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11 Things I Wish I Knew When I Started My Business

You’ll probably run out of money, but you’ll learn to accept yourself in the process

Working. Or maybe ordering wine off the internet.
“A lot of people like to fool you and say that you’re not smart if you never went to college, but common sense rules over everything. That’s what I learned from selling crack.”
 — Snoop Dogg

My name is Stephanie St.Claire, and I’m an unfunded entrepreneur. I’ve been in business for seven years. To get here, I engaged in my own personal and tenuous renaissance (uh… divorce) and rediscovered my Core Purpose. In other words, I grew a pair of ladyballs, launched a business, and figured out how to turn my efforts into profit.

But there was a lot to learn, some of which wasn’t covered in Who Moved My Cheese?


Throw these four rockstars into a blender, and you’ll have a composite sketch of me in the first three months of my business:

Glitter was literally shooting out of my eye sockets as I quit my PR firm job. Full of optimism, living in New York City, and surrounded by a tribe of friends who were also launching businesses, I felt it was the perfect time to make a bold move to entrepreneurship. I was now officially Living My Dream and Working For Myself, which meant I was in charge of my financial destiny and Captain of My Promising Future.

Luckily, my initial hyperoptimism buoyed me whilst, oscillating between euphoria and despair, I was slowly but systematically forced off The Magic School Bus and onto the S.S. Battleship Long Haul.

I was a quick and eager learner, but despite the hours of webinar watching, countless Friday nights pumping out site copy, and teaching myself everything I could about HTML, there were just some things I didn’t get. I had to fall on my ass to procure the “master’s degree in life survival” every entrepreneur earns on their “journey.” (Yes, those are bitterly gesticulated air quotes.)

Somehow, through that process of acceptance, while you’re busy putting yourself out there in spite of your flaws, your weaknesses will transform into assets.

Here are 11 things I wish I knew when I started my business. I hope they will save you some time, and at the very least, some anguish because — experience is a good teacher here — the sodium from your tears acts as a corrosive melting agent on all brands of premium ice cream (though it does make a superb saline for your dirty martini). Cry over a cup, oh fathomless bird of preneurial gumption!


1. Running the business is your first priority.

Your success (and financial stability) will come from expertly running your business — not writing copy, rebranding your client’s website, teaching yoga, podcasting, or making jewelry. In other words, you will spend 15 percent of your time doing what you love (your gift, in my case coaching and writing) and 85 percent marketing, administrating, selling, strategizing, and answering a shitload of email. Survival will hinge on how quickly you adopt this role of business owner first, creator of pretty things second.

This sucked for me because I wanted nothing to do with running a business. I just wanted to be a writer and a life coach who wrote and coached all day. I didn’t get it.

2. Ready to meet your soulmate? It’s you.

Entrepreneurship is the most life-changing relationship (like marriage or parenthood) that a person can have. You will be confronted overandoverandover with your fears, insecurities, crappy excuses, limitations, justifications, shitty integrity, and inefficient time management. The standard you held yourself to in the workaday world was good enough then, but it won’t be good enough to run your own business.

You will learn to accept yourself through all this because, in order to get up every day and create a profit, you will have to. Somehow, through that process of acceptance, while you’re busy putting yourself out there in spite of your flaws, your weaknesses will transform into assets. Slowly but surely, you will fall in love with yourself. Not in the over-hyped “Self Love 2018” way, but in a quiet way that sneaks up on you after witnessing a thousand splinter-sized moments of transcending the baser aspects of yourself.

3. Your trajectory for success will take as long as everyone else’s, even though you are special and brilliant.

I heard the “two-year rule” when I started my biz, but I was confident I could do it in six months. I believed with every fiber of my glittery, go-gettin’ heart that my work ethic (15-hour days, seven days a week) — along with my talent, skills, and personal magic — could rip a path to accelerated success. This was a leap of faith, one that was worth some express lane juju points from Heaven.

Jesus had other plans.

