Confessions, Cautionary Tales & Case Studies

The Personal Blog of the Undaunted Hustler

Opinions so new, they may not even be mine yet. 
I blog about business, family, & goals. 
When I'm out of willpower, I talk politics

Breaking The Browser Habit

Breaking The Browser Habit

The browser vexes me.

On my Mac, it’s a portal to whatever the world has to offer. It’s mostly distractions.  Things that don’t benefit me, support my goals or put me in position to be of service.

I use it a lot – because I’m not a luddite: I use the Gmail App.  I compose in Google Docs.

I’m writing this – right now – in WordPress.

Problem is that with those of us that use shortcut keys a world of distractions are just a CMD-T away. (New Tab, Facebook.  New Tab, Sporting News. New Tab, Twitter.)

This is an attack on Deep Work and on Focus

So the goal now is to use the browser sparingly, only for vital things.


Focus Is A Muscle

Focus Is A Muscle

It’s hard to focus. It’s always been hard for me to sustain concentration over a long period of time. The human condition. I’m not unique, and I may even be above average. Still. It’s the biggest challenge, and mastering it creates a reward.

The muscle muscle be built.

Spending time in the Flow State, serving your business, serving clients, serving others.  That life. That night.

The digital age. The million distractions that we can respond to. The opportunities to slide.

Working to get *good* at focus by the following means:

1. Tools- Things like IA Writer, notecards, timers, standing desks- that make it easy to think through and complete tasks.
2. Schedule- A plan in advance what we are meaning to do. We set alarms so that it happens.
3. Friction Reduction- There are loads of opportunities
4. Systems- Templates to do things “correctly,” so that every time we work on something we aren’t reinventing the wheel.
5. Checklists- A subset of tools, but we want to always know what we’re working on.
6. Virtues & Practices- bigger reasons that we do what we do. This sort of comes last, but is also first.

Being personally competent is a first order value. Like with the thoughts on “debt,” if there is a lack of personal control, then it’s going to be very hard to perform in an open ended job.

GTD was a triage system that helped us work through and “churn digital widgets.” But we want to make a life that supports the type of focus and deep work that transcends triage.


Other Types Of Debt

Other Types Of Debt

For close to 6 years I’ve been running a company called Simplifilm. For four years I had a (great) partner. We’ve had some accomplishments. The creation and sale of a product. Best selling authors worked with us. More.

We also pushed a bunch of stuff under the rug. Both in the “partner days” and beyond. They put our company in peril, and took some of the *joie de vivre* out of running our business.

From our friends in tech we understand the concept of Technical Debt. This is when you don’t address the underlying problems with technology and patch software that may not be written correctly. By not embracing current methods, we rely on old fashioned methods. Or by kludging things together this is what happens.

In *The Hard Thing About Hard Things*, Ben Horowitz talks about *Management Debt.* He may have introduced that idea. Management debt is when you put off hard decisions and create a rotten culture. An example would be to give people raises when they brought offer letters. This would train people to always be seeking offers.

I’ll say that there were several types of debt that we incurred:

Administrative Debt

This comes from things like not having a rigorous file structure, not having a setup so we can easily recall information and a system for working internally and externally. Not doing 1 on 1s.

When you just “put something in a Google Drive” in lieu of having a time to name files and organize things correctly. You pay this off when you need something and have to spend time searching for it.

We also find ourselves reinventing the wheel frequently. How, where do we market?

We didn’t have a method to catch issues, a standing meeting or something that would cover relationship, strategy, marketing or anything else. So there was a void and assumptions never got clarified. Nobody was accountable for this stuff.

Strategic Debt

This is the sort of thing that Verne Harnish’s work covers. Having a strategy **and** a method to review, renew and change your strategy. We were “just making videos.” We didn’t have anything that would inform decisions about pricing, about what types of clients we’d take. We just wanted be in the flow. Again, because I can close and Jason could design we got away without really having a strategy.

We also had different ideas as to what we should be. He wanted to be a little, elite boutique (a Ferrari). I wanted to be a higher volume shop (Toyota). We never really reconciled ourselves to that so we were both working from different assumptions, and that could have been resolved.

We were fundamentally working from different assumptions. And because *a lot* was going right, we never took the time to see where we were at with things.

Relationship Debt

My partner is a hardworking and honest guy. I try to be. We had some relationship issues though. All people will. That’s humanity.

All people will mess up, all people will. I know I have.

We’d have issues that would come up – a milestone date would get blown, or poor communication would lead to having to rework some art. Those things will happen in any business that has human beings involved. We’d both grouse at one another but we’d never really create a system to understand, empathize and support one another.

A poor journey on my end would make me seethe but I’d say “No big deal, I can always earn another sale.” Both ideas were totally true. *From a certain point of view.  But the issue really was that the resentment built. The sense of futility.

