Part 3: $40,000 on Coaches, WTF?

Welcome to a multi-part series on creating my first online course. Check out Part 2 here.

I can confidently say that RadReads is finding its rhythm. The blog and newsletter have found a comfortable cadence and together act as a flywheel for a budding coaching practice and speaking gigs. And while these are high-value “exchanges” of time for money (aka revenue), they are not sufficient to cover our annual burn. While we’re smart about money and investing, we’re NOT a FIRE family; most of our expenses come from prioritizing travel, physical activities, and experiences. And another big one: coaching. Specifically, $40,000 of coaching.

Yet another coach?

Launching the digital course led me to hire a second coach. Yup, you heard that right – someone who could specifically help me get over the impostor syndrome of launching a new venture. But first, let’s backtrack: $40,000? Over 5 years? You’ve got to be kidding me!

I hired my first coach in 2014, one year before leaving Wall Street. I had already made up my mind that I was going to leave, but felt like I needed an emotional safety net to keep me grounded during the entire process. Along the way, I began confronting my scarcity mindset and fear of death – while building the confidence to step outside of society’s expectations of what a “successful career” looked like.

Next, I wanted to do some deeper emotional excavation and began a series of conversations around suffering, delayed gratification, religion, cultural norms, love, and the after-life with a second coach. And recently, I added a business coach to the roster – bringing my four year spending on coaching to approximately $40,000 (or $10,000 a year).

Can it possibly be worth it?

There’s a huge body of research that spending money to buy back time is one of the best investments you can make – and this includes experts like nutritionists, personal trainers, and coaches. That’s a highly personal question, but for me it’s a resounding hell yeah. For starters, it’s hard to quantify the confidence that arises when you confront your biggest fears and insecurities: you take more risks, find contentment in life’s mundaneness, shed your envy and stop caring about what others think. How on earth could you ascribe a dollar value to that?

But with the course, I found myself battling another set of obstacles. The vagueness and open-ended nature of a big, new project. The lack of a playbook. And tbh, just the lack of confidence to getting started.

Starting has never been one of my weak spots

I’ve got the knack for starting creative projects – unafraid of the consequences of failure. Create, and they will come. But as I wrote in the prior post, the perception of being a snake oil salesman was holding me back:

My greatest insecurity about RadReads (and, by extension, this course) is to be perceived as a fraud. A hedge fund huckster who lures unsuspecting readers into the false promise of a happier and more fulfilled life. I’m always wondering if I’m naive to the fact that everything I write about is of limited value – or even worse, it’s dangerous thinking.


The clock don’t lie

And I could see this fallout from this insecurity when I conducted a time audit. “Research and development” as I was calling it was dead fucking last on the spectrum of activities. For someone who knows how to focus and is well organized, I knew that this was a symptom of a bigger problem.

And I saw this in my behavior. I was so overwhelmed about where to begin, that instead of putting one foot forward, I would just look for an easy release – like checking email (where I spent 4x more time).

Finding “Important, not Urgent” accountability

My coaching practice has given me a firsthand perspective on how hard it is for solopreneurs to tackle the Important, Not Urgent bucket of the Eisenhower Box. I know that one of the reasons they engage me is quite simple: every two weeks, I’ll ask “Hey, did you make progress on that long-term project?” Sounds simple, but despite being the highest leverage activities – we tend to avoid them.

And tbh, I just needed someone like that in my own life; not to mention someone who had experience in course design, pricing, digital marketing, and the dozens of other things I knew very little about.

But $40k, you’re nuts man?!?!

I am steadfast in my belief that I will always have a coach. It’s the highest leverage investment in myself, my marriage, and my business. Yes, I cringe every time I send over the PayPals – but my life is filled with daily reminders of the dividends. And they too, compound with time!

Join us on May 2nd for our digital workshop: The Fulfilling Path to Financial Independence, which includes:


  • A two hour live virtual workshop on Financial Independence (with full replay access)
  • A live Q&A with Khe Hy with ability to submit questions in advance
  • activation templates to start planning your path to Fulfilled Financial Independence
  • Lifetime access to the curriculum and modules
  • Private invitation to the Financial Independence Slack Channel
  • Discounts on all upcoming courses and workshops


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