4. Running out of money is a common part of the journey.

You won’t expect it, because you prepared for the long haul. You secured a business loan, or got some investors, or sold your house (cough, cough), or have one year’s worth of savings and have planned accordingly.

But then all of the sudden, amidst the puffy clouds and blue skies, your little twin engine Entreprenairplane will sputter, the needle on the gas gauge unexpectedly plummeting to zero, and you will only have one choice: land your plane on the wild, abandoned air strip called Bank Balance: 14 Dollars. And this will be the last place you ever thought you’d crash land, because didn’t you pass this test on No More Sephora Island?

The good news is this is a rite of passage that will launch you into the League of Business Badassery in which, once you are out of the money hellhole, you will be unstoppable. You’ve been to the baddest prison there is, looked down the barrel of your worst fear, and stood your ground. You didn’t quit. You got up the next day, and you wrote your next post, created your next offering, and answered the email with zero dollars in your bank account.

There is nothing more beautiful than running out of money and realizing that you are doing your work because you’ve got the guts to push through your worst fears when there is no evidence of security. You really, truly love what you do, and you’d do it for free if you had to. Irony is a sassy bitch, isn’t she?

5. Build a hybrid stream of income.

Take a second job if it will give you peace of mind. Please don’t feel like you’re failing at your business — learn from my mistake. I was so resistant to “dividing my focus” or taking any action which I interpreted as undermining my commitment to being a successful writer and coach. Do you see the hellish mousetrap that was? I really thought that by making a Plan B, I was telling the Universe I wasn’t 100 percent serious about my success. I created a worse problem by allowing financial stress to gut me of my sanity.

If having a steady stream of part-time income would be in service to your peace of mind, do it.

I finally came to terms with the fact that I was being obnoxiously naïve about how money, peace, survival, and timing all work together, and I got a second job. By doing this, I supernaturalized my own path to freedom and self-sustainability. And since I wasn’t freaking out about money anymore, I liberated more creative real estate in my brain to apply toward my business.

6. Read Steven Pressfield’s Do the Work!

The biggest challenge you will deal with in running a business is your own resistance. Before you study anything about marketing, social media, money, or time management, read this book. You’ll be treated to gems like this:

Remember, our enemy is not lack of preparation; it’s not the difficulty of the project or the state of the marketplace or the emptiness of our bank account. The enemy is Resistance. The enemy is our chattering brain, which, if we give it so much as a nanosecond, will start producing excuses, alibis, transparent self-justifications, and a million reasons why he can’t/shouldn’t/won’t do what we know we need to do.

7. Spend less time researching, more time doing.

Researching, studying, and reading other people’s blogs is a form of resistance. In order to get clarity, you must act. Clarity does not come by learning more — it comes by jumping in with your instincts and putting yourself out there, even if you don’t know exactly what you’re doing.

Block out the distractions (turn off the phone, social media, and email notifications) and take inspired action that feels tangible and measurable. Set a timer for 25 minutes and go to town on a task. Do not look up. Do not go to the bathroom. Do not cruise the fridge for cheese sticks. Get something done, despite the fact that at times you will feel like you are pissing into the wind. Piss into the wind four times a day, and you’ll make a difference in your bottom line.

Set a timer for 25 minutes and go to town on a task. Do not look up. Do not go to the bathroom. Do not cruise the fridge for cheese sticks.

8. Only say yes to collaborative projects that are hell yeses.

Scrutinize any joint project carefully and qualify the person you’re collaborating with (even if they are your friend and have higher social media stats than you). Get everything in writing before you embark on the project, with a clear division of labor and deadline dates. You will most likely be splitting the profits, so have two numbers in your head: The number you need to make in order to pay for your time, and the number you would like to make. Set the first financial deadline early so that you both have the freedom to walk away if the project isn’t going to be profitable. Have a transition strategy in mind so in case that happens and one of you wants to continue on with the project, there is a way to pass the baton gracefully.

