workaholic digital nomadImagine for a moment that you quit your office job several months ago in order to start a business. Within six months, you’ve got more clients or customers than you know what to do with and the profits from your new venture exceed what you used to make at your 9 to 5 job.

It sounds like an easy recipe for relaxation, complete with Mai Tais on the beach and days filled with leisure activities in some exotic location, right?

Well, perhaps, but just because some successful lifestyle design guru makes it look easy, the truth is that they probably work more than most people who hold a traditional job. More on that point later.

One reason why people gravitate to the idea of starting a lifestyle business, as opposed to working for someone else, is that they believe it will allow them to spend their time as they like. However, there is a dirty little secret about many successful digital entrepreneurs: their lifestyle business is often more of a business lifestyle.

The truth: Lifestyle businesses are not built overnight

Digital entrepreneurs are some of the busiest people I know, compulsively checking email, working on their website(s), thinking strategically about how to scale/pivot/disrupt/exploit, networking, and generally hustling for more business. What started out as an experiment to improve their quality of life while earning a healthy income, often descends into workaholism. I should know, because I speak from experience.

Those slick videos and podcasts they do on a regular basis require HOURS of preparation and process refinement. Even if they outsource the technical bits of their digital presence to their team, the online entrepreneur still has to put together a script, set up and research guests, come up with topics to discuss, do some quality control to ensure the final product aligns with their image or brand, and so on.

In short, they don’t just roll out of bed and land in a pile of money.

It is easy to romanticize the notion of being self-employed, but there is a cost to success few talk about. Wantrepreneurs (those who aspire to entrepreneurship) often look at people at the top and assume they can do the same thing, but what they don’t realize is that many of these people have put in tons of hard work to get where they are.

  1. Tim Ferriss started BrainQUICKEN in 2001, but only became known after The 4-Hour Workweek was published in 2007, after being rejected by 26 publishers.
  2. Pat Flynn was laid off in 2008 and first started making money via AdSense and selling advertising space on his blog. He then launched an ebook and podcast.
  3. John Lee Dumas left his job and lived off savings while working 12hrs/day learning how to podcast and recording scores of interviews. The cash only came later.
  4. Gary Vaynerchuk worked for his family’s wine business and recorded 1,000 episodes of Wine Library TV  starting in 2006. Three years later he got a book deal.
  5. Dan Andrews & Ian Schoen first started their entrepreneurial journey in 2007, and didn’t release their now-successful podcast until 2009.

The point is that many of the household names in the lifestyle design / digital entrepreneur / passive income space put in a boatload of effort to get where they are today. The key to their success is a combination of serving an untapped market, personality, money management, living below their means, developing multiple streams of income, mastering one or more media channels, and outsourcing low-level tasks.

They might make it look easy, but trust me, none of the top people in this space work four hours per week. Moreover, many of them are so tied-in with their brand that it would be nearly impossible to conceive of an exit strategy that wouldn’t also involve the demise of their current business model.

So if you aspire to be an online entrepreneur, be prepared to put in the time and effort required. Even then, there’s no guarantee that you’ll be recognized for the savvy businessperson you are. This is why, for some people, the best way to financial independence involves working for someone else. That may be tough to hear, but it is true, because search engine results are overflowing with personal blogs that never get any traction, that make no money and that are loaded with good content that barely anyone ever reads.

Be realistic about growing your online business

The reality is that building a lifestyle business means that you will have to work hard, at least in the initial stages while you grow your business. Telling from the examples above, when you hit the big time, you work more, not less: speaking engagements, book deals, angel investing, product development, interviews, etc. Even then, sometimes hard work isn’t enough.

If you aspire to run a business by spending only a couple hours a day working, that’s great, but this decision is usually a conscious compromise in favor of free time and flexibility at the expense of scalability.

While this is not always the case, because I’m sure there are outliers, my feeling is that anyone starting down this path ought to manage expectations, think clearly about what it is they hope to attain, and develop a system that will allow them to scale as much as possible without putting in more time.

Questions for reflection

  1. What are three ways you can scale your business? Will it involve new technology? Does it mean hiring more employees?
  2. If you wanted to sell your business now, would it be possible for someone to take it over or is it so tied-in with your name that you will always need to be involved?
  3. Who do you most admire in the location independent / lifestyle design / podcasting space? Why do you think that most of the big names in this space seem to be working so much? Does that undermine their message or is just inevitable that popularity makes new demands?
  4. How do you understand the difference between lifestyle business and entrepreneurship?


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