Your Choice: Start a Business, or Fail at Personal Freedom

Let’s assume you like money, and living well, and also having time to do what you want to do.

Fair? I think I’ve cast a wide net.

Pretty much everyone wants this. We all want to live the 4 hour workweek, but the mechanics of what he describes in the book are heavily dependent on getting paid for results, not your time.

Which doesn’t fit most “jobs” i.e. typical employer relationships.

For that reason, you have only a few choices as I see it:

  1. Be born wealthy. Statistically speaking, there’s a 99% chance this is not your lot in life.
  2. Work in “Service Asymmetry”, i.e. pro athlete, movie star, very popular musician, in which millions or billions consume your product and thus you get paid very handsomely, can have a very short career and amass wealth quickly. Statistically, most people won’t succeed (or even try) at this. Most pro athletes end up broke anyway due to spending habits.
  3. Rapid asset accumulation, combined with high ROI, relative to your standard of living. If you live super cheap, make $130k/yr, save $70k/yr after taxes, then you could retire after just a few years… this doesn’t work if you make $60k, save $10k/yr – it simply follows the conventional gold watch plan (retire after 35 – 40 yrs of work). Statistically, most people won’t earn this kind of income AND keep their expenses low enough to make this work- $130k/yr is good income, but most people’s lifestyle pretty quickly rises to match as they follow the house / mortgage / kid / car pattern. Your goal here is your passive residual income exceeding your lifestyle expenses (burn rate liftoff – i.e. making $10k/mo/net rental income or investment yield with expenses < $10k/mo)
  4. Build a business and be successful at it. That 2nd one is a kicker, but if you have a day job wherein you get paid for time, this seems to be your only logical choice as I see it. Am I wrong? Comment below. Fortunately, the internet has created as many opportunities as hazards, and turbulent times favor upstarts not incumbents. Easier said than done, I know, but fortunately, new ways of thinking about this can drastically lower your risk and cost to get moving – i.e. the lean startup or pivoting from service to product.
  5. Redefine your employer relationship to get paid for metrics and results, not your time. For some, this will work – sales professionals for example, but for the majority, their job descriptions are probably too complex for their employer to actually accept this. Besides, automation favors the business owner, not you, so over time, they get more results for less of your time, and can then load you up with more tasks – so like it or hate it, the business owner has a financial incentive for you to stay hourly in most cases, then systematically optimize your workflows (while they reap the benefits, not you).

When just a child I loved robots.

I was born in ’75, so the early 80’s was a time of industrial automation, and fears over automaking robotics, bold claims for the future, and Tang. The inevitable future to my 8 year old logic was that some employer would own a fully robotic factory, and get all the money, while paying fewer and fewer employees. The first plant to go fully robotic would enjoy wider profit margins, affording more robots, outspending on R&D + advertising, and ultimately make the best company and dominate the market.

I was an odd kid. But am I wrong?

The market domination would then lead to an arms race, in which most of the humans would get displaced by the most cost-efficient production method, and while price competition would thin margins over time, the damage would already be done to the workforce.

So this is our world, like it or not. The real question becomes then, what side do you want to be on?

If you can’t beat ’em, join ’em. So I became a robot.

Ok, so that’s a joke for my wife – but I did side with employers and had similar concerns over the classic labor vs. capital power struggle (summed up nicely by friend Max: “What struggle? Capital won.”), which is why I’ve always bootstrapped. The good news: there’s never been a better time to bootstrap and start a business part time on the side, then grow the income to replace your day job – so you truly can live the 4 hour workweek if you choose.

The 1 Hour CEO

I’m CEO, but only for 1 hour per week.

This all started a few weeks ago, when I was feeling pretty overwhelmed. I’ll spare you the humblebragging claims to busy-ness, but  that day in particular had significant demands on my time, each with serious repercussions if not filled.

So, I stepped back for a few minutes and blocked out my time, for the week, and it provided a sense of relief.

It freed me up to NOT do 99% of my
workload at that moment.

As a small  business owner, I wear a lot of hats. All small business owners do, and the process of growing your company means progressively giving those hats away. If you do your job correctly, you’ll be left at the end of the day with no hats, but still having a profitable company.

This is also the easiest type of company to sell – one that doesn’t really depend on it’s owner / founder. Until one gets to this point, I maintain one hasn’t truly built a company, but has simply built a “practice” or a job.

Anyway, by blocking out my week into chunks, including top-level sales, marketing, customer service, HR, and even specifically scheduling personal time to work out and get some sunshine, Dad time with my son, “float time” for catch-up and interruptions, it provided me clarity, because I then had license on what I should _not_ be doing at any moment.

As Paul Graham pointed out what many knew instinctively but hadn’t fully carved out, “maker time” requires deeper thinking, and without license to block out the world, I wouldn’t get anything meaningful done.

To implement this yourself, try a David Allen style Brain Dump, categorize it into the hats required of you, figure out about how much time per week you need on average, include some “slip time” each day (like office hours for college profs), and block it out.


  • List of hats common in small business / tech startups is below
  • Include time to be a human, and some fun time regardless of how motivated you are. For you tech startup Type A people: Engineer for your own limits. I have about 70 hours a week blocked, but some of that is for being a father, husband, exercise, sunshine, personal admin (i.e. home improvements, taxes, etc.) – so actual worked hours is really only about 45-50… crazy work weeks aren’t sustainable long term without cost – my record is 104/hrs week (7x 14 hr days actual work), but it was frankly sort of stupid: I ended up not working at my highest and best use, so working hard was actually inferior to working smart even on a pure results basis, not just life-enjoyment basis, not to mention “wife? what wife?” basis. Tim Ferriss’ awesome 4 hour workweek is a reminder of doing just what matters and delegating the rest.
  • Polyphasic sleep is awesome if you can swing it socially. I average “everyman” or siesta during the week, then monophasic or segmented or siesta on weekends, depending mostly on parties and my social planner’s schedule (wife Lidia Ryan)

Roles – just a sketch here to get you started.. your week consists of…

  1. HR // team-building, retention, management
  2. being CEO // the big picture decisions, implementation in overview, raising funds if not bootstrapping, monthly reports, etc.
  3. Operations // aka “the product” for tech startups. This is a big one for me, as we’re mostly into product-market fit still. As we hone this, things like growth hacking get more important – til then, it’s water in a leaky sieve.
  4. Marketing // I break this out into outbound, inbound, traffic, and The Offer i.e. CRO
  5. Sales // getting the $, blend of this varies by your business…
  6. Accounting // even if you delegate, you need to know these numbers as CEO.
  7. Customer Support. // I talk to real-world clients every day and think it’s essential to startups, but that’s opinion.
  8. Food: I cook a lot, and find it meditative. I solve big code problems while cooking, and it’s fun to work on something physical.
  9. Exercise. Skip this, and you’ll regret it sooner or later.
  10. “office hours” – free time to deal with slipping deadlines, interruptions, calls that weren’t planned, etc.
  11. Personal admin – laundry, etc.
  12. “Sharpening the saw” – even if just a few minutes per week (tip: overlap with exercise via audiobooks), this is worth it.