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Do You Need A Side Hustle As An Executive ?

A few years ago I had an "aha" moment about my career.

It was during my first few weeks at Google, that I noticed something strange.

Many of the executives I was working with had a side hustle. Some were offering consulting services, others were board members, and some were building a product on the side.

At first, it struck me as odd.

Why would an executive with a full-time job need a side hustle?

But it didn’t take long to realize that they were actually creating leverage for their corporate careers while generating an additional income source.

And it wasn’t just executives at Google. I started noticing that the most in-demand executives in the startup world had a side hustle as well. It was part of what positioned them as industry leaders and helped them attract lucrative job opportunities.

These executives learned how to leverage their hard-earned title to their advantage, and used it to develop a portfolio career.

In today’s competitive landscape, with remote work options and with zero investment required to get started, launching a side hustle is a strategic tool to future-proof your career.

WTF Is a Portfolio Career?

If you are anything like me, you were raised to believe there was only one career option:

Find a steady corporate job. Entrepreneurship, freelancing, or doing all 3 wasn’t an option.

If you asked me 10 years ago, that would have been my answer. But something changed in the last decade, and we are now living in an era that provides a variety of new ways to design a successful career.

I didn’t have a name for it up until recently when I heard the term “Portfolio Career”.

This term draws an analogy from the Venture Capital world, where funds diversify their portfolios by investing in a large number of startups (bets), knowing that only some of them will pan out. It’s how they mitigate risks and maximize returns.

Similarly, in a portfolio career, instead of only making one big bet (your corporate job), you can diversify your income streams and professional pursuits to achieve greater resilience, flexibility, and fulfillment in your work life.

And if you do it well, your corporate career will fuel your side hustle, and vice versa.

Your Title is Worth More Than Your Salary

What comes to mind when you see people with these titles?

  • Top LinkedIn Voice

  • Forbes 30 under 30

  • VP of Marketing

You automatically assume: that these people know what they are doing.

We all rely on signals like titles to form opinions and shape how we perceive someone.

We use them as shortcuts to help us make decisions about who has authority, experience, and credibility.

And your executive title is no different. It’s a seal of approval that provides social proof and builds trust.

It gives you plenty of authority inside of your company, but it can also serve you outside of your organization.

For example, if you want to start a side business doing consulting, having that title can make customers feel confident buying from you.

Whether you are a Director, VP, or C-level exec, your experience can be monetized outside of work.

If you are not tapping into this potential, you are missing out on much more than additional income.

The Hidden Benefits of Starting an Executive Side Hustle

There is one obvious benefit to starting a side hustle: making more money. And more specifically, diversifying your income sources.

But you gain so much more when you choose to use your hard-earned title to your advantage:

1. Build a killer personal brand

Making a name for yourself in your industry as a sought-after consultant will upgrade your reputation.

It will help position you as the best in your field, and actually open doors to career opportunities.

Just look at Devin Reed. His consulting side hustle and the brand he built allowed him to move from one explosive startup to another, landing an extremely coveted opportunity in the tech world.

2. Grow your earning potential

Do you know how jobs have a salary band? Your goal is to be at the top of that band. It is so much easier to justify the top of the range when you have authority and respect. Just like one of my clients who recently stepped into a VP role at a startup. She casually mentioned how she consulted for YC-backed startups (the best accelerator in the world), and that experience positioned her at the top.

3. Learn How to Sell Yourself

Knowing how to sell and market yourself is key to building a successful business and landing executive roles. Starting a side hustle will push you to get comfortable with selling yourself and asking for what you want. You’ll learn how to negotiate and confidently push back, a skill you can use to secure a higher salary in your corporate career. I call that a massive win.

4. Great networking and relationship building

A side hustle requires customers. The easiest and fastest way to find them is to network with potential clients. You put yourself out there and start building relationships. If you ever find it difficult to network internally and build relationships with decision-makers, starting a side hustle might give you the confidence you need to network at work.

5. Build confidence

Something strange happens when you start a side hustle. It’s all on you.

While you can avoid doing something that scares you at your corporate job, there is nowhere to hide when you are the only one accountable. It forces you to get out of your comfort zone and stretch yourself. You take action you never thought you would, and the result is increased confidence. Confidence in your ability, your authority, and your worth. Confidence will show up in your executive role as well.

6. Create leverage in the market

You won’t stand out in a competitive market by being just like everyone else. There are tons of people who have an MBA, tons who worked for great companies, and many who have a track record of success. Having a successful side hustle can help you stand out from the crowd by providing proof that you are in demand. And as humans (hiring managers included) we want what’s hard to get… your side hustle can help you create FOMO. That’s how I managed to stand out in a sea of more experienced candidates (on paper) and landed a competitive VP role at a hyper-growth startup.

7. Future-proof your career

This is the bottom line. Whether you want to stay in corporate for the rest of your career or start a business in your 40s, a side hustle will give you options. It will keep you from being locked in with one employer, allow you to test out a potential business with minimum risk, and accelerate your personal and professional growth.

How To Get Started With an Executive Side Hustle?

This is probably the question that is going through your mind right now.

This side hustle thing sounds good, but how much work is it going to be? How do I even get started?

Let me answer some of these questions.

The best way to get started is to get started. You don’t need a website, a social following, a logo, or a company.

You need to decide who you want to serve, and what services you’ll provide. Write it down in a few words, and that’s your offer. And lastly, you need to open a Stripe account (or similar) to collect payments. It takes 5 minutes and costs nothing.

That’s it.

Now all you need to do is find your first customer.

You can tap into your existing network, ask for referrals, post about your services, or even do a cold outreach.

And once you learn how to get one customer, you rinse and repeat.


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