With the current COVID-19 situation, we know these are difficult times for both self-employed individuals and small businesses. In an effort to support and empower our self-employed community, we’re sharing step-by-step guidance on how to easily and affordably file your self-employed taxes with TurboTax.

The rise of the gig economy has given us multi-hyphenates, a.k.a. people who’ve built successful careers out of juggling more than one job at a time. In fact, more than eight million people—about 5% of the workforce—have more than one job. And, fun fact, the average self-made millionaire has at least three streams of income—65% have three streams of income, 45% have four, and 29% have five or more.

Of course, being a solopreneur with multiple side hustles is exciting—after all, you’ve mastered the art of multiple streams of income!—but that means tax time can be a bit complex (hello, 1099s galore). 

In anticipation of the new extended tax deadline, July 15th (a.k.a. this year’s Tax Day), we sat down with Lindsay Luv, a multi-hyphenate DJ, influencer, sommelier, and more, to find out how TurboTax Self-Employed can help multi-hyphenate solopreneurs file their taxes with confidence. With the changing COVID-19 situation, these are unprecedented times. Find out all the new tax changes and understand what the Coronavirus relief bill means for self-employed taxpayers by visiting the TurboTax blog.

Be sure to keep reading until the end for the chance to win a FREE TurboTax Live Self-Employed product code (valued at $250, includes ad-on services).

Join the solopreneur tax conversation by using the hashtag #solopreneurtaxtips. Don’t be shy! We all have questions about taxes (especially now), share yours on social too!

CREATE & CULTIVATE: As a DJ, music supervisor, influencer, and sommelier, you're a modern multi-hyphenate with many careers intersecting at the same time. What advice do you have for those reading this who don't have their eyes on one career path and feel split into different areas? How do they go about it? 

LINDSAY LUV: I believe expanding your brand should feel natural. If you find yourself drawn to another potential career path, perhaps think about what you’re already doing and how it can lend itself to the other. I never say I am “switching gears” because that sounds like you are closing the door on what you have already done; rather I say I am “expanding my brand” because that simply opens more doors. You never lose the skills you have already built, so why not develop and share more as you go! 

Also, the difference between those who say they are going to do something and those who actually take the plunge is vast. Sometimes you need to just rip the bandaid off! When it came to getting certified as a sommelier, I simply signed up and paid for the class and then showed up: that's half the battle! Wine goes hand in hand with music and events and sharing my finds (i.e., influence) so I am always thinking of ways to overlap my skill set. There are talkers and doers, and people respect action the most.

With your many careers, it’s safe to say that you’ve mastered the art of multiple revenue streams—and we here at Create & Cultivate love a woman who isn’t afraid to shy away from wanting to build a profitable business—So, can you tell us, why is it important to diversify?

With humans living longer lives they are actually predicting many of us will indeed have multiple professions across a lifetime! Just like relationships change and grow over time so do our interests and skill sets, and it is important to check in with yourself each step of the way and reflect on how your profession is serving you and how you are serving it. 

I am someone who always loves to be steps ahead. If I see a door starting to close (whether by choice or otherwise), I am thinking of which ones I can open: which parts of my career, relationships and learnings can I utilize for a new profitable task.

Working for yourself means you have to hustle and keep up with both your own goals and the demands of the market. Since I started working for myself, so many elements keep changing from social media to client’s needs and unless you are evolving with them you are lagging behind (and losing money in doing so.)

As we’re sure you can attest, you have to fall in love with the numbers when you’re running your own business, especially when that involves managing multiple income sources—What are some of the hardest money lessons you've learned along the way? And what are some of the tools you use to stay on top of your business financials?

As my own agent, sometimes it is awkward to chase down payments due. You run that line between wanting to seem relaxed with clients, but also simply needing to be paid for work done. Sadly, sometimes clients will put you in an awkward spot with pay delays or trying to pull out of things last minute, etc. I find it is helpful to have an assistant oversee the communication about payment with clients so you don’t always have to be the face of the tedious back and forth that can occur. 

I also leverage technology to remind myself of when payments are due and space out reminders to follow up. I use resources and tools such as QuickBooks Self-Employed to keep myself organized year-round, keeping track of my personal and business expenses as well as receipts. I can import all my business expenses to TurboTax Self-Employed making taxes a breeze! I like their Live product since it brings the best of both worlds, the ease of technology plus the human touch and expertise of a real tax expert. At the end of the day, you want to make sure you feel confident you are getting your self-employed taxes done right and are getting every dollar you deserve. 

You've been very smart and savvy with your business and it's been incredibly profitable—Where do you think is the most important area for a solopreneur or small business owner to focus their financial energy? Why? 

The reality is you should focus your heaviest energies on hustling and maintaining work wherever you are gaining the most momentum. For me, that has always been DJing, but now, with my social media growth, I am seeing new profitable opportunities arise in a variety of areas outside of the decks, so it has my wheels spinning on how to grow those. Keep pushing where the money already is, but reach out for everywhere it could be!

Do you think you have achieved financial freedom? If not, what is preventing you as a self-employed professional to get there? What would you need to get there?

Yes! I have been self-employed and my own agent for over ten years, which feels like freedom to me. I am able to comfortably afford a lifestyle I feel good about and contribute to my family, which is the best you can hope for. I also balance between being a full-time mom and a working mom by accepting quality over quantity job opportunities. 

With that being said, human nature is to want more, so in some ways, working for yourself is always complicated and you never can fully relax into a full feeling of freedom. It is important to never get too comfortable because being self-employed always means the onus is on you to hustle and grow. While a lot of work does come to me after having established myself over a decade, it is important for me to touch base with all my clients regularly and share my successes; plus, remind them of all we have done and what we can do going forward!

What are you most excited about for your business in 2020?

I have been putting feelers out for so many possible brand expansions and seeing which ones stick. I am never afraid to reach out to great contacts or throw out ideas and see which ones materialize, as I believe both my business acumen and skillset can lend themselves to a variety of areas, from public speaking, hosting, podcasts, music supervision, influencer collaborations, consulting, sommelier opportunities, and more. Not every one of these will become the next big (or most profitable)  part of my brand, but without opening up to a multitude of ideas and putting some muscle behind them you won’t know which one could and will! 

Our friends at TurboTax were nice enough to share a giveaway with Create & Cultivate readers so you can file your taxes for FREE this season—all from the comfort of your own home!

30 readers will receive a FREE TurboTax Live Self-Employed product code (valued at $250, includes ad-on services). Simply fill out the form below to enter to win. The winners will be chosen randomly and contacted via email. Good luck!

TurboTax Live combines the ease and technology customers know and love about TurboTax with on-demand credentialed CPAs, Enrolled Agents, or Tax Attorneys, for ultimate convenience and confidence. You can connect live to a team of real credentialed tax experts in English or Spanish, for unlimited tax advice and a final review before you file.

Giveaway now closed, thank you for entering! We will email the winners directly.