10 Lessons from My First Decade of Entrepreneurship

Ten years ago, I filed for my first business license. It’s been a crazy, intense, rewarding, overwhelming, exciting and unbelievable ride so far. Here are my top 10 lessons from my first decade of entrepreneurship.

#1 Be Comfortable with Money

Get comfortable talking about it, handling it, asking for it, managing it, budgeting it, thinking about it, receiving it, spending it and creating it. Without money, a business is simply a fun project. The IRS even has a rule that you are allowed to claim a business loss on your taxes for three of the last five years. If you’re over that, they automatically classify your business as a hobby.

One of the biggest mistakes I made as a young entrepreneur was to ignore this area of my business. I discounted all my prices, agreed to terrible payment terms, let invoices lapse, failed to budget or account for my expenses and refused to keep regular accounting for my tax preparation. I avoided it like the plague because if it wasn’t in my field of vision, it simply didn’t exist, right?

Add to that yearly panic before tax prep, losing loads of money, over spending on expenses and forgetting to cancel memberships. Now I have created a phenomenal relationship with money. Not only has my wealth consciousness expanded, but I am also doing weekly budget checks, statement reconciliations, tax planning and forecasting.

Tip: Check out my favorite book about wealth consciousness, The Science of Getting Rich by Wallace D. Wattles, and implement a weekly Money Date.

#2 Say ‘No’ More Often Than You Say ‘Yes’

In the beginning, it’s common to say yes to everything because you never know where opportunity will come. But this becomes exhausting very quickly. I can’t tell you how many events I attended or showcased at that were misaligned with my demographic.  My first business coach called this the ‘Spray and Pray’ method—where you put yourself everywhere, give your business card to everyone, attend every event and do mass, un-targeted outreach hoping and praying that one of them would pan out.

Knowing when to say yes is an art form. Get clear on who your people are, learn where they hang out and what events they attend. Then learn to tailor your outreach and output to be in alignment with that.

Tip: Be smart about focusing your energy and attention into what will create results rather than constantly hoping that every opportunity will result in instantaneous success, fame and riches.

#3 Know Your Zone of Genius and Outsource the Rest

In the beginning, it’s good to learn everything. You’ll want to know how all the cogs in your business work before outsourcing them to people. But the trap of, “It’s easy. I don’t want to pay someone to do it, I’ll just do it myself,” is one heck of a trap. I still fall into it. Just yesterday I was hesitating about hiring a transcriptionist because it’s mindless work that I can do myself. The problem is, it’s keeping me from focusing on the important tasks such as client generation.

What are you good at? Is it strategy or execution? Are you a big picture or a details person? If you’re a big picture person and you’re spending all of your days focused on funnels, emails and overall execution, you will reach burn out way too quickly.

Tip: Know yourself. Know your strengths. Know what lights you up and excites you. Find a way to do it more often than not.

#4 Know When to Let Go

Sometimes saying goodbye to a business is just as important as when you created it. I have officially closed more businesses than I have kept alive. And that’s a good thing. I have a very important rule: when it stops feeling good, it’s time to release it.

Towards the end of my fashion business, I got home every night feeling like I had run ten marathons on a hamster wheel. I was expending hordes of energy, beating my head against the wall and getting nowhere. Until I remembered something I said when I first started the business: “Fashion is supposed to be fun. Too many people take it too seriously. When I stop having fun, I’m committed to getting out.”

It was just a few months later that I closed the business without regrets and without looking back.

Not every business you start will have longevity. The founder of Dollar Shave Club, Alec Brownstein, was recently interviewed on the Unthinkable podcast wherein he said:

All of these projects are worthwhile because they’re building my body of work. So, while a specific project may not have caught fire or made a million dollars or grown into a humongous thing, I view them as pieces of experience even if they don’t succeed.

Tip: Catch the entire episode here.

#5 Never Take Advice from Someone That Isn’t Living the Life or Running the Business That You Someday Desire

Everyone is going to have ideas and advice for you when you become an Entrepreneur. Be very discriminatory about whose advice you listen to. You wouldn’t take advice from a  used car salesman if you were building the next medical technology app.

