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Is Becoming a Coach Worth It?

It’s hard to be a good coach. If you want to be a mediocre, sort of ok, minimum wage coach, that’s much less hard. There are literally thousands of books and courses on how to be an ok coach. 

But to be good, to be great, that’s hard. So before you take the leap, make the investment, and quit your day job, ask yourself, “Is becoming a coach worth it?”

You can only really answer this question yourself, but I’m going to do my best to help you figure this out before you get too far down this path. 


#1 Do you love people?  Are you also driven mad by them?

When I first wrote this, I typed, Do you enjoy helping people? But then I realized too many coaches get started because they like “helping” people. Except what they call helping people is really just telling people what to do.  

Most advice isn’t followed and it’s also not asked for. So changing someone is rarely about getting them to do something different. It’s about helping them discover what they really want. 

To be a great coach you have to love people. You have to love them even though they make stupid choices over and over again, you have to love them even when they get mad at you for telling you the truth, and you have to love them even when they are really whiney about something they can easily change. 

If you love people, becoming a coach might be worth it. If you just like telling people what to do, then work for TSA. 


#2 Are you curious?

Some people like being right and some people love being curious. Some people love both. 

Most great coaches I know love being right, but they love being curious even more. Curiosity has an element of humility to it. A willingness to be wrong and to not know. 

Even great coaches are wrong a lot, often they don’t realize it at the time and neither do their clients, but as we shift people, we do so from a series of guesses, distinctions, and explorations. 

Like working through a maze, there are a fair amount of dead ends. There are less as you get better but there are dead ends nonetheless. 

So you need to be curious and you need to long for curiosity more than you long for being right. If you need to be right, coaching will become about your ego and agenda. Sure some people will love that and you may find success, but that doesn’t mean you’ll find mastery. 


#3 Can you sell? Are you willing to learn?

Great coaches sell. They get clients to sign up. They do this in conversations and online. Great coaches simply learn how to get people to commit to change and then hiring them to create the change. 

Selling isn’t as mysterious or evil as you think it is. It can actually be enjoyable. But if you think selling is evil and you hate the idea of asking someone to pay you, you might be better off having a job where you sell once during the interview and collect a paycheck for years. 

If you sort of enjoy talking people into things or helping people get to yes then becoming a coach is worth it, if not you may want to do something else. 


#4 Do you really want to do meaningful work?

This may seem obvious, I assure you, it’s not. People say they want to do meaningful work, but they really don’t. They don’t like the pressure, the significance, or the depth of commitment meaningful work requires. 

You may prefer to have some lightness in your life, to keep things simple, or to not actually say your work is about changing lives. And that’s ok. 

Meaningful work sounds great on paper but what it asks of you is harder. It asks you to put your life, your ego, and your heart on the line. 

If you do meaningful work, you’ll be disappointed. You’ll wonder if it’s ever enough. You’ll work hard to change someone’s life and they won’t change. You’ll have to let go, let them be on their path, and trust that they will find their way. 

So be honest with yourself if you’re really up to this or not. 


So is becoming a coach worth it? 

For me it’s never been a choice. Once coaching found me, it hasn’t let me go. 

It’s magic. You get on the phone. You talk to someone. And their lives change. 

Recently a client of mine finally settled her divorce after years of strife around it. 

Another client got the promotion at work she had wanted for a long time and started enjoying her life more than ever before, she even let herself be fully committed to her amazing boyfriend for the first time. 

Another client repaired a relationship with a major client he was sure was at its end. All in the midst of the client getting some tough medical news. 

To me that’s magic. To me, all the things that are hard about being a coach are worth it, because of who I get to be for people. 

But it isn’t easy, it takes work, commitment, and guidance from a master to get great. 

So if it’s not worth it to you, choose something else. You can always be a great listener for your friends in between shifts at your amazing startup job or tell lots of people what to do at the airport while they are going through security.

Being a coach isn’t a ticket to freedom, but it IS a ticket to an incredible life, if you decide it’s worth it for you. 


Stop Asking “How?”

90% of the questions I get from coaches is about how to do something. 


How do I price myself? 

How do I find clients? 

How do I sell better? 

How do I get better as a coach? 

How do I feel more confident? 

How do I handle it when they say they can’t afford it, when they don’t return my calls, when they want to quit?


The list is nearly endless. 

In some ways, “How do I…?”, is not a bad question. You need to learn about the art of coaching and the art of enrollment. Being curious about how to do these things and how to get better isn’t bad, but it’s also not what gets in the way of 90% of coaches.


