An Email From My 93-Year-Old Grandfather

Believe it or not, my 93-year-old grandfather uses email … and Skype.

A few days ago, we had a Cambodia-to-California Skype session, in which I updated him on my travels throughout Southeast Asia. Then, he wrote me this charming, funny and heartfelt email:


I found last night’s conversation fascinating. On reflection, I have some comments for you, which are observations only and not intended to be advice or Solomon-like wisdom.

A very bright and extremely articulate young man graduated from San Diego State University as a journalism major. At that point, he was a bit cocky, turned down a lowly corporate offer, and was determined to venture into the emerging field of social media marketing.

With a family connection, he convinced a businessman to utilize his talents, and henceforth he was consumed by the Internet and its possibilities. On moving to Israel for personal reasons, he discovered that he could generate clients and income by living anywhere.

Having responsibilities to himself only, he could now travel and still carry on his business. His base of interesting clients and revenues increased, and he obviously possessed a growing talent in social media marketing.

However, for unknown reasons, he was dissatisfied with his situation, pulled up stakes and set on a journey to reset his clock, find more meaning in his life and establish some goals.

In the meantime, this young man has been attempting to develop a consultancy for freelancers, and for several months has been issuing free challenging newsletters to persons in his database and through the various online platforms.

To what extent these have been successful is unknown. The thrust of the message is that, as a result of his own experience as a successful freelancer, he can help other freelancers earn at least $100 per hour, get and retain worthy clients and live a completely location-independent lifestyle.

For some months, you have been on a journey of discovery of both yourself and your goals, which as of yesterday brought you to some town in Southern Cambodia. With your talent, I have to assume that you are still capable of generating enough income to sustain you indefinitely as a digital nomad.

Taking a leaf from some of your previous communications to prospective clients, such as there is never a right time to make a decision, or nothing is to be gained by procrastinating, is it possible that such advice also applies to you?

In any event, three obvious options come to mind:

  1. Continue being a digital nomad
  2. Establish roots somewhere, get married, have children. Even though you profess no need for material gratification, nevertheless this situation requires a certain level of reliable income. This in turn may necessitate considerable effort to achieve and obviously negates the first option.
  3. Marry a wealthy princess

Josh, whatever path you choose, you will still have my love and affection. I wish only a fulfilling life for you.

So, why am I showing you this email from grandfather?

Because we all have direct and indirect pressures from our family and friends, our peers, our cultures, and the societies in which we live. Notions like “freelancing” and being “location-independent” rarely occurred to people 20, 30 or 40 years ago, so it can be difficult for many people to understand the purpose of these lifestyles.

That’s why I bolded the part in which my grandfather said:

“There is never a right time to make a decision, or nothing is to be gained by procrastinating.”

While I can understand why my grandfather thinks I am procrastinating life’s hard decisions by freelancing and living a location-independent lifestyle, I prefer to defer to J. R. R. Tolkien, who said:

“Not all who wander are lost.”

A version of this post originally appeared on

Epic Freelancing is the go-to resource for freelancers who want to achieve financial success, creative freedom and lifestyle design.

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