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9 Lessons on Starting a Coaching Business

Are you wondering how to become a coach? Are you ready to be of service to other humans in their struggle to create a rewarding and meaningful life?

When I first started my coaching business, I made a pact: I will make this business work or I will die trying.

I’d probably been watching Braveheart or something and gotten myself all worked up. Later, after a few deep breaths and some time to think, I slightly adjusted my commitment and agreed that I would give it at least 5 years before I decided whether it was too hard.

Today marks the 5 year due date. And I’m still here.

As I do every year when I somehow make it to another anniversary, I’d like to share my insights and learning experiences.

1) BUSINESSES DON’T FAIL – PEOPLE GIVE UP

I’m glad I made that pact and commitment, because there were times were I really needed to remember it. Running your own coaching business is fucking hard. I’m never surprised by the failure-rate statistics of new start-ups.

5 years on, I’m stoked that I survived. I’ve bucked the trends for coaching businesses, most don’t make it past the 2-year mark. But you might be surprised at how close I’ve come to packing it in.

It’s not the business itself that’s hard. In a sense, with the right marketing and committed effort, anything can create a successful coaching business (I know of one guy who makes a decent living from just staring silently at people from a stage).

What’s hard is the sheer confusion, failure and rejection that you must face every single week.

When you bust your arse trying to make something helpful that serves others, it’s all too easy to become attached to outcomes, which means you crash when things go wrong. And, in a coaching business, they often go wrong (at least for the first few years). It’s mostly trial and error.

Sometimes I would just have too many failures in a row for my ego to handle and I would seriously consider giving up. But I stuck in there.

I’ve learned the recipe to avoid giving up is threefold.

Firstly, you must start a business that you would do for free (if you didn’t need the money). It must be internally satisfying if you hope to get through the hard times.

Secondly, you must accept and receive support, be it financial (e.g. loans), emotional or educational. You will not succeed on your own; stubborn independence simply delays your progress.

Thirdly, you must always be trying to serve, not to gain. If you try to do what is best for your clients, you’ll give them what they need, and you’ll listen to their feedback and improve rapidly. If you’re just trying to get paid, you’ll get lost down rabbit-holes of quick-fix bullshit and lose the respect of your community.

2) SEEK TO SERVE

Unlike trade industries like mechanical engineering, bricklaying and plumbing, no-one needs coaching. In fact, I believe it’s unethical to even suggest that someone does.

I know my clients don’t need to work with me, in that they can survive without me and do things on their own. My business is essentially a luxury item – it’s for people who want to massively accelerate what they’re already doing on their own.

There are no guaranteed clients in my work. I can’t just post ads and wait for phone calls. People rarely even actively search for coaching support (though they will often look for therapy, which is different). Few people even understand what coaching is, and those who do still have mental barriers preventing them from receiving support or guidance.

For me to find people to work with, I must search for those who are actively working on issues I can help with (particularly people-pleasing and Nice Guy Syndrome) and add value to their lives. I must help them before they pay for anything.

I’ve had to train myself to let go of getting. My neediness for money, approval, and even to have a positive impact must be put aside in order to truly serve. Not serve as in be a slave; not serve as in try to change other people’s lives; but serve my own integrity through trying to express the most powerful truth I can.

So I create content. I’ve written two books (The Legendary Life and Nothing to Lose) and have another on the way. I run a weekly podcast. I pump out video rants every other day. I write blog posts. And when I coach, I focus on being as honest as possible, even if it means pissing off my clients.

While I’m savvy enough with marketing to add my contact details to each piece of content, nothing I create is designed to get me anything. It’s all simply a release of what I hope will be a helpful piece of my truth. Ironically, the more truthful I try to be, the better response I get from future clients.

3) DON’T DO IT FOR THE MONEY

Most of the work I do is unpaid. Every week I create hours of content and have a bunch of first-time coaching sessions without a single dollar being created directly from this effort. Because of this, I must have a better reason to be in business than to make money.

This I believe to be a blessing in disguise. The people who don’t make it in the coaching industry will often claim it was financial problems that bought them down, but that’s bullshit. In reality, they gave up because they were primarily in it for the money. Being short on cash wouldn’t put a true coach off their calling.