Summed up: communicate about everything — even though you’re friends, even though you love each other, even though you trust each other, even though you’ve worked together at XYZ Company, because projects have a way of going sideways and making everyone a little custodial and overreactive.

9. You must devote time to becoming a brilliant marketer.

I know you just want to spend all your days making hipster sarsaparilla-scented mustache wax, or needlepointing edgy throw pillows for Etsy, or writing your YA zombie novel, or life coaching entrepreneurs to stratospheric success, but if you don’t spend time marketing you will not make money.

This was my biggest weakness when I started. I thought marketing meant slimy sales letters with big arrows and opt-in boxes, and I couldn’t! I wouldn’t! So I put my head in magical fairyland sand, stubbornly insisting that my customers would be tractor-beamed into my budding practice by the pulsating, heavenly light that radiated from my vision boards and four blog posts.

And then I ate canned food and spaghetti for a long, long time.

What rescued me? Knowing what marketing personality I embody. There are three main types:

  1. The Guru (Brendan Buchard, Danielle LaPorte, Gary Vaynerchuk, Marie Forleo, Tony Robbins), whose marketing boldly states, “Listen to me. I have the answers.”
  2. The Wisdom Advisor (Brene Brown, Chris Guillebeau, Marianne Williamson, Dave Ramsey), whose marketing feels like, “This is what I’ve found to work best. Let’s brainstorm together, and I’ll help you find out what’ll work for you.” And finally,
  3. The Connector (Oprah, Jonathan Fields, Mark Zuckerberg), who connects people with other people and resources.

Once you have figured out your marketing personality, selling to your customers will be a thousand times easier because you will be working within your natural vibe. Learn how you like to market and stick to that. Do it consistently and often. Even if you hire a pro, you will be doing some marketing yourself. Keeping your website fresh and current is essential, so also learn how to work WordPress and HTML code. You will be in the guts of your website a lot.

10. Email will be your new best frenemy.

Your inbox will explode. You care about everyone, but you can’t help everyone. Read: Not everyone is your customer. Your inbox will be a jumble of people who want to say thank you, people who want free stuff, and people who want your services. Your job is to quickly discern who’s who and respond in the most appropriate way.

Shorten the email back-and-forth as quickly as possible with potential clients. If your business is a consultancy where you are selling your time, I recommend having two form letters on hand that you can customize to the occasion: one for potential customers and the other for non-potential customer.

If you don’t spend time marketing you will not make money.

For Your Customers: Acknowledge the situation, request, or problem and extend an invite to a 20-minute call. Include your available dates, times, and phone number.

For Non-Customers: Acknowledge the situation, request, or problem and provide other resources, practitioners, blogs, or articles that would be a splendid fit.

I love connecting personally with my clients. In this area of business, I am 1997 all the way. I pick up the phone and talk to them live. I schedule all the calls on one day or after my regular client sessions. I have found this to save a colossal amount of time. In a 20-minute phone call, I:

  • Find out their history and current issues.
  • Explain to them how coaching works and pricing.
  • Ascertain if we are a fit and if they are ready for coaching.
  • Answer any of their logistical questions.
  • Give them a personal sense of what it would be like to work with me on the phone (my tone of voice, cadence through the call, etc.).
  • Process the invoice.
  • Set up the first session.

Do you know how long that would take back-and-forth by email? Anywhere from five days to a month. Do not screw with your own time.

11. This last tip is a hodgepodge.

Do not work your business seven days a week. Cover your legal ass from day one. From time to time, forget everything you know about the “right way” to run a business and run it like a neighborhood lemonade stand. Do not price your offerings around your personal ability to pay for it — you are not your ideal customer. Work out perplexing issues in your business, and it will resolve problems in other areas of your life. Connect with other entrepreneurs and set up a Skype brainstorming session (with wine). Take a walk around the block every day at lunch. And lastly, if you want to be smarter in business, follow everything these two people do: Gary Vaynerchuk and Regina Anaejionu.

Originally published at stephaniestclaire.com