What happens though is without really solving the issues, you build debris in your relationships.  And that creates a long term problem.

Financial Debt

This is the debt that most of us consider to be the most important debt. When we started, we made some errors in incorporating. We were growing unevenly so we punted on things like “how we’re going to pay ourselves.” We ran for a year as an LLC and then a C-Corp.

We had to pay ourselves high salaries. Me because I was paying for my wife’s school. Jason because we were 50/50. This meant that we took money out of the company that could have been spent on building up the company. Because we had other stuff going on (and no structure to resolve it) it hurt us.

We surfed the payables and then things crept up on us slowly. Money wasn’t there to take care of things. We’d get by with a new batch of sales.

Our growth obscured it – in absolute terms the lag between payroll and the rest was severe. But relative to what we had it kept shrinking.

Marketing Debt

This is all about lead generation. We never built systems to consistently generate leads.

SEO was a skill I employed successfully in our early days, and then we had a great flow of past clients. But we never really addressed “where do we get new leads.” This is a subset of strategy. We just didn’t agree on how much of our time this would take.

An example was that we only made 1 :30 second video for ourselves when we worked together. Because we didn’t have other things get resolved.

Another is that there was nothing other than fairly manual ways to acquire customers.

Cleaning Up The Balance Sheet

This isn’t the only type of debt that exists. Fitness debt, mental hygiene debts are all real things that really do exist.

All of the above added up to some situations we’d not do over the same way. Had we to do it over again, we’d have done it differently for sure.

Now, we’ve been more successful than not. But the “bad stuff” or punted choices threatens to hurt us. It was always there, in the back, restricting our growth.

Taking a toll on my very sanity.

The waiter brought the bill. We have to wash dishes for a while. But we’ve got a business that can make it all work.

Curriculum March 2016

Curriculum March 2016

In March, I’m committed to getting back to reading and exercise. I’ve got a big hill to climb and I’ve imperiled my company by having had so much overhead.  That lead to a place where we were behind on deliverables, and started a death spiral that (I hope) we’ve pulled out of.

The idea is to return to the “flow state” that exists.


  • THE POWER OF HABIT: This is well written, I’ll finish, but it’s lighter on specifics than I hoped it would be.  It’s foundational material, in lieu of usable material.
  • Booked Josh Turner: I need to get back into the flow where I was constantly generating great leads for my business.  I’ve been out for a while.
  • The 12 Week Year: Brian Moran
  • Influence by Robert B. Cialdini
  • Titan by Ron Chernow- This is one that I started in December, so I’ll be able to get through it. It’s longer but I need to know about the period.
  • EGO IS THE ENEMY by Ryan Holiday  (this book isn’t out yet, but the always-loyal ryan has agreed to get me a copy).
  • Javelin Rain: Myke Cole (the reward for finishing Titan).  A sci fi book by a friend and author that is just crushing it.
Making The Worst

Making The Worst

Many of the big problems in my life aren’t times when I made the worst of a bad situation.  I was probably more right than wrong at the outset, but…the reaction was graceless.

A few things I would do differently

A few things I would do differently

  1. Don’t change your cell phone number (unless it’s to disconnect from people.)
  2. Don’t allow (many) inbound calls.
  3. Add 6x more value than what you take away.
  4. Don’t be snarky.
  5. Be nicer to family.
  6. Stay in shape.
  7. Get in shape to begin with.



Deep Work – Cal Newport

Deep Work by Cal Newport is an amazing book that will certainly change my life.  The process is going, and I’m excited about where it will take me. It’s a book that I can’t really criticize because it’s so good

As something of a workaholic, I’ve had spurts where additional hours not only no longer produce value, but undo work I’ve done.  A case in point is the current state of the Simplifilm website.   I have done, undone, and redone it dozens of times and I’m not substantively closer to being OK. It’s consumed hours and yielded little extra benefit.

That’s because I’ve worked while distracted, while unfocused, and this means that the work suffers.  A little focus – at the expense of other things – is the way to go.

But Deep Work truly is at the expense of other things. If we are to make an amazing contribution we have to “drain the shallows.”

The book is divided into two parts: one “the case for Deep Work,” and two “How to Work Deeply (which also spends about half its time reinforcing the case for Deep Work).

The first part is for motivation. We learn why this matters, we learn how peer-reviewed academic journals have treated topics like concentration, performance and mental throughput.  (Beginners can practice a musical instrument for about an hour a day. Masters can rarely go past 4 hours.)

The main gist is that Deep Work is rare.

In Part II, we’re given more specifics. We’re given definitions and exhortations.