Coaching is something I would still do for free after I inherited a million bucks. Helping people unblock their potential and start really fucking living for the first time is so incredibly satisfactory, so important to me, that it feels more like a duty than a job.

Ironically, that first ridiculous pact I made about ‘make it work or die trying’ is more realistic to me these days. I couldn’t go back to chasing money again, it would destroy me on the inside. To finally find work that is meaningful every fucking day must be incredibly rare, and I’m beyond lucky to have discovered it for myself.

Money is worthless compared to meaning.

But you have to feed yourself and your loved ones, right? That’s where coaching is tricky. You must charge for your services, and strangely you need to charge quite a lot. It costs more to work with me than it does to hire a lawyer. I’m yet to find a better way to qualify clients.

It took me a long time to get my head around this. Not only was the Imposter Syndrome constantly haranguing me for not being worth what I charge, but the most bizarre thing was that when I charged low rates or discounted prices, I ended up with low quality clients a lot of the time.

4) PHILOSOPHY IS THE KEY TO EVERYTHING

One thing I’ve learned after 5 years of trying to help people solve what look like impossible barriers is that the “how to” problem doesn’t exist.

What I mean by this is that when someone says “I don’t know how to do it” as if that’s the reason they’re stuck, you should not be fooled by this. Not knowing how to do something is the easiest problem in the world to solve. Hell, there’s a billion YouTube videos on every practical solution you could ever need.

Coaching is not about teaching someone how to do something.

The real issue people have is not knowing WHY they do something. They don’t have a philosophy of their own that guides them through the inevitable hard times and roadblocks. Anything is possible when you have a strong philosophy, yet most of the people I meet in this line of work barely even know what that word means.

When I say philosophy, I don’t mean subscribing to someone else’s, like Stoicism or Buddhism, though you can certainly find helpful direction from others. To me, helping someone discover philosophy means helping them design principles about why they should do something, by their own standards, which weirdly enough also helps them figure out what to do and how to do it.

These days, my coaching work is strongly focused on the WHY. I explore people’s morality, ethics and most importantly values, to help them figure out the meaning behind their actions. In short, I help them figure out who they are, underneath the performance they put on for the rest of the world.

And this of course applies to me personally. I coach because it’s a great way to live by my WHY – truthfulness, courage, compassion, determination – and for no other reason.

If other people are helped by my coaching that’s awesome, I love it, but that’s not actually why I do it. This is the main reason I’ve survived so far – I do coaching for me.

5) THERE IS NOTHING BETTER THAN CREATING A COMMUNITY

“If you want to go fast, go alone; if you want to go far, go together.” – African Proverb

Brojo is by far the most interesting thing I’ve ever done with my life. When Mike Wells and I first started it, we just wanted a place to chat with other dudes about self-development.

Now, it’s become a haven for people who want to explore philosophy, social confidence and self-development in a safe environment surrounded by like-minded peers and sympathetic allies.

Humans are a communal animal and we thrive best in groups. I’ve learned that independence is far less effective than resourcefulness, which usually means teaming up with people who compensate for your weaknesses and enhance your strengths.

I highly recommend anyone starting a coaching business put at least 50% of their effort into creating a tribe of people who support each other. It’s rewarding to watch it grow, and the most rewarding part is seeing guys who struggled to find friends in the outside world suddenly connect with each other within the community.

6) IF NO ONE HATES YOU, YOU’RE DOING IT WRONG

One of the toughest battles I had in becoming a coach was to face hateful feedback. This is not the same as helpful criticism or debate – I’ve always relished that. No, in preparing to become a coach the last thing I expected was to be personally hated for my ideas and work, especially because my aim is to help people.

What I’ve learned is that no matter your intentions, there are some people out there who will despise you for it. My first ever media experience led to an article that criticized me personally.

Most of them are irrational – they hate you because they misunderstood your point, or projected painful memories of their past onto you, or because they see you as some sort of threat for no reason. After exploring a few of my haters I found out they were just crazy, and not to be taken seriously at all.

