4 Ways Failure Led Me to Become a Solopreneur

“Had I ‘succeeded’ in my past endeavors, I’d probably be sitting in a corporate office racking my brain over some superfluous comment my boss made in our morning meeting.” 

-Sarah Lempa, Writer, Entrepreneur, and Creative Media Strategist

I used to crack jokes about being the black sheep of my business school in college. Mingling with corporate recruiters, relentless internship hunting, networking events that were more awkward than an eighth-grade dance—none of them were quite my forte. “What am I even doing here?” I’d ask friends with a sheepish grin, in between classes where I wrestled to keep my focus. Under the jokes, however, there was a gnawing fear that I wasn’t good enough.

Me and failure? Oh, yeah. We go way back.

We’re old pals, really. Between wiping tears on the sleeve of my Ann Taylor suit (that I loathed) after career fairs and feeling like I got punched after yet another job rejection, we’ve gotten to know each other painfully well. What I didn’t know back then was that failure had a secret agenda the entire time: To align me in a direction congruent with who I really am.

Two-and-a-half years, one self-designed career, and 40+ countries later, I couldn’t be more grateful for my so-called failures. Without them, I’d probably still be taking lunch break naps in my car at an office job. Here’s how each blunder and botch catapulted me into becoming a solopreneur.

1. Each rejection prodded me to try something new.

Early in college, I chased big-name corporate internships. I never received a single offer. Taking everything far too personally at age 19, I’d stew in the sullen sting of failure, agonizing over why I didn’t make the cut.

After moving on to pursue advertising agencies, I was beside myself that I had ever attempted working in corporate America. My personality wasn’t suited for a “normal” office, I thought. I should work somewhere with colorful bean bag chairs, a place where people swear in their emails, I convinced myself. While it was comparatively better, the agency world offered little improvement when it came to freedom. Not even all of the Friday office beers in the world could make up for that. As fate would have it, none of my job prospects materialized anyway.

With each perceived screw-up, I gained insights about what would actually make me happy. It wasn’t freedom within the office—it was freedom from the office. I wanted to travel the world like a crazy vagabond, not spend 97% of the year daydreaming of a meager 10-day vacation. That revelation was scarier than any rejection, as I knew it would be much harder to achieve.

2. I learned exactly what I didn’t want for my career—much faster.

A fancy name tag, gargantuan skyscraper office views, glossy high heels that echoed in hallways... I used to think I needed these things to be successful. It turns out that was only what other people around me wanted at the time. Failure bopped me on the head like a Whack-A-Mole, time and time again, saying you don’t want any of that anyway. I lusted after their approval, mirroring others’ dreams that weren’t suited for me. I can only imagine how much longer this realization would have taken had I not gotten turned down from the start. 

In a last-ditch effort to get a job that provided some semblance of freedom, I applied to be a flight attendant. I wanted to try freelancing while flying for a living, hoping I could figure out self-employment while on-the-go. I made it to the third round of the interview process and never got a callback. I sobbed at the news, thinking I had officially lost all chance at freedom in my career. Little did I know that crushing letdown would later lead me to take a leap into freelancing full-time, something I’d later look back on with immense gratitude.

“I wanted to travel the world like a crazy vagabond, not spend 97% of the year daydreaming of a meager 10-day vacation.”

-Sarah Lempa, Writer, Entrepreneur, and Creative Media Strategist

3. It made me a more resilient and courageous person.

Reminiscent of first heartbreak, those initial flops in your professional life can leave you feeling like you got dumped on Valentine’s Day. To make matters even worse, there probably isn’t any leftover chocolate laying around either. I used to put so much emotional stock into each application, meeting, and interview — forming lofty attachments that would only come back to bite me. As the years passed, I eventually learned to peel myself out of the pity zone a bit faster. 

Don’t get me wrong: Sometimes I still feel heart-sinking pangs of disappointment when things don’t go how I’d like. I’m only human, after all. The difference nowadays is that mishaps feel less apocalyptic; resilience has taken the stage. I started to accept (and even embrace) the unknown. Risk-taking became commonplace when I realized I wouldn’t get high rewards by staying comfortable. Failure is the devious cousin of risk, and you have to invite ‘em both unless you want your party to be painfully boring.

