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16 Questions To Ask Yourself Before You Pursue A Side Hustle

Forbes Coaches Council
POST WRITTEN BY
Expert Panel, Forbes Coaches Council

In the growing gig economy, many professionals are taking on a “side hustle” in addition to their full-time job. More and more Americans are choosing to pursue freelance work, sell handmade products, drive for rideshare services and more to earn supplemental income and achieve their goals.

While the idea of extra money is appealing, side hustles are not for everyone. That’s why we asked 16 Forbes Coaches Council members what they think everyone should consider when deciding whether or not to take on a side hustle. Here’s what they believe you should ask yourself before pursuing a new venture.

Photos courtesy of the individual members.

1. Will it build your career and skills?

There are many reasons for side hustles, and extra cash is one. Knowing why you are doing more on the side will be the key to long-term success. Need extra cash for the holiday season? Go ahead and take a short-term job, maybe in retail or some other seasonal opportunity. If your side hustle will be a longer-term proposition, make sure the work you do will also build your career and skills. - Cindy Stack, Whole-Life Leader

2. How will your employer feel?

I see people sharing and oversharing about their side hustle on LinkedIn, Facebook, Pinterest and Instagram. In some cases, the main employer is taking notes and is not happy. When I talked to one friend who was celebrating a milestone publicly, he said, "My employer can't stop me. It's my time." Employers often care and are watching. You should pay attention to how much you can or should share. - John M. O'Connor, Career Pro Inc.

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3. Can you deliver a great customer experience?

Profitable side hustles are as much about the people as the problem you're solving for them. When considering whether it's right for you, make sure you not only have the capacity for the project work and contract administration, but also the bandwidth to deliver a great client-customer experience. Because if you do, projects will likely multiply and your side hustle may just turn into a main gig. - Tracy King, InspirEd

4. Will your intellectual property be safe?

Side gigs such as Uber or TaskRabbit likely won't impact your day job. However, if you are in a field like technology, products or services, be careful about protecting your intellectual property. Secretly working on your side gig during the day may put your IP at risk. Conducting business on your employer's time may give them rights to your IP and revenues. - Karan Rhodes, Shockingly Different Leadership

5. Do you have a purpose besides earning money?

Though the standard considerations such as viability, earning potential and other similar factors should be the main basis of the decision, a secondary factor is often overlooked: dual purpose. A side hustle can and should have more than just a single goal of earning money. It should also help determine if it is the right business to eventually grow or do full time. - Kamyar Shah, World Consulting Group

6. Do you have the time and energy?

Taking on a side hustle can be time-consuming and, in the beginning, not have a lot of dividends. Decide whether it is worth it. Do you enjoy the work that you do? Is there a market for it? Do you have the right sales tactics to make it work? Can you identify the right people to sell it to? Ask yourself these questions before you get started. If you answer yes to all of these, then do it! - Monica Thakrar, MTI

7. Will it create a conflict of interest?

The single most important question to answer about a side hustle is: "Does this form a conflict of interest with my primary work?" I encourage my employees to take on side business strategies, but some have to be coached to not use their primary position to develop opportunities. Side hustles should be completely independent of your primary role with different people, clients and resources. - Tom Kolditz, Doerr Institute for New Leaders

8. Can you set realistic goals for your side hustle?

Setting goals for your side hustle gig allows you to keep things in perspective. Your goals should be based on the amount of time, energy, effort and money you are willing to dedicate to your side hustle. Knowing whether or not you want your side hustle to supplement your primary work or replace your primary work will help you set realistic goals for what you want to achieve and in what timeframe. - Lori A. Manns, Quality Media Consultant Group LLC

9. Does it light you up?

A side hustle can bring you many benefits, including increased cash flow. It's going to draw on your time, energy and resources. Make sure it's something that lights you up to keep you going on those days when all you have going on feels like just too much. Many days, the money makes it worth it, but to sustain the momentum, you're going to have to really want to do what you're doing. - Michelle Barr, Michelle Barr

10. Will the income outweigh the costs?

Before you jump into a side hustle, add up all of the direct and indirect expenses and costs involved. For example, want to drive for a rideshare company? First, add up the average monthly cost of gas, insurance, maintenance (including tires), time spent cleaning the car and sitting in an airport cell lot waiting for a rider. It could turn out that your hourly rate is far less than you thought. - Gregg Ward, The Gregg Ward Group

11. Do you attribute a feeling of joy to your hustle?

We make decisions based on our dominant feeling because it is our feelings that validate our decisions. If we hustle simply because we want to make more money, we are indicating a lack of feeling, which will trigger similar beliefs/memories/decisions into our lives. But if we attribute a feeling of joy with our hustling, then we feelingly welcome more money and enjoy it. We are what we attract. - Anne Beaulieu, Walking Inside Resources Inc.

12. Will it help you achieve your primary goals?

It's great to have a side hustle if it serves to achieve your primary non-side hustle goals. If not carefully analyzed, your side hustle can take too much time, energy and resources, taking you away from achieving maximum success in minimum time for your primary goals. Research, analyze and plan your side hustle before launching. - Linda Zander, Super Sized Success

13. Are you truly entrepreneurial?

Everyone wants the dream of financial freedom, but through two decades of career transition assistance, I've seen many people who simply aren't wired to get their values met through self-motivated employment. If you "shine" with employer feedback, need deadlines to complete tasks or struggle with time management, any of these may spell dissatisfaction. Consider a career or personality test first. - Laura DeCarlo, Career Directors International

14. Do you have a solid business plan?

A "side hustle" is really just a small business, which succeeds with a business plan. Build a business plan to define your vision, goals, expectations, budget and the effort it will take to meet the goals you are projecting. Define who is successful and why clients and customers love them. Investigate, but do not imitate. If you are motivated and it makes financial sense, give it a go. If not, don't. - Bobbie Goheen, Synthesis Management Group

15. Does it align with both your natural abilities and your passions?

Create a list of passions, hobbies and activities you enjoy doing in your free time. Compare that list with your natural abilities to hone in on the best fit. As the new side hustle will eat up spare time on the calendar, make sure to choose something you truly love and enjoy doing. To maximize success, consider obtaining a vocational certification or taking a masterclass in the field. - Lourdes Mestre, Marketing Muses

16. Is this really what you want?

Is it really extra cash or is this side venture what you're truly passionate about? If it's the latter, there's more to consider like time, energy, resources and support. Side hustles are great for extra cash, but can be a huge consumer of time and focus. Don't lose sight of what you ultimately want. Set clear expectations for each role you play and leave room for you! - Miranda VonFricken, Miranda VonFricken Mastermind Coaching

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