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When faced with a difficult decision, find an easier one

Hi, I’m Josh Katz

Peak Enjoyment is my life + business coaching service for emotional, self-reflective, analytical guys age 20-40 who want to develop a means of entrepreneurial income generation that they deeply connect and thrive with while improving their relationships & health, and while being the most supportive version of themselves they can be for the people they care about.

If that’s something you connect with, I would love to hear from you.

A few of my favorite Personality Traits






Banff National Park, Alberta, 2018

My Process

I believe the process of navigating through a desire for major change benefits greatly from a one small step at a time approach, and one that integrates holistic health reflection. It’s tough though, small steps can seem meaningless and big steps seem overwhelming and high risk. And who has time for new wellness routines when they’re deeply consumed by an overwhelming sense of desire for something different on top of everyday life? My goal is to help identify, design and track small steps that seem deeply meaningful and guide high value wellness interventions in super manageable and fun ways, together which I find accelerate the journey over the long term in totally wild ways. It’s hard to imagine how good feeling good is going to feel, and it’s usually a lot closer than we think.

In my experience, periods of existential reflection and change seeking often touch one or more of the following realms. Part of my process is to reflect on and engage all of these holistically, at the appropriate time. I believe it’s hard to truly enjoy contentedness in one of these without pursuing contentedness in all of these.

How we make our money

I find most deep change journeys start or center here, triggered by a growing or longstanding awareness of a dissatisfaction with how we spend our time and who we spend it with, in relation to how we make our money. That makes sense to me, because it’s largely what we spend most our time doing.

Whether it’s accelerating progress towards an already identified alternative, or figuring out where to go, I find once we believe we can get there, it’s just a matter of taking small steps and enjoying the process.

Our primary relationships

Once any kind of existentially motivated or deep change journey begins, I think we naturally almost always end up evaluating all of the close relationships in our lives. Especially if this is our first time going through something like this.

I think experiencing deeply mutually positive, supportive and loving relationships of any type is both itself a path to peak enjoyment, and also super critical to achieving change in the other realms.

Our health & wellness

I maintain a personal health & wellness framework that engages nutrition, fitness, sleep, emotional health, and deep personal organization. I think real long term change that sticks is totally possible and can actually be easy and fun. I think it’s all about identifying top value action items, approaching them in ways that are natural and fun, and pursuing change slowly and one step at a time.

General existential perspective

I think its absolutely critical to peak enjoyment to engage in existential reflection and perspective development. That said it can be a dangerous place to hang out.

My goal is to help channel and direct that highly valuable reflectiveness into low stakes experimentation and life change activities, and to steer it away from self-reinforcing deep dark spirals.

Deciding isn’t knowing

I think radical change and transformation can be good some times. But also I feel that even more so, slow, gradual, long term change is much better. I like to say change is good, but as long as change is happening, the less change the better. Now that’s a little semantic because there is some optimal middle ground, but for me it’s definitely not changing a bunch of things really quickly. I think one great way to tell if the pace is too quick is if you find yourself making a lot of decisions. Making decisions often means you’re doing things that aren’t coming naturally, because all day every day we instinctually do things without even thinking about them.

So I like to say, When faced with a hard decision, don’t make it, find an easier one. Because deciding isn’t knowing. As a coach, I like to help people uncover things they already know, to move more naturally and intuitively. I think realistically this accelerates change and enjoyment over the long term because there’s less change in direction. While it often means moving slower in the short term, I think it’s simply more enjoyable and practical that way. So in the framework of peak enjoyment, its the only real option.

If you’re feeling recurring or sustained stress inside our coaching work, I think we’re doing something wrong.

PILOT Program – Free Coaching Available

As part of my launch of this new coaching service I am offering a free 4-week coaching package for up to 10 approved clients.

Program Highlights

Up to 4 free weekly coaching sessions @ 60 minutes each

Additional 4 weeks of additional coaching at a 50% discounted rate at $75/hour

Sessions conducted by video conference on Sunday or Monday between 10am-4pm

Currently accepting applications until January 16th, 2024

You can email me at with any questions or to begin the process