem.

Think of your willpower as a bell curve. Over the course of establishing a long-term habit, let’s say 365 days, your willpower should follow the progression of a classic bell curve.


This means in the beginning, when establishing your habit, you shouldn’t have to use your willpower.

Then, as you build momentum in your habit, you can face more temptations head on and resist them.

You are much less likely to have a drink after you haven’t had one in 100 days – you wouldn’t dare to break the chain and you have enough willpower to keep it up.

As you progress even further you’ll find the habit ingraining itself so deeply into your daily life, that it becomes part of your identity.

This is the ultimate goal. By then you won’t have to use any willpower, because you’re not “practicing” the habit any longer – it has become the new norm.

It’s the point where the bell curve eventually reaches zero again and you can redirect your willpower towards other habits.

I wish I had known this back in February 2013. I would have bought one of those nasty smelling gels to put on your finger nails or covered them in dirt. Make them so disgusting I wouldn’t even think about biting them.

Note: This actually makes my job harder because partially I coach building willpower. Try telling someone in order to learn something they have to not do it. Good times.

So how do you not use your willpower when starting a new habit?

Make decisions beforehand and use a replacement habit.

Let’s look at another vivid example: My NOBNOM challenge.

Today I am on my 137th day of NOBNOM. I am also on my 315th day of no alcohol.

Note: If you do the math, this spoils the fun of guessing which part of the challenge I failed when receiving Tony’s email.

I quit drinking in June 2014.

I was nearing the end of an internship with BMW in Munich. Yes, Munich means beer. And no, not just on weekends.

Before I would drink rarely, but heavily. In Munich it became marginally less, but all the more frequent.

Luckily, the girl organizing the Wednesday weekly intern meeting was a non-drinker.

She reminded me of a time where I would always volunteer to be the designated driver, have a good time at a club with friends, dance and still wake up 5 hours before everyone I had given a ride.

I decided to go cold turkey.

From then on, to make my overnight decision become reality, I picked one non-alcoholic drink, which I would have the entire night, way before a party even started.

Note: Orange juice is a great conversation starter, who knew.

I also replaced all the beers inside my fridge with protein shakes.

Pre-deciding lessens the amount of willpower you need drastically. By having already determined what I would drink, I never needed to make a decision in the very moment where the temptation to drink was greatest.

By replacing the beer in the fridge with protein shakes I replaced the habit of having an after-work-drink with having an after-work-out (ha!).

Of course these are only 2 strategies, and plenty of other factors were at play (for example public accountability – by telling all my friends I would quit they were sure to remind me, if they caught me in weak moments).

But making decisions early on and replacing the habit helped me reduce the need of willpower until I had built enough of it to resist on my own.

Now, after over 300 days of not drinking, I hardly consider it a challenge.

I establish myself as a non-drinker as soon as I meet new people and all it takes to decline offered drinks is a slight head shake or a polite “no, thanks”

Had I had myself as a coach back when trying to quit nail biting, this is what I would have told my former self.

Would I have spent 2 dollars a day to make it through my first month after not being able to quit nail biting for 10 years?

You bet.

Which strategies to use and how to implement them is different for everyone and part of being an online coach is to find out the best way to do this for each client. Which brings me to point 5.

5. Check yourself before you wreck yourself – know your habit tendency

Part of Josh’s successful coaching approach includes doing a thorough initial survey on clients and then categorizing them.

There are a million and one ways to group people, and just as many coaching methodologies to go with them.

The best approach I’ve come across when managing habits, is the habit tendency framework.

Gretchen Rubin, happiness researcher and bestselling author, made out 4 tendencies among people.

Depending on your response to outer and inner expectations, you should adjust your approach to developing habits.


On her blog Gretchen explains the 4 tendencies as follows:

  • Upholders respond readily to outer and inner expectations.
  • Questioners question all expectations; they’ll meet an expectation if they think it makes sense–essentially, they make all expectations into inner expectations.
  • Obligers meet outer expectations, but struggle to meet expectations they impose on themselves.
  • Rebels resist all expectations, outer and inner alike.

The reason I like this system so much is that it’s simple enough for everyone to understand. What’s more, finding out your tendency feels like a light bulb going off in your head.

After finding out I’m an upholder, many things made sense in retrospect. It explains why it’s possible for me to establish or quit habits from one day to the next – as with my nail biting or my drinking. This is also the reason why I’m obsessed with finding rules, tend to overanalyze and sometimes end up paralyzed and don’t take action.

Knowing my tendency has also helped me understand why I coach the way I coach, with lots of quotes, calls to action and encouragement.

I now often ask clients to take Gretchen’s quiz, to better adjust the coaching to their needs.

But as the ancient Greek saying goes: Know thyself. Start out with learning about your own habit tendency.

An online coach is supposed to provide external accountability to the client. Yet this is hardly a one-way street, as I find coaching multiple people, for example in not drinking alcohol, is quite the accountability push for me to keep the habit as well.

Learning I am an upholder has helped me stick to my guns – and habits – and therefore helps me improve my online coaching.

Note: Out of all people interested in online coaching, the vast majority are obligers. It makes sense, as they are the ones, who respond best to outer expectations. This matches with the intention of hiring an online coach: Creating an additional source of external accountability.

What now?

Now you might say: “Nik, this is all fine and dandy, but what do you want me to do now?”

Don’t worry, I’ll tell you.

  1. Take Gretchen’s quiz and learn about your habit tendency.
  2. Download my cheat sheet below and use it to pick a habit you want to work on.
  3. Hire a coach to succeed at your habit.
  4. Sign up to become a coach.
  5. Follow Josh’s strategy and the coach.me team’s advice to become a top coach.


Thank me for showing you the best side job ever and maybe I’ll tell you how to get a free week of coaching with any coach on coach.me

Remember: Every step outside of your comfort zone is a step towards happiness.

Thank you Tony for prompting me to do so back in September. I don’t plan on going back.