The question that really matters is are you DOING IT? 


Are you giving people your price? 

Are you out there trying to find clients, connecting with people, and making introductions? 

Are you selling or practicing selling your coaching? Or even selling a podcast to people who might like it? 

Are you working to improve your coaching? Getting feedback? Studying other coaches? HELL are you coaching anyone right now? Even someone for free? 

Are you doing things that lead to confidence? Exercise? Eating good food? Acknowledging yourself for the things you’ve done well? 

Are you thinking about ways to handle those things when they come up? Are you looking at how you did it in the last call and how you might do it in the next call? 


Most times coaches AREN’T DOING IT. They are sitting around trying to figure out HOW TO DO IT!!!! And again, how is a fine question to ask, but only after you do the first part. 


If you’re out there trying stuff out and learning, asking how questions can help, and of course when you’re VERY new and getting started, having some how, will make it easier for you to take risks. 


The real problem is the trap of always asking how, HOW HOW HOW, instead of saying ok. I have a way I can try, I’ve seen one option. It may be scary. I might mess up, but I’m going to try. 


Staying in HOW keeps you safe, and it gives you the illusion that some way, out there offers a way to try something without the risk, fear, and self doubt. 


Do yourself a favor. Go do it. Embrace the fear and self doubt. You’ll get stronger and you’ll actually learn WAY more than asking will ever reveal. 


Here are 4 ways you can get started:


1) If you’re not currently coaching anyone, get a free client – 

This isn’t hard, just go into any coaching group and offer your coaching for free. A lot of people will say not to do this. YES if you only do this it’s a trap, don’t get stuck here, but coaches coach people. If you ain’t coaching, you ain’t a coach. So go do a trade with another coach, or get a free client. Practice and learn with them. 


2) If you’re not getting paid, charge something –

Once you’ve worked with a couple of free clients then charge something. It can be a dollar, or two. It can be $100 or $1000, just charge something. Be willing to have the conversation about investing money in your work with someone. It will teach you a lot. Even if you are only charging a dollar. 


3) If you’re not charging enough, raise your rates –

Do it on the next call. Double them. Or add a zero to them. Whatever you do, raise them. You’ll have to step up and have a different conversation, you’ll get scared, the person may be more likely to say no, that’s ok, just try it out. Notice what happens when you charge more and learn from it. 


4) If you’re not working with a coach, HIRE ONE!!!

Or choose another profession. There are CRAZY amounts of coaches with no coach. You can’t do it, I mean you can, but it’s like coaching with your head up your ass. Having a coach means you’re getting pushed, it means your work matters, it means you matter. It will make you a better coach, it will have you be accountable. It doesn’t have to break the bank, (though investment does matter) but no matter what, just have a friggin coach. 


All of these are ways to be able to say YES to the question “Are you doing it?” 


And what’s amazing to me is that for most coaches when they simply start, they start making it. They build their career into something incredible, they get clients, and they turn pro. 


The how helps, don’t get me wrong, but it doesn’t change lives. 


So go look yourself in the mirror and ask yourself, “Am I doing it?” 

And if the answer is NO then get started. The world needs incredible coaches like you. 




Performance vs Morality

Performance is a function of performance. We offer certain inputs, inside a certain environment, and we see what kind of outputs we get. 

The more we can control for the environment the more we can predict and modulate our inputs to get a certain output. The more chaotic or seemingly random the environment the more performance becomes part art and part science. 

It’s easy to get lost in the dance that we ‘should’ know the correct inputs. 

We should have the right knowledge, experience, data, and courage to make the ‘right’ choices.  Only a future you really knows what the results of your choices are. 

From here, the future is a void. When we measure performance, observe the process, and are attentive to results we can generally perform better over time given the right resources. 

Morality is how good you are or a judgment about whether you are a good person. Because we value performance we often think that people who perform better are better people. It isn’t actually true, and very often we’re disappointed when star athletes, giants of industry, or our leaders reveal their human frailty to us. 

But because we value performance it’s easy to think that performance is the most important factor of morality. Even though it’s not. 

While thinking that performing better will make us better people might inspire us to work and pay attention, the utility of this mix up pretty much stops there. And for every person who seeks to perform better to be better, there are three people who feel awful about who they are because of some real or imagined lack of performance. 

In truth, these two things are just different. Not that they don’t interact and play with each other. But performance is performance. It’s a measure of outputs based on certain inputs in a certain environment. And morality is morality. It’s about who you choose to be in life, it’s about kindness and generosity, it’s about love. 