-work deeply (create habits that support it)

-quit social media

-drain the shallows

-have a quitting time (so you can go back)

-embrace boredom (which means that you can’t scratch the itch all the time to do things.

This book has started a curriculum for me of things that I’ve meant to catch up on.  I finished Scott Adam’s new book : How To Fail at Almost Everything and Still Win Big. That book compliments this one. In that it provides an example/case study of a person who has optimized his life to work deeply.

The case for deep work is compelling. It’s our chance to in fact make a contribution that lasts longer than we do. It’s done through deep work, not merely getting better at “cranking widgets,” which has diminishing returns.

I’ve optimized my life to be able to be more productive. I’m working from home again, and I’ve got my things about me.  It’s time to make a big contribution.


Connected To The Stream

Connected To The Stream

There’s a feeling when you are connected and working in flow that really feels good and works well.  You’re sharper because you’re connected to the stream.

That is like flow but different.  Because you’re studying and working hard (for me reading, writing, all my life) you are the best version of yourself.  Because of that, you have opportunities that are often not available to you.

That’s how winning works.

Batching Work

Batching Work

Reading Deep Work by Cal Newport.  One of the ideas that I want to do more of is to batch work and that is something that I haven’t done a tremendous job with yet.

Hopefully in lieu of trying to dabble at a little of everything I can have the guts to go deep and bold.

I am, I suspect, too connected for my own good at the moment, and it’s impacting my ability to do deep work, which impacts other things as well.

Ruby’s Journal

Ruby’s Journal

Has a journal. Currently, in her journal are nothing but memories of what her friend from Portland are like.  So she doesn’t forget them.

Unfinished Business

By Christopher Johnson | October 14, 2018

I left Real Estate in 2008. In something of a huff, with the confident contempt that I’d never be back. Good riddance, we said to one another at the time. I had done all the jobs in the industry, pretty much. The last one had me as a mortgage lender, and I was waiting out […]

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By Christopher Johnson | October 12, 2018

One of the things I love about the current economy is its opportunity. People can be anything, do anything. The thing I hate? There are so many people that achieve a tiny modicum of success, they are one chapter ahead in the book, and they then stop practicing. They start teaching. A couple exceptions would […]

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By Christopher Johnson | October 10, 2018

Not too long ago, my friend Tim Paige was musing on Facebook about people with dual careers. Dual Careers by choice, and not because they were beginners. Tim comes from over in Voice Over, and there are a lot of people that do that gig part time. Or they do it while also pursuing something […]

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Hustle as Performance Art.

By Christopher Johnson | September 20, 2018

(Really cool poster by Joey Roth) Most people don’t hustle. Sturgeon’s Law and all that. The big blue ocean is too big and scary for them, and they seek the familiar. I’ve been that guy way way more than I’d like to admit. Like me, most people think they hustle. It’s comforting to think that […]

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Notes On Hamilton

By Christopher Johnson | August 28, 2018

While Heather and I were driving around the PNW for a really great little 5-day vacation, we listened to Hamilton a few times. I have been listening to the choruses for a long time, but I never had the chance to REALLY listen. But man, oh man! This work was genius. The density of the […]

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To Be In Practice

By Christopher Johnson | August 15, 2018

One of the things about opening up a business is that you need to find your way to what you want to do. In my case, I’ve missed out on being a practitioner of sales for a few years. Thinking back, it’s been over three years since I’ve really sold with the idea that maximizing […]

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Dear Microsoft:

By Christopher Johnson | July 24, 2018

Dear Microsoft: Listen, I am rooting for you. I love me a good comeback story, and it seems that you are dialed in right now. And I’m glad. But, look, you’ve got to respect me a little bit more. I have two of your products: Office 360 and Xbox One. And they both annoy me […]

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The Muse Vs. The Practice

By Christopher Johnson | July 19, 2018

We’ve all had those moments where we can work effortlessly. Where it “comes.” Our creative output is remarkable. The Muse visits. They happen. It’s a thing. We’re right to embrace those days. We’re right to feel proud and good of being in the flow and producing something great. Emrace anything that helps. The beginner, though, believes these […]

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That Old Familiar Fear

By Christopher Johnson | July 7, 2018

For the last year, I’ve been winding down Simplifilm. I’ve got this idea about what I did right, which was getting clients for agencies. I love to sell, I love to hunt and I love to help. So I put a little site together with the intentions of launching something on Monday. At Simplifilm I […]

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Daily Operating System: A Theory To Practice

By Christopher Johnson | June 24, 2018

Days have gotten away from me, and I’ve not accomplished enough in 2018. My decision velocity is sluggish, as has been the output/throughput. For those of you nice people like David Gibbons that are telling me I’m too hard on myself, I say to you “meh.” I’m not, trust me, I’m not. Time Freedom is […]

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