As you may know, I live in NYC. Last Thursday, our #stayathome mandate was extended an additional month. Honestly, I wouldn’t be surprised if it gets prolonged beyond that. 

Along with this latest update from Governor Cuomo, I got word that two speaking gigs that were postponed in March to the Summer have now been moved to 2021 – presuming we return back to “normal” and can meet in large gatherings. And I have it on good authority that a major tech firm has suspended all events and non-essential travel for its employees until 2021.

Folks, I don’t mean to sound like Debbie-downer when I say what I’m about to say, but… 

Even when our “activities” return to some semblance of what we may consider normal, it is going to take quite a while for our economy, our governments (city, state, and federal), our social and education institutions, and our businesses – especially small businesses – to recover.

And while that may sound incredibly dismal, times of recovery can be fruitful and an ideal period to get your side-hustle on — either to start one or to bolster the one you already have. 

Do What Mommy Said

You’ve likely heard the maxim: “Don’t put all your eggs in one basket.” 

When it comes to investing, diversification, or having a portfolio of holdings that move in the opposite direction, is a version of this maxim. 

Similarly, when it comes to running a business, diversification looks like offering varied products and services to different audiences. 

Having a side-hustle does the same thing, because it gives you another income stream. With this additional income stream comes a little bit more income security, and overall financial stability and security that is more in your control

Perhaps you’ve never dreamed of being an entrepreneur. But the truth is we’ve been moving in this direction of what I call  the “accidental entrepreneur” for a while. 

Heck, when I wrote my book, “Financial Intimacy,” which was published in 2009, I remember sharing a stat from the Bureau of Labor Statistics about how employees were on track to changing jobs every 4.2 years. Drastically different from the careers of folks of my mother’s generation or even at the start of mine. The BLS stat really highlighted the evolution of the employer/ employee relationship, which coincides with the shift from defined-benefit plans to defined-contribution plans. But I digress…

My point is this: COVID-19 has amplified the dynamics of the relationship between working and financial stability and security that were afoot before the pandemic and health crisis of 2020

Thus, more and more people are needing to supplement their income either because a layoff took their household from two-incomes to one-income or from one to none; their hours were slashed; or an increase in their expenses necessitates more money coming in.

And what is true when it comes to investing or running a business is also true for a side-hustle: It’s not simply about having “more;” it’s about strategically having more. HUGE difference!!

Is Now Your Time?

In a different context, I might talk about side-hustles more in the vein of expressing your creativity that earns you extra money to meet specific expenses or fund specific goals.

Today, though, I want to talk about it as a key part of your professional and financial strategy – whether you currently work full-time; were downsized, but plan to return to FTE as soon as you possibly can; or already have a side-hustle, but don’t really treat it like a business. 


Because COVID-19 has made it crystal clear that having multiple streams of income is no longer optional. It is imperative!

Maybe you remain in shock and you’re not quite ready to even consider starting a side-hustle. If true, bookmark this for when you are. 

But if you’re ready to start or bolster your side-hustle and make it a (more) lucrative and profitable endeavor, here are a few suggestions:  

Do a skills inventory

Even if you already have a side-hustle, taking a step back to evaluate the skills you bring to the table can be really useful. This is especially important because often the skill you tend to “take for granted,” because of how easy it is for you, is the one that others value tremendously, e.g., advising, conflict resolution, strategic thinking, project management, designing, deep listening, communicating, data analysis, to name a few.

And if you’re still stuck, think about the question/s your friends ask you for help with the most.

Don’t skip this suggestion, because it’s part of what factors into your pricing strategy and approach. Further to this point, price as if it were your full-time business.

Monetize a hobby

Some people cannot fathom turning their hobby into a money-making endeavor. And those that do charge sometimes short-change themselves because it’s a hobby. If this is you, now is the time to reconsider your mindset about getting compensated and by how much for a pursuit usually reserved for your leisure time. 

Don’t focus on the pretty 

Here’s what I mean: Yes, a well-designed website and graphics for social media help. But not as much as getting clients! So be wary of prioritizing the bells-n-whistles over the activities that lead to new business.

Use your time strategically

You don’t necessarily need to allot a large amount of time for your side-hustle, but it does need to be focused and planned ahead of time. 

You’ve likely heard the suggestion that constraints give rise to creativity, yes? Well, times of disruption, the likes of what we are collectively experiencing right now serve, as the “constraints” – including that of time – that can often spark your creativity.  

The “Accidental Entrepreneur”

I don’t know if you’re reading this as one of the 22 million people recently unemployed. I don’t know if you’ve had to close a business. Truth is I write this not knowing any details, for the majority of folks reading this, of how precisely you’ve been impacted by COVID-19 – in terms of your work or your finances.

But what I do know is that if your work and finances have been affected, you’ll need to regroup. You’ll need to regroup if you own a business; you’ll need to do so if you don’t. And if you fall into the latter camp, starting or bolstering a side-hustle is one way to regroup when you’re ready. And, I hope the above can aid you in that endeavor of making sure it is strategic.

Plus, as I said earlier, if you work (or did until recently) in a more traditional full-time employment position, I do believe having a side-hustle will become the “new normal.”

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