Building a Portfolio of Side Hustles
The Importance of Minimizing Failure, Developing Backup Plans, and Improving Your Skills
What can we learn from failure? I don’t know. A few years ago I thought I knew the answer. It usually went something along the following lines: failure is an important drive toward growth and success. You learn a lot by failing a lot.
Hold on, what's the point of repeatedly failing without making necessary adjustments toward a successful venture? If you continue to experience failure, how will you identify the potential causes and make improvements accordingly?
What if you don’t even know the reasons why you’re failing? Maybe you’re not good enough to carry out the project you have in mind. Would you continue to fail happily ever after?
Daniel Vassallo argues that failure doesn't always guarantee growth or success. Instead, focusing on small wins might be more effective in achieving better results. This is because small wins can serve as a better indicator of what is working in your ventures.
Psychologically, even a small win can boost your excitement about what you’re doing, potentially leading to better overall results.
While failure is a realistic possibility for any project we undertake, it is better to minimize the size of the failure and its impact on us - be it financial or professional - rather than adopting it as our "north star" and using it as a stepping stone towards success.
So can one learn from failure? Maybe, insofar as it’s minimal, and you remain afloat after the fact.
Take the case of Hassan Osman, whom I mentioned in a previous article, and with whom I recently had a great chat on my Marketplace Discussions podcast.
Hassan has managed to build his brand as the ‘on-the-side guy’. He writes books, records courses, and runs a podcast all while having a full-time job. He has several Amazon bestsellers, including ‘Influencing Virtual Teams,’ ‘Don’t Reply All,’ and most recently, ‘ChatGPT for Nonfiction Authors.’
Among Hassan’s target audience are busy managers, entrepreneurs, and full-time employees who are trying to create side hustles to generate multiple income streams.
On Udemy, over 290,000 students signed up for Hassan’s courses to date. Yes, you read that right, two hundred and ninety thousand students.
But it wasn’t all rainbows and sunshine for Hassan.
After graduating as a civil engineer, he pursued a master’s degree in information security policy and management. It was a new program in a field that was both new and growing.
Hassan's initial job was in tech consulting at EY (Ernst and Young in the past). On the first day of his job, after returning home, he opened his personal laptop and penned down the first words of what would become his debut book.
Although the book didn't sell well, it was a valuable learning experience that had limited downsides. At worst, the time invested in writing the book would have been lost.
But Hassan didn’t stop there. He took a leave of absence for six months to move to his home country, Lebanon, in order to work on a photojournalism magazine called ‘Sowar’ (Arabic for photographs).
The concept was straightforward: people enjoy viewing photographs but often don't have the patience to read the lengthy articles that accompany them.
Thus, the idea was born to produce a magazine that centered on a particular theme for each issue, featuring photographs captured by photojournalists that tell a unique story.
Hassan’s ‘Sowar’ project did not take off, he was losing money, magazine ads were being purchased at a huge discount by the businesses, and it was difficult to penetrate the market, so a few months later he abandoned the idea and went back to his job.
Although his first venture failed, Hassan had a backup plan. The valuable lesson he learned was that if he wanted to create multiple income streams, he needed to start small.
Rather than undertaking a venture while on an unpaid leave of absence, he decided it would be better to create products on the side.
Fast forward several years, Hassan’s portfolio of digital products has been doing well, with only one downside: time invested.
The upsides are infinite:
Books, courses, and podcasts can be a great way to establish credibility, gain exposure, and create a solid network and community.
In the case that they sell, that’s an extra income.
You build and sharpen a new set of transferable skills that might help you land a new job in case you lose your current one.
You feed your curiosity, learn, grow, iterate, and become better equipped for a world that is constantly changing.
Why bother creating a portfolio of side hustles?
I asked Hassan this question, and his response was clear: for two obvious reasons, represented by the carrot and the stick. On the one hand, having an additional income stream alongside your monthly salary can be encouraging.
On the other hand, at any given time, circumstances beyond your control may cause you to lose your job. Therefore, it is always better to be prepared and have a backup plan, perhaps even multiple backup plans, to avoid being caught off guard.
While the reasons are obvious, it is striking that many end up falling into the trap of the comfort zone.
A monthly salary feels good after all, and no matter how real the fear of losing a job is, for various reasons, it ends up being relegated to the background.
Personally, at some point in time, I was becoming complacent and comfortable with the status quo.
Despite the precariousness of the job I had and the philosophy market, stress was crawling upon me, and I failed to channel it or translate it into something more useful.
Settling into one's status quo can have serious and detrimental consequences. In my case, it was an imaginary comfort. A contrived sense of safety that sooner or later I will manage to find something because I have the credentials as an entry ticket into the academic world.
During the pandemic, I was compelled to step out of my comfort zone. It was then that I realized, firsthand, the significance of honing a skillset beyond my field of expertise to navigate through real-world challenges.
Networking, marketing, copywriting, and design (even if it meant using simple tools like Canva) were all areas in which I lacked experience.
As Hassan pointed out in our conversation, drawing from the book The Start-up of You, it's crucial to adopt a startup mentality when it comes to our professional careers.
Bringing these ideas into practice is not easy. However, if this article or the podcast encouraged you to start creating a side hustle, feel free to reach out and let me know!
If you’re finding it difficult to choose a subject, Hassan suggests that your topic of choice fulfills the following 3 intersecting circles:
Interest: something you’re interested in, but not necessarily passionate about.
Experience: something you have direct experience in.
Market: something that has an active buy/sell market.
To conclude, I would like to share a quote that Hassan came across in the book The Start-up of You: "A million people overseas can do your job, what makes you so special?”
Tune in to the episode at the following links:
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You can find me on Twitter @decafquest.
Personal website.