I'm Failing As An Entrepreneur
2 min read

I'm Failing As An Entrepreneur

You won't get rich renting out your time. This concept is repeated in every book about business, entrepreneurship, and financial success.

And still, instead of taking a leap of faith to embody these essential truths of entrepreneurship, I find myself more likely to reach for Another Book, hoping it will reveal a secret loophole to success.

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The three most harmful addictions are heroin, carbohydrates, and a monthly salary. - Nassim Taleb 

My name is Jamie, and I might be addicted to a semi-regular paycheck.

I'm generally comfortable with financial risk:

  • I've earned an income freelancing far longer than I've collected fixed paychecks
  • If a client can no longer work within the conditions that allow me to produce my best work, I typically part ways as soon as possible  
  • I optimize my work life towards my lifestyle instead of optimizing my lifestyle to my work. In practical terms, this means I don't work anywhere near 40 hrs/week

I'm proud of what I've achieved working online, evolving from a curious writer producing keyword stuffed articles for SEO marketers, to writing email copy that makes me laugh for trendy ecommerce brands. The number next to the dollar sign on my invoices has grown along with my confidence and ability, but still I find myself unsatisfied.

Given the choice between doubling my freelancing income, or adding a much smaller income stream that has no direct correlation to the amount of time it steals from my weekday—I'd choose the latter.

In my ideal reality, my income is primarily derived from the results of yesterday. Jack Butcher would call this Build Once, Sell Twice.    

I knew about this concept before discovering Jack Butcher. This same idea has been repackaged dozens of times in tweets, books, and blog posts. Jack Butcher. Naval Ravikant. Nat Eliason. Daniel Vassallo. Ryan Kulp.  I've read them all and still I've yet to make meaningful progress towards a reality where my income is a result of my past concentrated efforts.  

What I've realized too late is that this failure to create can't be traced back to lacking knowledge. Somewhere along the way I became addicted to consuming information about the outcomes I want to achieve instead of making efforts to create them for myself.  But information was never the bottleneck.

Training, upskilling, and learning are all essential parts of growth, but they won't propel you any closer to your goals if you already knew how to make progress prior to entering your credit card on Gumroad for Yet Another Course.  

I believe there are 3 reasons why I've failed to achieve my goals:

  1. Making money freelancing is way easier, and more certain
  2. I'm scared of wasting too much time on uncertain returns
  3. I'm not entirely convinced I'm capable of doing it, causing me to consume more information as a sense of security

At the end of the day, maybe I'm better suited as a great freelancer or a high performing employee. I don't know just yet. What I do know is that I'm growing impatient waiting to find out.