ENT(601) – The Canvas Strategy: Helping yourself by helping others.


Welcome back to the weekly reflection series. In this post, I am continuing the discussion of strategies, recommendations, and advice Ryan Holiday provided in his book. Thus far I have introduced three different concepts revolving around the character development any successful entrepreneur should be aware of and manage to the best of their ability; the ego, passion, and the purpose. As reflected in the title of this post, the topic for today is the canvas strategy.

I think it would be beneficial to define what exactly the “canvas strategy” is, as Holiday defined it. In summary, the canvas strategy is a process of helping yourself by helping others and trading your short term effort for a longer-term payoff.

In this segment of the book, as it has been the trend in the past, Holiday introduces several examples of successful implementation of the canvas strategy. One that intrigued me the most is the story of Benjamin Franklin, the famous printer, writer, statesmen, inventor, and of course one of the founding fathers of our great country. 

When Franklin was nine years old, his father decided to pull him out of the ministry prep school as he could no longer afford his education. Instead, Ben was tasked with working as a helping hand in his father’s shop. In the years to come, Ben educated himself, whenever he could find the time, from books that he was able to buy or borrow from others. When Ben was twelve years old, realizing his potential and love for books, his father apprenticed him to his eldest brother James, the printer. James later founded and began publishing The New England Courant, only the second newspaper in America (Nelson 2005).

At sixteen years old, Ben wanted so badly to have one of his works published in his brother’s newspaper but he knew his brother would object. Ben needed a masterplan. He decided to start writing letters under a pseudonym of Silence Dogood (Holiday 2016). For years Ben would write the letters, slide them under the print-shop door, and watch them get printed on the front page of The New England Courant while receiving no credit for them. Ben, or should we say Mrs. Dogood, continued writing such letters for the following six months, totaling sixteen letters, before disappearing. By then Mrs. Dogood completely charmed Boston (Nelson 2005). 

However, the loss of such a valuable correspondent affected the newspaper tremendously and left the readers greatly distraught to the point that James ran an ad in his paper looking for anyone who can identify Mrs. Dogood, to which Ben responded to and finally revealed his secret to his older brother (Nelson 2005). The reveal did not work out well for Ben (at first) as his brother was greatly upset with him; however, in the long run, Ben knew his strategy would work in his favor. 

During the time serving as his brother’s apprentice, Ben learned how public opinion worked, generating awareness of what he believed in, crafting his style, tone, and wit (Holiday 2016). Ben saw a long term benefit in making other people look good by taking his ideas as their own. He was not upset or impatient. Rather, he was waiting for the perfect moment to reap the benefits of his master plan.

Upon breaking the apprenticeship with his brother due to ill-feeling and rivalry, Ben moved from Boston to Philadelphia and within few years set up his own press and began publishing the Pennsylvania Gazette, one of the United States most prominent newspapers – considered to be the New York Times of the 18th century (Hanney & Lester). According to Accessible Archives, The Pennsylvania Gazette was established in 1728 and ceased to exist in 1800 (Hanney & Lester). From this example, we can see how the eight years of his life Ben sacrificed in the shadows of his brother and behind a pseudonym led him to become one of the greatest and most influential figures in the United States History.

We can further conclude that, as Holiday stated, “greatness comes from humble beginnings; it comes from grunt work. It means you’re the least important person in the room – until you change that with results” (Holiday 2016).

In conclusion, as aspiring entrepreneurs, we should not shy away from opportunities that may seem useless or demeaning. We should evaluate each opportunity with caution and create bonds and relationships in the process. It is not easy but it is doable. It requires a lot of self-discipline and control over the ego. The canvas strategy has no expiration date and is one of the few that age does not limit. You can start at any time, young or old, employed or not, starting something new or finding your place inside of an organization (Holiday 2016). 

I’ll end with a quote:

“If you pick up this mantle once, you’ll see what most people’s egos prevent them from appreciating; the person who clears the path ultimately controls its direction, just as the canvas shapes the painting” – Ryan Holiday


“The Pennsylvania Gazette 1728-1800.” Edited by Iris L. Hanney and Robert Lester, The Pennsylvania Gazette 1728-1800, Accessible Archives Inc, www.accessible-archives.com/collections/the-pennsylvania-gazette/.

“Benjamin Franklin Introduces ‘Silence Dogood.’” Edited by Liz Nelson, Benjamin Franklin Introduces “Silence Dogood”, Mass Moments, 2005, www.massmoments.org/moment-details/benjamin-franklin-introduces-silence-dogood.html.

Holiday, Ryan. Ego Is the Enemy. Portfolio, Penguin, 2016.


  1. Semir,
    I really enjoyed reading your post. That is an interesting story. It just goes to prove the importance of having a group of people on your side. The hard part is achieving that positive public opinion. I think about a leader in an organization that might lead by title compared to creatively gaining support amongst the masses in the organization. But I wonder what would have happened if nobody believed Ben Franklin?

  2. Semir,
    That is a true statement, we must be able to help ourselves through the use of helping others. Just as with the story of Ben and his brother, Ben wanted to have his work published in his brothers news paper and he knew that would be impossible. However, Ben did not settle and found a way around that particular obstacle. Through finding a way around his obstacle he was able to write his work which not only benefited himself, but benefited his brother as well even though it was not acceptable. Ben went on to become successful in the end. It goes to show that as entrepreneurs we must learn how to adapt in order to achieve our goals and be able to help others regardless if they are willing to return the favor. You’re right, to become successful we must he self-disciplined. Great post!

  3. Semir,
    You’ve touched on some very important points. As both an entrepreneur and a leader it is imperative to check ones ego at the door. It it beneficial not to despise humble beginnings or small opportunities as they could bring about great outcomes. As you stated, this notion is one that does not expire. It also should not be limited to solely the entrepreneur. As a leader, entrepreneurs should welcome this behavior and mindset among employees and partners. It creates great learning opportunities for everyone. Great post!

  4. Semir,
    You’ve touched on some great points. It’s imperative as both an entrepreneur and a leader to check ones’ ego at the door. Entrepreneurs should not despise circumstances that may not seem ideal or mirror what they imagined. These situations can bring about the most profound change and experiential growth. This practice should not be limited to entrepreneurs. As a leader, entrepreneurs should encourage their partners and employees to embrace difficulties and make the most of the situation. This teaching moments can be beneficial for everyone. Great post!

  5. Semir,
    I really enjoy your post, In the act of struggle, an entrepreneur must be rugged in finding solutions and way out of difficult situations, be it to create it or conjure the solutions. The mind of an entrepreneur is like a fertile land that needs cultivating, the tenacity to cultivate and not give up will yield harvest on the long run. Great post!
    Bolanle Akinyemi

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