But there are a few who will understand you correctly and hate you simply because they stand for the opposite of what you believe in. I’ve even met people who think developing yourself is some sort of evil. These ones are tough to take, because they sometimes actively try to sabotage you.

When I first got started, this didn’t happen very often. It escalated as the business grew. I came to realise the connection: as time went on I became more assertive, bold and polarizing with my perspective. I went from trying to please/help everyone to trying to express the truth, no matter what others thought of it. The more truthful I try to be, the more some people hate me for it.

It’s just a cost of being in this game. But it takes time to get used to it. It’s hard to see someone hate you personally simply because you suggested an idea to help someone have a higher quality of life. It’s simple enough to deal with people who just disagree with a point you’re making. It’s when someone compares you to a pedophile in terms of how harmful they think you are that it gets to you.

Some days I find it hard to accept, and I want to scream at people “What’s wrong with you?! How can you be against someone helping others? Live and let live motherfucker!”

But then I remember; in their eyes, I’m not helpful. So I should shift my focus away from them, and look for more of those people who I can help.

7) BEWARE OF ECHO CHAMBERS

Few things annoy me more in the coaching industry than seeing wannabe guru’s and “thought leaders” wank on about having found the one true way to live. They promise happiness and success and abundance, as if they have control over other people’s fate. No ethical coach should promise any results beyond delivery of a service.

Too many coaches get stuck in echo-chambers, where they and their community just continually agree on a single system of living and never challenge it. Anyone who speaks against their ideas is cast as an enemy, while anyone who agrees with them – no matter how evil they are – is welcomed as a friend.

In my own coaching and within Brojo, I constantly try to prove myself wrong. I pull out beliefs I’ve held for years and ask people to poke holes in them. I’ll even listen to the haters if they’re at least making coherent counter-arguments.

When you’re a coach, you must walk a fine line. You must be confident enough in your views to assertively and shamelessly help someone – what Rich Litvin calls fearless coaching – yet you must also remain flexible enough in your psychology to change based on better evidence and reasoning.

It’s a constant battle between ego and truth, one I must fight every day.

8) BALANCE IS MOST NEEDED WHEN YOU LEAST WANT IT

The biggest lesson I’ve learned after being at this for a while is that it’s a marathon, not a sprint.

At the beginning there’s a lot of sprinting – setting up websites, contacting hundreds of leads, racing from one event to another – and it’s easy to get stuck in this pattern.

5 years later, you need to slow down or you’ll burn out. These days I try my best to maintain a balance.

When I started, I was doing up to 80 hours per week, now I’m down to about 30. I prioritise things like having lunch with my girlfriend and learning to speak Czech with the same status as my work.

Being a coach means living what you preach. Too many coaches are massively hypocritical – constantly telling their clients to live more balanced lives while they themselves practice poor habits and time-management.

If your clients have better lives than you from taking your advice, something’s not right.

9) DON’T DO IT!!

My last lesson is a simple one: if you’re not sure about becoming a coach, then don’t do it.

You don’t need to be sure of “success” or knowing how to run a business, but you need to be sure of your passion for this work. Because you will be tested beyond measure. It will hurt more than you predict, and you’ll have to face every fear and insecurity you know you have, as well as many others that you’ve never even awakened before.

You will be financially insecure for much longer than you’re prepared for. You will have some people negatively affected by your attempts to help them. You will fail and be rejected far more than you’ll win and succeed. Every problem you solve only creates two more.

If that’s worth being a coach, then you’re ready.

If you’re ready to pay that price, then you absolutely should give it a go. This industry is rife with coaches who should not be coaches – people looking to apply some pseudo-psychology and anecdotal experiences to interfere with someone else’s life, just to make a buck. We need better coaches to push these charlatans out, and provide a service that everyone can enjoy.

No-one needs a coach, but everyone can benefit from coaching.

4 Responses

  1. Glad you’re made it out for 5 years bro. You helped me a lot, and I’m sure for so many others…so I think that’s why.

    Keep it up and I’m think you will, because again, you do it for you, right? 😉

    1. Certainly have my selfish reasons that keep me going 😉 Cheers for your continued support dude

  2. Congratulations on hitting your 5 year milestone Dan. We’re all beneficiaries of your fortitude and persistence.

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