4. Without other options, failure forced me to try that one “crazy idea.”

Jobless as a fresh graduate, I couldn’t find a single reason to hold back. Without these bumps in the road, I would’ve never hopped on a one-way flight to Vietnam in pursuit of building my own location-independent career. I would have never felt the goosebump-raising thrill of building something that felt so authentically me in all ways. And I certainly wouldn’t have been able to manage the tumultuous roller coaster that comes with paving your own way as a solopreneur. 

Had I “succeeded” in my past endeavors, I’d probably be sitting in a corporate office racking my brain over some superfluous comment my boss made in our morning meeting. 

Like a friend dishing out tough love after a breakup, failure yanked my hand and swung me exactly where I needed to be. And while we’ve come a long way, this is a lifelong journey.

Photo: Courtesy of Sarah Lempa

About the Author: Sarah Lempa is a writer, entrepreneur, and creative media strategist covering the joys (and challenges) of freelancing, travel, and solopreneurship. Her work has appeared in Business Insider, Fodor’s, and SUITCASE Magazine, among others. Currently based in Indonesia, she’s called multiple countries home and has ventured across 6 continents along the way. When she’s not chipping away at a piece, you’ll find her jamming out to groovy beats or riding a motorcycle. Keep up with her on Instagram @travelempa.

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Know Your Worth, Then Add Tax: The Multi-Hyphenate's Stress-Free Guide to Doing Your Taxes

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.

5 Solutions to Common Solopreneur Struggles

Photo: Godisable Jacob from Pexels

If you’re self-employed, you know how rewarding it can be to work for yourself: You get to do the work you love, take on clients you enjoy working with, and set your own schedule. But, of course, there are also challenges to solopreneurship. We reached out to our Create & Cultivate Facebook community to find out some of our members’ biggest difficulties in working for themselves. Read on to discover a few solutions to the challenges of running a one-woman show.

1. I MISS HAVING COWORKERS

Striking out on your own can be a scary process, especially without the support of HR, accounting, and marketing departments to back you up. “The weight of every decision seems 10x because I don’t have anyone to talk through the pros and cons with,” says Farah D., who owns a vegan bakery. “Trying to be good at everything all at once is a big struggle.”

Thanks to the internet, it’s easier than ever to be a solopreneur who works alone but doesn’t have to feel alone. Facebook groups and online communities (like our Create & Cultivate group!) offer a free place to bounce ideas around, ask for advice, and even build personal and professional relationships with other talented entrepreneurs. You can also consider working a day or two a week from a coworking space (many allow drop-ins and offer off-hours memberships at discounted rates).

But it’s not just a matter of existing in these spaces—you have to be an active member who’s open to meeting new people and starting conversations, even when it’s uncomfortable. By putting yourself out there both IRL and on social, you’ll likely meet like-minded freelancers and solopreneurs who can be a valuable asset to your business.

2. I DON’T KNOW HOW TO PLAN FOR TAXES

Jucel M., a designer and illustrator, says her biggest self-employment struggle is budgeting for freelancer taxes. “I can invoice and keep track of my transactions, but [I need help] on how to translate that into filing my taxes.”

No doubt, taxes are a surprisingly large part of freelance life—especially those pesky quarterly payments. But there are simple online programs like TurboTax that can help. They help you file with confidence with one-on-one expert help and they also do a wide search for industry-specific deductions that others might miss. They also offer several online tools to help manage your taxes throughout the year such as their tax bracket calculator, self-employed expense estimator, and handy documents checklist so you are prepared come tax time.

3. I CAN’T STOP WORKING

Entrepreneurs are known to hustle. But how do you know when it’s time to call it a night? “My biggest struggle is turning myself off from ‘work mode,’” says Sierra M., a digital strategist. “If I’m just hanging out, I figure I can work on some aspect of my business—why not? So I don’t really let myself relax.”

Sound familiar? It can be hard to turn your “work brain” off and chill out when you’re the only one keeping your business running. But in the name of wellness, it’s important to truly shut down every once in a while. We’re not saying you have to enact a rigid 9-to-5 schedule (although that works for some people!), but you can start with “I’m not going to open my laptop on Saturdays” and go from there. Remember that because you are your own boss, nobody is looking out for your health but yourself—take care of your body and mind! And if that doesn’t convince you, know that studies show work-life balance increases productivity and creativity, so you’re really doing yourself a favor by powering down for a bit.