Tip: Get a mentor, coach or advisor on board, but make sure that they are in alignment with the future vision that you have. Find someone who has created a business of the same magnitude that you desire. What I’m saying is, if you plan to build an empire be sure that you’re taking advice from someone who has built an empire.

#6 Get Used to Putting Yourself out There

I used to know this actress when I first moved to Los Angeles. She had been here longer than me and the city was definitely wearing her down. I listened to her lament day after day about how frustrated she was going to her day job and how discouraged she was that she wasn’t booking any acting roles.

The problem? She wasn’t leaving the house to connect with directors, hosts, writers, and industry people. She didn’t go to industry events. She routinely missed auditions. And when she met someone new, she would introduce herself as a waitress.

If you aren’t willing to root for yourself, why would someone else?

Tip: No one else is going to advocate for you in the way that you will advocate for you. Declare your vision and own it. Start telling people what you’re creating. In fact, tell everyone you meet what you’re doing, who you are and why they should care. Even if it requires baby steps, you need to start somewhere. Believe in the importance of what you’re creating and be unapologetic about sharing your vision with the world.

#7 Learn to Exist in Massive Amounts of Discomfort

The biggest growth—which will also translate into the biggest results—you will ever experience in your life and business is just outside your comfort zone. Entrepreneurship is a daily experiment of a life past what’s easy and comfortable. It’s a continual adventure of expansion and growth that requires you to do things that terrify you.

Allowing your fear response to pop-up every time you are required to do something that scares you will significantly stunt your growth.

Tip: Find a way to set discomfort as your new normal baseline. That’s not to say that you won’t have fear, but it won’t paralyze and delay you from building your vision.

#8 Carve out a Minimum of 30-Minutes a Day for You Time

This is the biggest lesson I have learned over the last 10 years and the one that has created the most sustainable transformation in both myself and my business.

When I started on this Entrepreneurial path, I had zero relationship a higher power, I had no idea who I was and my soul was running on empty constantly because I was giving everything I had without replenishing myself.

Now I devote the first three hours of my day to filling my heart, setting up energy towards my vision, connecting with the Universe and preparing for the day ahead. Some days, it’s the only thing that keeps me going. Without it, my life and my business would still exist in complete chaos.

Tip: Start a daily practice. Try reading Miracle Morning by Hal Elrod if you need some tips to get started.

#9 Develop Boundaries

In the beginning, not only was I working a 40-hour job, but I was coming home and working on my business until midnight—as well as all of my days off. I lived, eat, breathed, and—barely—slept my business.

Implementing boundaries is a game changer. It will streamline your tasks so you focus only on the important ones, and it will force you to remove distractions and be more present in every moment. Imagine if you only allowed yourself a certain number of hours to work everyday, instead of the typically advertised 20-hour per day hustle. You would be forced to narrow down your output and prioritize the tasks that will move the needle forward.

Tip: Know when you need to take a break. Recognize when your effort is beneficial, and when it would be better for you to recharge. Turn your computer off. Put your phone on silent. Spend more time with loved ones.

#10 There Is No One Path to Success

There is no special formula that will catapult you to the top. There are no magic beans. Don’t ever trust anyone that promises you results based on an—insert random number of days/weeks/months—formula to 6- or 7-figures.

There is only one person that knows your path to success, and that’s you. Your work is to uncover it. It’s great to learn from mentors who have gone before you, but that does not mean you should emulate their exact path because yours will inevitably be different.

Tip: Discover and own your power and use it to create YOUR path, no one else’s.

And my last bonus lesson: Enjoy it! People don’t become entrepreneurs to wear the golden handcuffs that corporate life puts you in. Why would you torture yourself this way? If you are only going to make yourself suffer as an entrepreneur, you might as well stay employed and have a steady paycheck coming in!

Here’s to another decade of creating, impacting and growing everyday!

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