How to take the brave steps to be your own bossFeatured

Does fear of the unknowns of entrepreneurship hold you back from taking action? Do you have a dream business that you have been thinking of starting for months or even years? Perhaps, you have cultivated a side hustle that you fear going all-in on. Or even started and closed a business in the past.

This is what you’ve been waiting to hear.

I am a lifelong entrepreneur. From babysitting and tutoring in high school to the first business I started at 25 (it was a boutique photography/party business where I gathered successful professional women for combo LinkedIn/Tinder photoshoots and networking), I am naturally inclined toward the freedom and flexibility entrepreneurship affords me. So much so that for the past six years, I have worked in private practice as a trauma-informed Business Coach for entrepreneurs.

Not only have I made over $1,000,000 in the six years I have been working, but I have also helped hundreds of people start, scale and strategize their businesses, be they service or product-based.

Based on the personal experiences of both my clients and myself, the reality is that the uncertainty and inconsistency of entrepreneurship can prove to be a truly daunting thing to grapple with when you’ve been used to collecting a paycheck on a weekly basis for your entire career. Not to mention, the internal dialogue that will question your capability and resilience while your family and friends ask you things like, “What about having a 401k and employee-sponsored health insurance?!”

As someone with a chronic medical condition (I’m a Type 1 Diabetic) and the dream of making more than a job could ever pay me, I can assure you, I have been right where you are. Motivated, but uncertain about how to quiet the thoughts that make the idea of building a business, nay, empire, feel safe enough to pursue full time.

However, the reality is that the greatest job security you could ever have is being your own boss (because no one can fire you!) and your capacity for making income will never be greater than through the path of self-employment. In fact, a study by UC Berkeley showed that over the lifetime of an entrepreneur vs. a salaried employee, entrepreneurs out-earn their employed counterparts time and time again.

So how do you create safety for your nervous system (and maybe your bank account) while you take the courageous step to being self-employed? The truth is simpler than you think.

Get a side hustle

Most of the anxiety I see in clients around entrepreneurship is related to their perception of safety, not to the reality of their circumstances.

In today’s world, the gig economy provides even more security for entrepreneurs on their journey to financial, time, and location freedom. When I started my business, I did everything from being a nanny to reading Tarot cards at nightclubs to taking on extra work as a personal assistant. I once made $120/hour as a private tutor for college students and was making five-figure months side hustling before my business ever even took off.

I have an entrepreneur’s brain – it was obvious to me to do this. When I work with clients, they get so stuck on the “how” and the viability of their idea that they spiral in existential dread for longer than it would ever take them to acquire a profitable side hustle and get to work on their actual dream. If this is you, this is your sign to get on Upworthy or Indeed or any entrepreneur Facebook group and secure yourself the kind of side hustle that will make your focus not so much on if your business will make money, but on how to best create something of value that people would want to buy.

The issue with putting all that pressure on your business to be your sole source of income when you start is that you are actually the one making yourself feel unsafe. You are hoping so much for whatever you are doing to be successful that the amount of pressure you are putting on it and yourself is messing with your creative flow and efficacy.

Imagine trying to sell a coaching contract or a creative project pitch with the energy of “Please hire me so I can pay my rent!” No one wants to buy that from you! So much of the initial stages of entrepreneurship are about ideation and experimentation. Give yourself the financial flexibility to do that (which, with the gig economy, is more possible than ever) and focus on building a strong business foundation, not immediate profitability.

When you have a financial safety net (which is not a privilege that is afforded to all of us, but can be created by all of us with Uber, tutoring, babysitting, freelancing etc.), your focus becomes more about the business and not your bank account…and this will truly change the quality of the work you put out there.

Don’t get business advice from people who have never had the kind of business you have

It amazes me how eager the loved ones of my friends and clients are to give their unsolicited opinions about their business (and lives). It’s nice, people care about you. However, their own fear about whether or not they would be able to do something like what you are doing is at the root of the (usually bad) business advice they are giving you.

If you want to start a copywriting agency, don’t ask your Aunt Betty who worked at a job she hated for 45 years what her opinion is. People may not agree with, support, or understand your dream…and if that is the case, their opinion is likely going to feed the tiny voice of fear and insecurity that is usually (and understandably) in the mind of every single entrepreneur out there.

It makes sense to have doubts and fears, don’t enlarge them by putting the fears of other people on top of them. You want great business advice? Listen to my podcast. Find a mentor. Hire a coach. Join a networking group of local entrepreneurs. Source your information from a place that has both expertise AND an empowered perspective to offer.

Your mindset is one of your greatest business assets, and it’s okay to protect it when you are starting out. It’s okay to let people know you love knowing that they support you, but you aren’t open to feedback about what you are doing at this time. All great CEOs need excellent boundaries–this is the first place you get to practice cultivating them.

Be innovative and remember – you can’t fail

The truth about entrepreneurship is that it is actually impossible to fail at it. Sure, you can lose money. You could launch a product or a program and no one could buy it. You could try for a few years and experience minimal results. But you can’t fail. The journey of entrepreneurship requires consistent innovation and resilience. Every successful business owner has wasted at least a few thousand dollars on something that didn’t pan out. They’ve received critical feedback. They’ve been disappointed by their perception of results.

None of this is a failure. It is information that helps you to optimize the next thing that you try. You can read all the statistics that talk about how many businesses “fail” in the first year or two…those businesses didn’t fail. The founders decided to stop running them. Entrepreneurship is hard – it is not for everyone. But it is literally impossible to fail if it is something that you truly want – you just pick yourself up and dust yourself off after a setback and try again.

Transparently, I got so sick last year that I could barely work for four months. I had ~$10k a month in business expenses and was literally hemorrhaging money while I laid on the couch with debilitating bronchitis. I was scared. I didn’t know how to sell things when I could barely take a client call. As I watched my accounts drain, I seriously considered going back to grad school to finish a therapy degree so I could serve clients that way instead of continuing to build a platform for my work.

When I finally got better, I made a different choice – I invested $10,000 on a business credit card to build a course for all the things I wish I had known when I had started my business six years earlier. It was scary to take on that debt at that time, but I can tell you that less than 10 months later I am on track to out-earn myself for the sixth year in a row.

You can’t fail in business. You can only be presented with challenges that invite you to come up with a new approach. How do you cultivate safety in that? Well…you cultivate trust within yourself. Trust that you will have your own back. That you could always get another side hustle or temporary job. You’re a boss who has a lot of marketable skills and people would be lucky to work with you… and because of that, you are just as capable and well-resourced to figure out how to use those same skills to work for yourself.

If you’ve been waiting to start a business, the best time to take action was yesterday and the second best time is now. But your biggest asset will be your mindset, and you’re going to want to cultivate the most resilient and courageous one possible as you take the brave and valuable step of trying.

Literally just try. I promise what you learn will help you take the next step too. If you are looking for more helpful entrepreneur tips, you can learn more from me @carakovacscoaching or at

Hi friends šŸ’—Iā€™m teaching a free workshop next week for those curious and interested in learning more-