4. I’M NOT SURE IF IT’S TIME TO OUTSOURCE WORK

Deciding when to bring on help can be one of the most stressful parts of running a business. “Growing beyond being a solopreneur is a big topic of conversation within my community,” says Kristen P., brand stylist & creative director. “When is the right time? What is the right first hire? Etc.”

Hire too early, and you’re likely wasting money on a salary for someone you don’t need. But hire too late, and you face a mountain of work you can’t accomplish to your own standards. So when is the golden window of time for hiring? Experts say you should only hire someone when you’re regularly turning down work, you’ve found a new revenue stream (and an addition to your team would make you money), or you don’t have time to focus on important business aspects like customer service or accounting.

If you’re not ready for full-time employees, try hiring a contractor for a single project and see how it goes. You’ll learn how to manage and delegate, your project will move forward, and you’ll get a glimpse into what it’ll be like to make your first hire.

5. I DON’T KNOW HOW TO SHOW MY VALUE

You’ve built a business from the ground up. You’ve tackled finances. Your clients are happy. But how do you create an effective marketing strategy to keep revenue coming in? “My primary struggle is coming up with the best ways to show potential clients the value of what I provide,” says Brandi H., creative director.

To create a marketing plan, write down what you specialize in and who your dream clients might be. This will help hone your marketing strategy to bring in the type of business you’re vying for. Next, get started on the actual content—perhaps this is a blog, an elevator pitch, or a killer portfolio site. Your content will depend on your line of work.

Lastly, find the right space to share your work far and wide. This may be through writing for a publication, sharing your portfolio on career sites or in Facebook groups, being a guest on a podcast, speaking at an event, sending cold emails, or investing in a booth at a conference. Do your due diligence to find out which would be most profitable for your business and go forth confidently like the savvy solopreneur you are.

This post was originally published on January, 8, 2019, and has since been updated.

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Solopreneur Tax Tips: The C Corp Entrepreneur

Filing taxes when you’re an employee is hard enough. But what happens when you strike out on your own? There’s a big difference between business structures—whether you’re operating as a sole proprietorship, LLC, or S corp, there are different planning and filing processes for each. Today, we’re diving into how to handle taxes when you’ve chosen one of the lesser-known structures: a C corporation.

Above, entrepreneur Natalie Elizabeth Ellis, founder of BossBabe—sits down with Lisa Greene-Lewis, TurboTax CPA, to learn how TurboTax Self-Employed can help her stay on top of her C-corp tax obligations throughout the year. Read on to learn a little more about Natalie and see how TurboTax can help you prepare and file taxes confidently. Plus, we're gifting 30 readers with a FREE TurboTax Live Self-Employed product code (valued at $169.99) below—so you can file for free this season!

Tell us a little about your company, BossBabe.

BossBabe is one of the largest and fastest growing online communities of ambitious women in the world. Our mission is to connect, inspire and teach ambitious women how to create their own versions of success. We aim to help 1 million women create $1billion in revenue.

What’s been your biggest challenge in getting BossBabe off the ground? What’s been your proudest moment?

I feel like my proudest moments come in waves every day - whether that's seeing that we've been able to help a woman generate over $500,000, or quit their full-time job to work on their business, or even crack 10K followers on Instagram. I see all those wins as big wins and the real "why" behind what we do. It's also been incredible to be featured in Forbes, Entrepreneur and Business Insider alongside other incredible entrepreneurs who are driven by big missions.

I'd say my biggest challenge with BossBabe was being able to respond to how quickly we scaled. From finding team, to setting up the right systems, it was such a struggle to do it as quickly as we needed to.

Our C&C readers agree—scaling up can be scary! Thankfully for Natalie and the rest of our community, TurboTax Self-Employed comes with a free year of of QuickBooks, so you can spend less time on the logistics of tracking expenses and more time focusing on the growth of your booming business.

What advice would you give to would-be side hustlers who don’t know where to start in getting their business off the ground?

