Stories We Tell Ourselves as Entrepreneurs

The stories that we tell ourselves as entrepreneurs,
and how to flip the script  

Whether you own a thriving business with multiple employees, are working independently with a range of clients or are in the process of creating a company, you are an entrepreneur. Maybe that’s obvious, but for me, I’ve struggled with calling myself (a freelance writer with no employees) an entrepreneur. Call it imposter syndrome, but it’s a thing for me and it may be for you too. Now that we’ve got that out of the way, let’s get into it. 

Before stepping outside the bounds of the 9-5 life, I fantasized about working for myself. I imagined days full of freedom, running my own show, drinking latte after latte working from cute coffee shops. Don’t get me wrong, there have been many days like this. In general, entrepreneurship has been the wildest emotional roller coaster I have been on to date. Some days are blissful, inspiring and empowering, while others are lonely, uncertain and quite frankly, terrifying. While I don’t seek to speak for entrepreneurs as a whole, I know enough of them to know that these bad days are often a result of a conventional narrative rut we allow ourselves to get into. Scary stories, if you will. 

Below are a few stories that play in my head from time-to-time and have influenced a number of decisions I have made as an entrepreneur. In fact, these stories became so loud at one point that I quit being an entrepreneur all together for awhile—but I’m back, baby! I am highly aware that every business owner comes to the table with different sets of circumstances and these fears are very real. While there may not always be an answer, I’ve offered a few shifts in perspective and behaviour I’ve taken to flip my scary entrepreneurial stories into something more actionable and positive. These shifts have saved me over and over, and I hope they give you a little something too. 

I won’t have enough money! I will be broke! How will I ever pay my rent, save some $$, enjoy my life and maybe buy a cute top once in awhile?!

This is a juicy one that everyone, entrepreneur or not, can relate to. The fear of financials is what most commonly prevents people from taking the leap into entrepreneurship or leads them to forgo the freedom for a steady paycheck. There’s no magic wand to wave because unfortunately, money is a must, but here’s a few things I like to tell myself when the dolla dolla bills narrative is taking up too much space:

• It’s ok to say yes to something that isn’t your dream project for the sake of padding your bank account. If this is what you need to feel stable, then go for it. This will help to clear the space for work that not only lights you up, but pays the bills.

•  Money is always coming and going. If I hold too tightly to the notion that I don’t have enough, it’s hard to get out of the scarcity mindset. As soon as I let it go, things often start to fall into place. 

• It’s also ok to simplify your life while you are establishing yourself as an entrepreneur. What I mean by this is, you can spend less on salads, fitness classes and coffees. I did this for a few months when I first started freelancing and it actually felt amazing. Living with less is beautiful and lets you focus on creating a vision for what you want for your future and your business. 

I won’t ever find work. No one is reaching out to me with projects that excite me or reaching out at all. I will fail. 

We choose to become entrepreneurs and launch businesses because our hearts (and egos) believe what we are up to is worthy of  peoples’ time and attention. Not surprisingly, when business isn’t booming or the work we want isn’t coming our way, our egos take a hit. I struggle with this constantly, but I will leave you with this quote from the queen herself, Oprah Winfrey. I go back to this always and it seriously (seriously!) works:

“Don't hold anything too tightly just wish for it. Want it. Let it come from the intention of real truth for you and then let it go. And if it's supposed to be yours it will show up and it won't show up until you stop holding it so tightly” 

I will be lonely and sad and in my housecoat all day! I will go stir crazy without friends or co-workers to inspire me, make me laugh and eat snacks with. 

I could equate working from home every day as an entrepreneur to eating cake for breakfast  on the daily—on day one it feels good, day two maybe still feels tasty, but by day three your stomach hurts and you need a change. The reality is, if you stay in your pj’s and don’t leave your couch every day, you will start to feel lonely. If you are anything like me, you need the energy of other people and spaces to feel productive and inspired. So, try a co-working space, a coffee shop or a public library. Bottom line—make a conscious effort to get out of your house at least a few times a week and you’ll be just fine. 

Clients are so annoying—endless feedback, not paying on time, the list goes on! Being a full-time employee would make my life so much easier.   

Yes, managing client relationships and the host of intricacies that come along with being a successful entrepreneur can be undoubtedly annoying. What I try to always remind myself when I get into this thought spiral is that every path (full-time, part-time, contract, whatever) comes with its share of stuff you’ll hate. It’s comforting to know that when things get tough, as an entrepreneur I have the freedom to make decisions to improve the situation—whether it’s setting a boundary with a client, renegotiating a contract or stepping away from a project. You don’t even have to ask the boss, because the boss is YOU. 

I am going to burn out. The ebbs and flows aren’t sustainable for me. 

I am an anxious person who is often afraid to say no. This combined with the financial fear narrative means that I have found myself in a burnout or near-burnout situation too many times. The truth is, burnout can happen whether you are an entrepreneur, a CEO of a global company or a new mom. The best we can do is take small steps to support our mental and physical health before it’s too late to catch a burnout meltdown. For me, this looks like saying no (even though it KILLS me), reading lots of books, making time for movement that feels good in my body and sleeping at least eight hours every night. 

You may by now have emerged from your entrepreneurial fear vortex and are feeling clearer. There’s no way around it—this path isn’t for everyone and takes a whole lot of grit and gusto. But, when it’s good, oh man is it good. Be like Oprah, let it go and trust that your entrepreneurial path will unfold as it should.