Episode 11: The Truth About Freelancing

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In this episode, Hilary unpacks the state of freelancing in the U.S., the drawbacks of freelancing, the benefits, and how to know if freelancing is right for you. 

Episode Highlights: 

  • Freelancing is massive. 53 million Americans are freelancers (That’s about 1 in 3.)
  • Freelancing is growing. By 2020, 50% of the U.S. workforce will be freelancers.
  • Expectations are shifting. 32 % of Millenials believe they will be working “mainly flexible hours” in the future. 
  • Technology makes it possible. 80% of millennials use social media as a means of finding work. 
  • 84% of freelancers find purpose working the gig economy.
  • 97% of freelancers say they are much happier than permanent workers. 

10 characteristics of people who thrive as freelancers:

1. You value autonomy. You are energized by making your own schedule. The idea of being your own boss feels right to you. When people say "I want to work in-house because I want to be a part of a team" it's kind of difficult for you to understand. 

2. You like non-traditional hours. You don't hold a grudge if you need to work early in the morning or late at night. You actually prefer not to track hours but rather to just work until the work gets done.

3. You're highly organized. You are highly skilled at keeping track of deadlines and workflow. Project management may not be your favorite thing, but you can do it. You're great at keeping up with details whether or not you feel like that's your highest and best use. 

4. You're cool with alone time. If you're a head down "work hard/play hard" kind of person, working at home may make sense for you. 

5. You don't need outer accountability. You can stay on task and check off your to do list even without a boss checking in on you. You are intrinsically motivated. 

6. You thrive on variety. You like the idea of multiple projects for multiple clients. 

7. You’re not intimidated by invoicing or negotiating contracts. The numbers side of getting paid doesn’t stress you out. In fact, it motivates you and inspires you to set goals. 

8. You actually feel like freelancing is beating the system a little bit. Some people think freelancers have the short end of the stick but any time you’re able to take a Friday off, bum around in yoga pants all day or work poolside, or strategically work faster to take on more clients and make more money, you know that you’re the real winner here. 

9. You're fine with sacrificing earning potential or benefits. It's worth it to you to sacrifice promotions or typical benefits like a company matching 401K in order to have the benefits of working at home. 

10. You're very good at connecting with people. Whether you’re building relationships IRL or via referral or social media, you can build rapport quickly with people who you don’t see face to face all the time

Do you dream about launching a freelance career? Freelancing is an amazing way to strike out on your own and work on your own terms or build a supplementary income stream.

Join Hilary for Going Freelance: How to Launch, Market, & Build Your Freelance Career at the Lemon Collective on August 23 at 7 PM. 2-hour intensive workshop you will get a crash course on all things freelancing as Hilary Sutton shares what she has learned over eight years of building a freelance career. You'll walk away with tons of practical information on everything from what you need to do know to launch a freelance business to creating a smoothly operating freelancing machine.

Connect with Hilary on TwitterInstagram, and Facebook.

This episode is sponsored by
the Side Hustle Starter Kit.

Episode 10: The Washington Post's Austin Graff On Boundaries & Balance in the Digital Age

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Austin Graff leads talent marketing, brand, and social media for The Washington Post and is a contributor to On Parenting, news, advice, and essays for parents from The Washington Post. Prior to joining The Washington Post, Austin led digital, social, and influencer marketing for Coca-Cola’s Honest Tea brand, America’s #1 organic iced tea company. He started out his career leading social media and celebrity relationships for International Justice Mission, the largest human rights organization in the world. After growing up in Russia and Kazakhstan and attending boarding school in Germany, Austin came to the USA for university. He now proudly lives in Washington, D.C. with his wife, baby daughter, and two roommates.

In this episode, Austin talks about his career at The Washington Post, Honest Tea, and International Justice Mission. He also unpacks his unique philosophy of living with roommates while parenting, his time management hacks, and how he cultivates boundaries and balance in his life. 

Episode Highlights

"There’s a verse in the Bible that says if you show you can steward the small things, you will be given bigger things, and that’s the common sentiment to a lot of faiths and people around the world. I found that to be true as I was trying to work my hardest at an entry-level job and not always dream about what’s next and feel entitled that way. I think that holds people back in their careers. I went through that one door with that mentality and tried to work hard and hustle and give my best, even if it was copying papers, and that led to even more trust and responsibilities."

"The moment I’m with my wife or daughter or friends, I try to put it [my cell phone] away. I’m not perfect at it, but it’s my intention for most of the time so that I’m present with people. If someone needs me, they’ll know how to get a hold of me and call. Most likely, if someone texts or emails or sends a Slack that means it’s not as urgent as a phone call, so that’s really helpful. That’s one of my rules – to not be on my phone a lot around people. Being a father has helped because I don’t want my daughter to see that I’m more interested in this shiny object than her."

"I’m really good with tasks and organizing them on my day-to-day calendar, while she’s [my wife] really good at the strategic thinking behind how we should structure our time. We’ll often talk about 'What are our priorities? What are we driving toward?' and making sure all our tasks and how we spend our time add up to that. Recently we went through an exercise where we both went and wrote down our priorities, both individual, and then with my wife Teresa as a family and saw where they are in line and just had a discussion about it. We came up with our top three priorities for this season of time and made sure that most of the things we do ladder up to those priorities." 

Connect with Austin on Instagram and Twitter.

Connect with Hilary on Twitter, Instagram, and Facebook.

This episode is sponsored by
the Side Hustle Starter Kit.