Stop thinking, start doing. Make sure that you're setting aside time every single day to DO something and are actively moving the needle towards where you want to go. Too often we can be paralyzed by decisions, fear and unknown. I believe that clarity often comes from doing and learning, so I always push my clients to DO very quickly.

What are you most excited about for your business in 2019?

In 2019, I'm so excited for all of the new products we're launching. We'll soon have a podcast and we're also creating a product to help other entrepreneurs grow their community online in the way we did (we have over 1M women in our community!). I'm also just really excited to continue supporting the women inside our membership and mastermind products grow their own businesses so that they can inspire and support people in THEIR audiences. We really value the idea of being multiplyers.

Want more tips for tax time? Check out our guides for side hustlers and freelancers! or Or you can dive into TurboTax Self-Employed here—and enter to win a free TurboTax Live Self-Employed code below!

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!

30 readers will receive a FREE TurboTax Live Self-Employed product code (valued at $169.99). Simply fill out the form below to enter to win. The winner will be chosen randomly and contacted via email. Good luck!

This post is sponsored by TurboTax.

Solopreneur Tax Tips: The Freelancer

Making your own schedule, choosing your clients, and sweet, sweet freedom—these are just a few of the many perks of freelancing. But with that freedom comes great responsibility…including being on the hook for filing self-employment taxes. Above, content creator Grasie Mercedes—who splits her time between acting, writing, directing, and blogging—sits down with Lisa Greene-Lewis, TurboTax CPA, to learn how TurboTax Self-Employed can help freelancers stay on top of their tax obligations throughout the year. Read on to learn a little more about Grasie and see how TurboTax can help you find deductions, file confidently, and keep more of your hard-earned money in your pocket. Plus, we're gifting 30 readers with a FREE TurboTax Live Self-Employed product code (valued at $169.99) below—so you can file for free this season!

To quote your Instagram bio, you “do a lot.” You’re an actor, writer, director, and blogger—what do you like most about working on so many different projects?

I love to keep busy and I love everything entertainment, so for me, it just makes sense. Now, more than ever, actors "do it all": they direct episodes of the shows they're on, they create their own series, and they continue to act in everything from commercials to TV to major motion pictures. I think it's wonderful and exciting! Blogging is something I started over eight years ago as a creative outlet to supplement my then-styling career, which was supplementing my acting endeavors. From there, I turned it into a brand/business that I can have forever (or as long as I want)! Having so many things to work on and work toward is so special to me...I never get bored "working" and that's a dream. I'm so grateful to be able to do what I love, every single day. 

What’s your biggest challenge in having so many different business ventures on your plate? The biggest reward?

The biggest challenge is when the various ventures start to interfere with one another. Acting is a crazy business with an unpredictable schedule so there have been plenty of times where I have to miss an event, trip or opportunity because I have to be in town for pilot season or for a callback, etc. When that happens, I just have to weigh my options and then deal with serious FOMO when I see what I missed on social media. The biggest reward is hitting new goals in any given venture. I just signed with an amazing talent agent for writing, I'm developing my first pilot with a great production company, and my first film is still getting accepted into major film festivals! Those are all huge wins for my writing and directing careers, which I started less than two years ago! 

We polled our C&C community and found that many freelancers share the same concerns as Grasie—conflicting schedules and deadlines can make solopreneurship difficult. Luckily TurboTax Self-Employed makes it easy for freelancers to track and file quarterly estimated payments, so you can focus your efforts on your work and your clients.

What advice would you give to someone who wants to go freelance but is worried about how they’ll make a stable living?

This is a tough question. I think you have to weigh your options and responsibilities. When I decided to quit my day job and move to LA to be an actress/creative, I was in my late 20s with zero obligations. It was easy to just go for it because it was just me. No kids, no mortgage...not even a pet! If you have that freedom, then just GO FOR IT full throttle! Do whatever it takes to pay the bills (legal things only, of course). Wait tables, get a temp job, be a barista...all the while, make sure you are working on your creative endeavor daily. If you're responsible for more than just yourself, I would say keep your day job as long as possible, save money where you can and again work on your creative endeavor daily until it's bringing you enough money to quit your day job. The only difference between these paths are that the first one usually gives you more time and freedom to pursue your dream. But regardless of which path you take, the most important thing is to WORK HARD and WORK EVERY DAY on whatever it is that you want to be doing! Dreams are wonderful, but they only come true if you work your ass off. 