And anyone who’s ever tried to measure of tweak the utility of love through performance can probably tell you the futility of trying to bar graph the heart. 

If you can allow them to be separate. If you can survive poor performance while maintaining a good self-image, so much is possible for you. It takes work, but it’s a worthwhile path to follow if you wish to do meaningful work in the world. 

What does it mean to embody a great or masterful coach? 

I remember once standing in the lobby of a coaching event and a new coach came up to me and said someday I want to be a coach like you. What did they mean? I wondered to myself. 

Yet I get what he’s talking about. Within a few minutes of meeting a coach, I can often tell how I feel about them as a coach. Sometimes I get this wrong due to my own biases and filters, but often I get it right. And it’s not because I’m psychic or incredibly intuitive. 

There’s just something about a truly great coach. A way they hold themselves, a way they speak, a way they listen, even just the way you feel when you sit with them. 

This is the embodiment of a great coach. It can seem mysterious, but it really isn’t. 


What does it mean to embody a great or masterful coach? 

Anyone can call themselves a coach. Anyone can ask a few coaching questions. But there’s something that set’s some of the world’s best coaches apart. 

  • Creativity
  • Depth
  • Authenticity
  • Integrity
  • Commitment and the ability to help others commit 
  • Clarity with finances
  • Spirituality or relationship to the divine 
  • Purpose and vision
  • Professional ethics

I didn’t become a coach to get rich. There are easier ways. I became a coach to embody the spirit of someone who changes lives, my own first, and those of people I care about. 

Maybe you became a coach for this reason too. If so, stop focusing on the skills, the nuts and bolts. They matter, but the context of your focus matters more. 

Focus on embodying a great coach, focus on BEING a great coach. 

And in the process, you’ll learn everything you need to do and to know.

Anyone can call themselves a coach, anyone can ask some coaching questions. 

But being a great coach, even when you’re walking alone in the woods, or cooking dinner. 

That’s rare and really something worth working towards.

Poetry Can’t Get You Clients

A few months ago I started writing poetry.

In truth, I’ve been writing poetry all my life, in moments of contemplation, in moments of love, in moments of difficulty poetry, has always been something I’ve turned to.

And yet as I began to write it I had a thought. Who’s going to hire me because I write poetry?



Mostly in the past, I’ve written about leadership, about how to build a coaching business, about how to coach well, or how to live well.

Instead what was coming out of me was meditations on death, reflections on love, questions about what meaning there was to life, and what it’s like to go through pain and heartbreak.

I mean who wants a coach who talks about that stuff?

Don’t we all want a guide with the answers?

Don’t people LIKE my answers?

But on some level that didn’t matter.

I just had poetry pouring out of me. So that’s what I wrote. And because I’m committed to showing my work and being honest about who I am. I shared my poetry.



And then a funny thing happened. I got a referral from a former client. It wasn’t a direct referral. This client had a client who wanted to refer their boss to me. Someone very intelligent and powerful. Someone who ‘could win a Nobel prize in the next decade or so.’

On the call, this woman told me: “I’ve been reading your poetry and something about it gave me the feeling that you’d be the perfect person to coach my boss.”

HUH? I thought to myself.

Maybe poetry can get you clients.



The truth is people long to be themselves, without apology, without exceptions, without limitations.

As leaders and coaches, we can either pretend to be what we think people want to see (which is what is more common than not) or we can be ourselves. Both have the potential for attracting people.

Some people are looking for the illusion of perfection or excellence. Hoping to steal some of the perfect paint and paint it on themselves. But other people are looking to be themselves and if you are willing to be yourself, with courage, humility, and a little humor that will inspire them.

You can attract people using listicles and the answers, it might actually be easier.

Or you can attract people by being willing to be yourself.

The question is what do you want to rely on?

And what do you want to build your leadership and business on? 

My 3 Secrets to Winning the Coaching Adventure Game by Francesca Woltanski

Today we have a special post from our friend and fellow coach Francesca Woltanski. She highlights her experience with the Coaching Adventure Game and tells us how she won! Check it out below.Read more

Boundaries, Love, And Why I Blocked My Ex On Facebook Part 2

So why didn’t I trust her?


Sure there were moments where I thought she wasn’t fair to me. Sure, I worry about how she’ll paint our relationship when she talks about it, but generally, I experienced her as a kind and loving person. 


She cherished me and let me go. 

I wanted to cherish her and let her go as well. 


I realized that if I trusted her to take care of herself and to feel the love I had as I set my boundaries, there really wasn’t anything to be scared of. I could block her on Facebook, and she would figure out I did it because I loved her and myself. Because I trusted her to be at peace with my choice and what was right with me. 