Episode 9: Digital Nomad + Freelance Writer Susan Shain

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Susan Shain is a freelance writer and digital nomad who's been traveling around the world since 2008. She's written about personal finance, travel, and food for outlets like The New York Times and CNN, and does content marketing writing for businesses of all sizes. She's also the founder of WhereToPitch.com, a website for freelance writers, and author of a pay-what-you-want eBook called "The Ultimate Guide to Seasonal Jobs: How to Have Fun, Make Money, and Travel the World."

In this episode, Susan shares how she has made a living living working in locations all over the world. She shares her tips for breaking into seasonal work and freelance writing and why community is a critical component of self-care for digital nomads and seasonal workers alike. 

Episode Highlights:

On Seasonal Jobs:

“You get to make all kinds of new friends. You bond intensely and you get to have a lot of fun by being outside and doing group activities and it offers a really affordable way to travel the country and live in these incredible places that people pay to vacation.”

“My biggest advice would be don’t wait. I talk to so many people who say “I wish I could do that” or “I should have done that” and sometimes I’m blunt with them and I say ‘why don’t you?’”

On Negotiating While Freelancing:

“If somebody offers you something, counter with a little bit more. Of course, when you’re first building your clips you might not be able to command a high rate, but most people are expecting you to negotiate just a little bit and you can always go back down. If they say “no, we really can’t afford that” then you can go back to the original rate, but at least you always asked.”

Recommendations from Susan:


The Art of Nonconformity by Chris Guillebeau

Connect with Susan at SusanShain.com and on Twitter at Susan_Shain.

Connect with Hilary on TwitterInstagram, and Facebook.

This episode is sponsored by
the Side Hustle Starter Kit.

Episode 8: Personal Finance Expert Lisa Rowan On What Every Millennial Needs to Know About Money

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In this episode Hilary brings Lisa Rowan, millennial finance expert, all her burning questions about budgeting on multiple income streams, what millennials need to know about saving, and the finance trends everyone under 40 should be paying attention to.  

Lisa Rowan is a senior writer and on-air analyst at The Penny Hoarder, one of the largest personal finance websites in America. She also cohosts Pop Fashion, a top-rated weekly podcast about the business of fashion and culture.

A former full-time freelance writer and vintage shop owner, she is well versed in the gig economy and the small-business landscape. Her financial advice has been featured in Women’s Health, Family Circle, Refinery29, Real Simple, The New York Times, and NBC News.

Episode Highlights:

“37 percent of millennials have less than 1000 dollars in savings and 12 percent of millennials have no savings at all.”

“Your money situation is as unique as you are to the next person.”

“If you’re trying to meet goals by paying off debt to start, you really need to be resilient and dedicated and you have to know there’s a big light at the end of the tunnel.”

Recommendations from Lisa:
Get Money by Kristin Wong
Broke Millennial by Erin Lowry
Planet Money

Connect with Lisa on Twitter and Instagram @LisaTella.

Connect with Hilary on Twitter, Instagram, and Facebook.

This episode is sponsored by the Side Hustle Starter Kit.

Episode 5: App Creator & Inc. Columnist Damon Brown

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Inc. magazine columnist, creator of the app "Cuddlr," and author Damon Brown joins Hilary to talk about how a social media sabbatical helped his business boom, how to create passive income, and why it's critical for creatives to find their 'why.' 

Author & Time Management Expert Laura Vanderkam On How to Feel Less Busy While Getting More Done


Author and productivity expert, Laura Vanderkam shares some practical strategies from her new book Off the Clock on how to feel less busy while getting more done. 

Laura Vanderkam is the author of several time management and productivity books, including Off the Clock, I Know How She Does It, What the Most Successful People Do Before Breakfast, and 168 Hours (which I loved). Her work has appeared in publications including the New York Times, the Wall Street Journal, Fast Company, and Fortune. She is the co-host, with Sarah Hart-Unger, of the podcast Best of Both Worlds (which I love). She lives outside Philadelphia with her husband and four children, and blogs at LauraVanderkam.com.

Hustle Hack: Try planning your week on Friday afternoons. Most of us are pretty checked out for the weekend by this time of the week. It’s hard to get productive work done then. Why not use that time to plan and prioritize for the week ahead? That way when you get back to your desk on Monday morning you won’t feel scattered trying to figure out what is most important to tackle. You’ve planned your week already. 

Moment of Grace: Each week make a list of priorities for the following week in three categories: career, relationships, and self. Look over your calendar and see where you can drop these priorities in. It’s easy to make a list of priorities for work but it’s critical to also think through priorities for yourself and your relationships. You can even add subcategories including your spiritual life, health, and spouse, for example. 

Connect with Hilary on Instagram,TwitterFacebook, and LinkedIn.
Subscribe to receive strategies to grow your productivity, creativity, and career.

This episode is sponsored by the Side Hustle Starter Kit.

Episode 02: Broadway Actress & Author Alexandra Silber

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Broadway Actress & Author Alexandra Silber has created a career as a stage and television actress, novelist, memoirist, singer, and educator. In this episode she shares her approach to her career as a buffet rather than a ladder and shares how her life came to a full stop when she neglected her health.

Episode 01: Startup Founder & Networking Expert Molly Beck

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Hilary sits down with blogger turned tech startup founder & networking expert Molly Beck to hear about Molly's podcasting startup, Messy.FM, her book "Reach Out," how Molly implements self-care into her routine, and her tips for aspiring entrepreneurs, podcasters, and writers.