Cowboys and Indians: The Two Types of Entrepreneurs

Josh Hoffman
Epic Freelancing
Published in
3 min readJun 1, 2016

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Credit: Strength Weekly

In my experience of being an international social media and content marketing consultant since 2012, and advising freelancers as part of Epic Freelancing, I’ve come to realize that there are two types of entrepreneurs: those who want to make as much money as possible, and those who want to create a career around their life — what Tim Ferriss calls “lifestyle design” — as opposed to creating a life around their career.

For the sake of brevity, we’ll call the first group Cowboys, and the second one Indians.

Cowboys are all about the “hustle” and a “win at all costs” approach, even if those costs entail minimal work-life balance. They work hard and smart. Some might call them workaholics. When Cowboys aren’t actually putting in the work, they’re thinking about it nonstop.

Indians, on the other hand, would rather spend as much time as possible away from work, exploiting their hobbies, spending time with family and friends, adventuring, sleeping, or whatever it is that tickles their fancy — so long as they’re bringing in enough money to afford the lifestyle they desire. Indians may work hard, but they mostly focus on working smart, always in search of the latest hacks to optimize time efficiency at work.

As with most instances of apples and oranges, Cowboys are no greater or lesser than Indians. They’re simply two different paths to the same destination: happiness. In fact, many people start out as Cowboys and make a conscious decision to become Indians, and vice versa, over time. “Once a Cowboy (or Indian), always a Cowboy (or Indian)” doesn’t apply.

However, an issue arises when entrepreneurs or wannabe entrepreneurs don’t take the time to fundamentally understand if they want to be a Cowboy or an Indian before embarking on their entrepreneurial journey; they start a business with hopes of being a Cowboy, but eventually realize the business they started is more in line with being an Indian. Or, they think they want to be a Cowboy (or Indian), only to realize down the line that they’re more suited to be an Indian (or Cowboy).

Therefore, the keys to succeeding as both a Cowboy and an Indian are:

  1. Using self-awareness — also known as being “real” with yourself — to understand which type of entrepreneur fits your personality, mentality, attitude and habits, and then
  2. Creating a business model that aligns with your inner Cowboy or Indian

Regardless if you elect to become a Cowboy or an Indian, the entrepreneurs who understand their end-game before saddling up will give themselves a significantly better chance of riding off into the sunset.

Epic Freelancing is the go-to resource for freelancers who want to develop a six-figure income and live life on their terms.

Get the free guide “6 Steps to 6-Figure Freelancing” >>

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Founder of IZZY – Stream Israel, basketball lover, mental health advocate