And this is the 2nd lesson I learned about boundaries:




When you trust someone, to take care of themselves, to be with your no, to find peace inside themselves, to be complete, to love you, setting boundaries is easy. For most of my life, I didn’t’ set boundaries because I was afraid I’d be rejected and abandoned. 


I thought the fewer boundaries, the better. And when I did set boundaries, they often had a flavor of anger, push back, or spite. But this process has slowly taught me that offering a boundary to someone you care about, perhaps even without explanation, is one of the most powerful gestures of trust you can offer


In truth, I have no idea how my former partner will take me blocking her. It’s at least 6 months before we can connect again. She may have or be thinking all of the things I was scared of. She may not even notice I blocked her at all. 


But the choice felt right to me. 


I want to get back to where I can be truly happy for her. Where I can see her radiant on Facebook and be so grateful she shared that radiance with me. Where I can see her with someone else and know that she’s created new love in part from the lessons of love we learned from one another. 


I know my next partner will have a lot to thank her for. 


And I know that blocking her now. Allowing that little jolt to fade, giving myself the space to be alone, to find joy in solitude and singleness, will help me get there. 


I trust her. To walk her own path. And to find a way to honor the path we walked together. And I trust myself. To set boundaries and discover what those boundaries are here to teach me. 




My wish for you as you read this is that you find a way to practice with your own sacred boundaries. To offer them as a gift to those you love, even when they don’t totally understand, even when you don’t ‘think you need them.’ 


The practice of boundaries can be like this, not aggressive or aversive, but loving and kind in so many ways. 

You Don’t Need A More Productive Way To Produce Suffering

Dear Future Client,

You became a coach because you thought in some way it was the answer. Maybe at this point, you don’t even remember what the question was anymore.

For me, the question was about finding purpose in life, doing work that mattered, having a sense of freedom, and making enough money so my father would be proud of me. Despite the fact that he says he proud of me all the time. But I may be luckier than you in that.

And yet here you are, a few months or years into your coaching journey and you still haven’t arrived yet. Maybe you make the $10k months every Facebook group I get invited to raves about, or maybe you’re close, maybe you even make more than that.

And yet you haven’t arrived. You don’t feel free. You don’t feel successful. You keep looking over your own Facebook wall into someone else’s life who seems to have it sorted out. Maybe you even think I have it all sorted out.

You portray an image of success that covers over a subtle form of self-doubt. You don’t really know if you’re a good coach. You find yourself frustrated with your clients. Tired after a day of sessions. Feeling both free to do incredible work and trapped by the incredible work you do.

So you go out and hire someone to improve your deal flow, to get you more clients on linked in, promote your product to a broader audience, and help you with Facebook ads.

But the truth is you don’t need a more efficient way to produce suffering. You don’t need a better system to help you find again what you’ve already found.

Please stop hiring experts and gurus and people who have the answers.

Instead, it’s time to look at the very heart of why you suffer. To discover the parts of yourself you’ve stepped over on the way to success.

Sure I can help you get better at sales, sure I can help you figure out how to hire a better assistant, sure I can help you develop some basic systems to put your attention more on what you want to do.

But all of these things require you to let go of who you think you are as a coach and entrepreneur. They mean flying in the face of the scrappy do it yourself, figure it out, hire it out identity.

That’s something they never tell you about, the existential crises of being an entrepreneur.

So when you’re ready, I’m here. When you’re ready to let go of a more productive way to produce suffering and find the leader inside of you, the one who can create something truly unique to the world.

When you’re ready to stop looking for answers and find yourself instead.
I’d love to talk to you.

Not because I have any answers, but because I love looking.
With people who are committed to curiosity.


Boundaries, Love, And Why I Blocked My Ex On Facebook


Boundaries are the distance at which I can love you and me simultaneously. – Prentis Hemphi

Last week I decided to block my ex on Facebook.

She didn’t do anything wrong, she didn’t start dating someone else (or if she did I don’t know about it), and I’m not mad at her. I blocked her because I love her, and I love myself as well.

I’m going to my best to explain why I did it, what I learned about myself, and hopefully, you’ll learn something about how to love yourself and others in the process.

Read more

Things I Don’t Understand About My Coaching

There’s something compelling about reflecting on your work and what you’re creating with your life. You probably know the answers you always give at cocktail parties or events by heart, but if you dig deeper into the nature of your work, you may find things about it you don’t understand. In being with those questions, you may discover something totally new about your work and life that creates more wisdom and love. Read more