What are you most excited about for your business in 2019?

Excited to revamp my blog and to work as a writer and director more! Acting will always be "my first born" and something I'll never stop doing, but creating my own work (TV shows/films) is my number one priority at the moment. 

Want more tips for tax time? Check out our guides for side hustlers and C corp entrepreneurs! or Or you can dive into TurboTax Self-Employed here—and enter to win a free TurboTax Live Self-Employed code below!

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!

30 readers will receive a FREE TurboTax Live Self-Employed product code (valued at $169.99). Simply fill out the form below to enter to win. The winner will be chosen randomly and contacted via email. Good luck!

Not quite a full-time freelancer?

If you’ve got a side hustle and need help with filing taxes, be sure to check out last week’s guide. Stay tuned for next week’s post for more solopreneur tax tips—and enter to win a free TurboTax Live Self-Employed code below!

This post is sponsored by TurboTax.

Solopreneur Tax Tips: The Side Hustler

The side hustle economy is real—37 percent of the workforce has a side hustle (and more than half of the Create & Cultivate staff has one!).

Having a side gig is exciting—you’re about to make more money, after all! But what you might not be prepared for is tax time. Above, our very own C&C employee Tyeal Howell—who moonlights as a podcast host at Bosshood—sits down with Lisa Greene-Lewis, TurboTax CPA, to learn how TurboTax Self-Employed can help side hustlers run their business more efficiently in preparation for April 15. Read on to learn a little more about Tyeal and see how you, too, can use TurboTax to file with confidence. Plus, we're gifting 30 readers with a FREE TurboTax Live Self-Employed product code (valued at $169.99) below—so you can file for free this season!

Tell us a little about your podcast, Bosshood. What inspired you to start the pod?

My best friend Ryan and I launched our podcast Bosshood to give young professionals and aspiring entrepreneurs access to people, resources, and information on accomplishing their career goals and working their way into the positions they aspire to be in. When we were graduating from college back in Ohio, we didn’t have the connections or resources we really needed to launch our careers in New York City and Los Angeles, so we created them ourselves and finessed the glow up. Bosshood is a fresh spin on adulting for millennials who obsess over professional development books, love coffee, and hangout at rooftop parties in cool cities.

What’s your biggest challenge in having a side hustle? The biggest reward?

The biggest challenge is definitely time management. After spending Monday through Friday 9-6 looking at my phone and my computer while sitting at my desk for my day job, the very last thing I want to do is more work. The biggest reward comes after that extra work is done for Bosshood and people text and DM us about how inspiring and encouraging it was for them to hear our stories. It’s even cooler when we travel and people come up to us like, “I loved your podcast interview with Johnathan Jackson on Bosshood! I was inspired and encouraged."

Tyeal’s not alone—we’ve heard from our C&C community that time management is a common problem for many side hustlers. The great thing about TurboTax Self-Employed is that it uncovers industry-specific deductions personalized to your line of work, so come tax time you won’t be racking your brain to think them up yourself. Your purchase also comes with a free year of of QuickBooks, which makes expense tracking effortless—so you have more time to focus on actually building and growing your business.

What advice would you give to would-be side hustlers who don’t know where to start in getting their business off the ground while working at a 9-to-5?

I’d say dedicate one of your weekend days where you’re completely free of work obligations to just brainstorm. Sit at a cafe, write out all of your ideas, and just envision what you want those side hustle dreams to manifest into. Then find someone to hold you accountable for the next steps. Start by starting! And read WorkParty the book!

What are you most excited about for your business in 2019?

I’m most excited to continue learning new things, failing at things, adjusting my strategies, and producing the content. Season 2 of Bosshood will be coming soon and you can subscribe now on iTunes or listen on Soundcloud! Boss up!

Want more tips for tax time? Check out our guides for full-time freelancers and C corp entrepreneurs! or Or you can dive into TurboTax Self-Employed here—and enter to win a free TurboTax Live Self-Employed code below!

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!

30 readers will receive a FREE TurboTax Live Self-Employed product code (valued at $169.99). Simply fill out the form below to enter to win. The winner will be chosen randomly and contacted via email. Good luck!

This post is sponsored by TurboTax.