This fall, Clementine, my Brick + Mortar, turned 5. I celebrated. I took stock of the friendships, partnerships, and mentoring I had done. I felt proud and happy. Then, like a punch in the gut, I suddenly felt worn down - heavy with small business fatigue. I imagined working for someone else; letting them make decisions, and giving me a steady paycheck. I left 2015 with two weighty, honest questions:  What do I want to do next year? And, if it’s this, How can I do it really well? ~ Emily of Clementine
Illustration Emily McDowell for Oh So Beautiful Paper
As busy, creative entrepreneurs how do we confront questions of doubt? Like many of you, I have several side-hustles. I love them just as much as my main gig, but I often wonder where and how to focus my energy to be efficient. Last year, I started a styling and creative consulting partnership, I began offering creative consultation, I continued to write here (xo), partnered with Etsy on some of their new wholesale endeavors and, last month, decided to organize creatives to take a stand against gun violence. I love starting new things and having variety to my work. I love how these things relate to each other, but they pull me in different directions. How do I do all of them well?
2015 was about gathering advice and resources to make my business bloom, but I admit, it’s far easier for me to daydream up new ideas than to put them into practice. I’ve been lucky to befriend some incredible small business owners, so I began 2016 by making time to talk to my cohorts about the nitty gritty of what’s next for me. I also relied heavily on the greater small business community, especially on podcasts, to help me think through many of my small business dreams and plans. This year, I need to dig in and create a structure to help my business plans flourish. I wanted to start 2016 by sharing a few of my favorite podcast episodes, many of which I’m revisiting as I plan for the road ahead. I hope they help you move you through your own stumbling points and give you a boost for 2016! (I’d also love to hear your favorites!)
After the Jump, has been, without a doubt, one of my favorite podcasts. Hosted by Design Sponge creator, Grace Bonney, this podcast stopped airing a year ago, but there are 100 incredibly helpful episodes. My favorites include: Episode 6 Meg Mateo Ilasco and Mom Inc. (deleted from the web, but still available on itunes!); Episode 20 Becoming your Brand Episode 39 Raising the Bar; Episode 90 Genevieve Gorder returns.
Magic Lessons is the creative weekend getaway we all dream about in podcast form. This short follows up on Melissa Gilbert’s work with her recent book Big Magic. Each episode comes in two parts – an interview with a creative person who is stuck and then a conversation with one of Gilbert’s co-horts about advice for that person. I adored this short series, but Cheryl Strayed’s advice in episode #2 Pursue your passion like a mofo and Brene Brown’s take in the final episode, Big Strong Magic, were the food I needed to keep my creative heart beating last year (do listen to the complimentary episode for each or they won’t make sense!)
Being Boss is a podcast for creative entrepreneurs hosted by Emily Thompson and Kathleen Shannon.  This is one of my regular listens (thanks to Kristen’s recommendation at the August NYNOW). I especially loved episodes #4 How to Be Boss When You’re Afraid of Failing and episode #53 The Value of Staying Small.
#girlboss radio. Launched after the crazy popularity of Sophia Amoruso’s book, #girlboss, these conversations are refreshingly honest with a kick of irreverence. They’re all fun, but for business, I really liked Episode #4 Sheree Waterson, CEO Nasty Gal.
Profit Power Pursuit.  Tara Gentile asks delightfully pointed questions which lead to real, detailed answers from her guests. I haven’t listened to all of them, but especially enjoyed these two so far: Episode #3 Megan Auman; Episode #8 Keri Chapin.
The Lively Show. Jess Lively is effervescent and upbeat, even when tackling difficult topics. I enjoy the episodes when she digs into tougher life stuff, and interviews grounded, deep women. I especially enjoyed #58 Using Values to Thrive in Work and Family with Tina Roth Eisenberg; and episode #107 Quitting a Full-Time Business for More Joy with Melissa Gruntkosky, which explores the extremely important question of when quitting our passion project may be the best thing for our lives.
Smart Creative Women. Hosted by Monica Lee, there are some wonderfully extensive interviews with creative women. Two of my favorites include Lisa Congdon: A Creative Journey and Emily McDowell’s Amazing Adventure.
Start Up – This podcast is all about the making of Alex Blumberg’s podcast company, Gimlet Media. The transparency and awkwardness in this series is refreshing and compelling. Start with episode #1 How Not to Pitch A Billionaire and see if you want to listen on…
Iron Curtain Press’s The Dream Is Free Print means one thing when you’re dreaming, and another when you’re years in.
We’re experiencing a bit of a golden era of entrepreneurialism. Starting your own business is applauded. Quitting your day job is glorified. Running your own thing is great. But we’re not all cut out for it, and even those who are generally deserve far more support than we’re receiving. I know it’s not time for me to sell the farm (or the store in this case!) but I’m digging in to my resources, I’m making time for tough conversations with fellow business owners (and my family) and I’m genuinely looking forward to some change this year.
What about you? What’s ahead in 2016? What are your stumbling points as a small business owner and where do you turn to overcome them?
