The hosts of this hot podcast on the key to bootstrapping your business

Got a side hustle? Even a little one? But do you dream of turning it into your full-time gig someday? Or maybe you are freelance or aspire to be?

Well, then you need the top-ranked Being Boss podcast in your life. Hosted by Emily Thompson and Kathleen Shannon, authors and “business besties,” they dig into the mindset, habits, routines, boundaries, branding, marketing tactics, business strategies, systems, and processes that help you make money doing what you love. And they would certainly know as Thompson founded Indie Shopography, a design and strategy studio for online entrepreneurs, in 2009.

Emily has worked to help makers, coaches, and designers develop an online business model, strategize and launch websites, and grow their online business and Shannon is co-founder of Braid Creative, a boutique branding agency, and consultancy for entrepreneurs in the design, media, art, food and lifestyle space. In addition to their own personal knowledge, they have interviewed some amazing people that also have some pretty insightful things to say including Brené Brown, Marie Forleo, Danielle LaPorte, and Mike Michalowicz of Profit First.

And if you happen to be in the small percentage of the population not listening to podcasts they luckily just wrote an awesome book full of their best tips, strategies, and insights, also called Being Boss: Take Control of Your Work and Live Life on Your Own Terms (Running Press).

Each chapter in their interactive guide covers one of the foundations of Being Boss. From being in the right mindset and having the confidence necessary to get the work done; setting boundaries to be able to prioritize and not feel overwhelmed; creating habits and routines that set one up for success; finding a wolf pack to support and encourage all endeavors; to, of course, making sure that work doesn’t define one’s life, but allows you to enjoy it on our own terms.

The book includes practical checklists, write-in worksheets, to-do lists as well as bucket lists, and step-by-step methods for creating visual goal-setting systems that work, which really make it more of a daily, holistic practice that gives creative entrepreneurs the tools they need and not just another business book to put on your shelf.

Ladders was lucky enough to get the following book excerpt from the chapter titled “Invest in Yourself”

You’ve heard it a million times: you have to spend money to make money. But we’re not buying it. We have bootstrapped our businesses and grown our teams with zero debt. We’ve paid our bills since day one and have made it a priority to invest in ourselves along the way. And trust us, there is no windfall, private investor, trust fund, or sugar daddy paying our way. The most talented and innovative entrepreneurs we know have managed to expand their capacity for success by working with what they’ve got and getting creative within the constraints they’ve been given. They’re not trying to buy their way to the finish line, and neither should you. Money certainly makes some things easier, but there is no amount of cash that will guarantee success. However, you can invest in yourself along the way, in a way that doesn’t break the bank and gives you little boosts of fuel that will help you level up your game.

Anytime you make a purchase in your business, it’s important to ask what the return on investment is — how will the benefit justify the cost? In other words: How will this purchase help me make more money? And how much? By asking these questions, you can begin to figure out when to invest in your business with money and when to invest with do-it-yourself sweat equity and work with what you’ve got.
Technology and tools: Investing in tech and tools that help you work with more speed, quality, efficiency, and craft will enable you to create better work in less time. Now, that said, you do not need to purchase every shiny new toy that comes on the market. If you’re strapped for cash, make do with what you have and only invest in tools you use every single day. For example, don’t buy the newest iPad with dreams of doing hand lettering on it if you’re not even practicing on paper first. Don’t buy a fancy new microphone for the podcast you don’t yet have. Start by creating with the tools you already have until they clearly impede your progress—and THEN invest in the tools and tech that will help you take things to the next level.

Health insurance: When you work for yourself, paying for your own health care is like paying taxes. You may feel it a little harder because you don’t have an employer automatically withdrawing it from your check for you, but paying for it yourself shouldn’t be a deal breaker when it comes to making the decision to work for yourself. Plus, as a creative entrepreneur, you have potential to make even more than what an employer could pay you! It’ll all come out in the wash.

Your office space: One of the best things about being a creative entrepreneur is the location independence that comes with the nature of our jobs. You can be a legit professional from home, a coffee shop, a beach, or your own studio space. We’ve tried it all, and no matter where we’re working from, we’ve found one thing to be true: creatives need to feel at ease in their space no matter where they’re working. Invest in the essentials that will inspire you while you work — whether that’s a delicious-smelling candle, a standing work desk, a really comfy chair, or a bunch of plants and a co-working kitty cat.

Conferences and retreats: Most creatives don’t travel enough because they decide it’s a frivolous expense. But there is nothing like attending a conference or retreat to establish genuine connections that will feed your career with clients, referrals, and countless opportunities. Travel isn’t an expense — it’s an investment. When you travel for business, be sure to set an intention, “turn on your taxi light,” make new friends, and see the world while you’re at it.

Coaches and masterminds: It’s easy for self-reliant solo entrepreneurs to get used to working in a bubble. Investing in a great coach or quality mastermind can counter that tendency by introducing you to new people, ideas, concepts, and strategies, and those connections will more than pay for themselves.

Housekeeping and day care: Listen, you only have so many hours in the day. When you’re not working on hustling out your business or growing your side-hustle, the last thing you want to be doing is mowing your lawn, scrubbing your toilets, or trying to keep your child entertained while growing a business. Outsourcing chores and child care will give you the headspace and time to not only make more money in your business but devote more quality time outside work to doing the things you love and spending quality time with those you care about most. And if you feel guilty about outsourcing these responsibilities, remember that by doing so you’re supporting the livelihood of others who are trying to make a living by delivering value to your life, too.

Growing your team: If you’ve been working for yourself for a while, hiring your first employee will feel as scary as the time you quit your day job—but if you’re overwhelmed by all the hats you’re wearing, growing your team to handle tasks efficiently will be a worthwhile investment. Also, you can dip your toe into growing a team by hiring help as you need it on a project-by-project basis.

Reprinted with permission from BEING BOSS © 2018 by Kathleen Shannon and Emily Thompson, Running Press