The Beauty of Calling the Shots: The Ups and Downs of Entrepreneurship 


The Beauty of Calling the Shots: The Ups and Downs of Entrepreneurship with Sal Cincotta

Being an entrepreneur is not for everyone. After 14 years of being a full-time working professional photographer, this is reality talking. For many of us, we love the comfort and security of knowing there will be a paycheck each and every week. Show up, do our jobs, and we will be paid. Don’t get me wrong, I come from that world. I worked in corporate America for 10+ years. I loved knowing that every two weeks, my bank account would be refreshed, but when it came to personal satisfaction, I was miserable.

After 14 years of doing this, I have experienced many ups and downs. Today, of course, I know I made the right decision, but 10 years ago, during the struggle, I wasn’t so sure. So, if you are considering quitting your job to pursue a full-time career in photography, here are some things to consider when you weigh the pros and cons.

Just know, I highly recommend it. There is nothing more challenging or rewarding.

Have a strong support network

You are not going to be able to do this alone. If you do not have a strong support network, you will fail or worse, you will be fighting an uphill battle the entire way. Ultimately, this will make the journey quite miserable for you. And there is nothing worse than working your ass off and feeling like you are all alone on this journey.

Early on, I thought I had all the support of friends and family, only to find out and realize that these people were not believers, they were just riding my coat tails. I have always said, there are two types of people in this world: those who will stay in the trenches with you when you need them most, and those who will hit you over the head with a shovel to get out and save themselves.

Sadly, early on, I was surrounded by the latter. Worst of all, I didn’t see it until it was too late.

Today, with lots of experience under my belt, I can smell this a mile away. I can tell you that you need to be ready to cut these people from your life and your business very quickly. Surround yourself with like-minded people. Now, be very careful with this piece of advice. I am not advocating surrounding yourself with an echo chamber that tells you that everything you do and say is pure genius.

Instead, surround yourself with people who share the same goals and objectives. People who will push you and challenge you to be better. People who will call you out on your bullshit, not to hurt you, but to make you and the team better. Today, I have honest people in my inner circle. And while yes, it can be exhausting as the owner of a company to have to debate every idea you have, I can tell you, the end result is usually spot on, and you’ll have more skin in the game from your team, who will stand with you in the trenches.

Save more than you think you need

I screwed this one up royally. When I first quit my corporate job, I really thought I had more than enough saved. Well, within three months, I realized I was about to be out of money, and bankruptcy would be close behind. Again, today, I am fortunate that day never came for me. However, this is a huge misstep for almost every entrepreneur.

My advice? Make sure you have at least six months of bills covered. Step back, and put a spreadsheet together of all your expenses. Make sure you have six months’ reserve in the bank. This ensure that even if you do nothing for half a year, you will not have the pressure of paying bills nagging at you. Why is this so important? Because you have to focus on one thing: growing the business and bringing in new revenue.

Now, if you are smart, you will start building your book of business way before you punch out of that corporate job you have. Spend time and energy on marketing and ensure your calendar is starting to fill up. In my opinion, I would recommend you have at least 30 to 60 days of shoots booked out. This is a sure sign that your marketing plan will work and that you know how to bring in business. The worst thing you could do is stash six months of money in the bank and then burn through that trying to figure out marketing. Use your time before quitting to get your marketing and business plan in order. This is crucial to your success.

Be confident in your vision

This is your business. Your company. Your future. You must be confident in your vision. You cannot build your company on someone else’s vision. Think about it. As a photographer, when clients come to me with their Pinterest vision boards, I typically hand them back. Why? Not because I am trying to be obnoxious, but because that was not my idea. I can’t execute on someone else’s vision any more than another photographer can execute on mine.

You are the CEO of your company. This is one of the tasks of all CEOs. Set the direction for the company. Your job is to set your creative vision for your brand and push that forward. If you need to adjust your vision, you will know when the time is right. What we can’t do is abandon or change that vision every time there is a little hiccup or someone on our team doesn’t agree with or understand it.

This is why you need a strong support network. Think of your network as a board of trustees. They should believe in you and your vision and support you in them. Allowing someone to alter your vision is a sign of no confidence to me. It means you don’t believe in your own vision and can’t see the path to success. And if you don’t believe in your vision, why should your team? Can you see how this quickly becomes cancer to your organization?

Block out the noise. Trust your instincts

Listen to me when I tell you this. Cut it out, paste it to a mirror, highlight it. The amount of people who told me “it couldn’t be done” would shock you. Instead of allowing that to instill doubt, I used it as fuel to fire up me and my team. To that point, there is no one on my team, at least not for long, who shares the belief it can’t be done. Why? Because these doubting toms must go! Their infectious thoughts will spread like wildfire through the organization and start creating fear and doubt within others.

Remember this: If it were easy, everyone would do it. That is more than just a saying. It is reality. How can anyone share your vision when most people are so small-minded that they can’t relate to your desire to work for yourself? “Why?” they will ask. Most are paralyzed by fear. Do you really believe they can share your big-vision dreams? Most can’t. And you need to block this out or it will distract you.

Noise comes from a lot of places. Your competitors. Your family. Your friends. It can be a distraction, without a doubt, but you must be focused and committed to your dreams. Many times, the doubt comes in a very veiled way. Most people are masking their own insecurities, using phrases like,  “We are just worried for you,” “I’m just asking questions,” etc., when what they really mean is, “Hey, I’m too chicken shit to do what you are doing.”

I would respect people more if they were more transparent, but they are not and never will be. Your competitors are the worst. They are so fearful of losing what they have that rather than competing with you, they will say stupid shit to get you off your game. I have experienced this repeatedly with my local St. Louis photographers, who take petty and childish shots at me by blocking me from local photography groups, spreading rumors with no facts or altered context, or just trolling us online. The funny thing is, none of this impacts my business. Instead, it just ensures they stay lost in this vicious cycle of hate and are completely distracted from achieving their own success because they are too obsessed with mine. When this starts happening to you, celebrate. It means you are doing something right.

Celebrate success

There was a three-year window where the business was growing so fast that we could not keep up. I’m not talking about 10-percent growth. The business was doubling and tripling in size, revenue, and scope. The one thing I wish we had done more of? Celebrate those victories more.

Take time to celebrate and enjoy the wins, no matter how large or small. Celebration doesn’t have to be a two-week cruise. It can be as simple as dinner with the team. It is so important to your mental health and that of your team to celebrate the wins. I have found that celebrating throughout the year based on real victories keeps the team’s minds in the right place. They learn the simple mindset of work hard, play hard.

The key to all this is defining success. What does success look like? Is it winning a big account? Is it hitting financial goals? During the year, we celebrate when we hit certain growth goals, and the team is always aware of those goals. This ensures we are all marching to the same beat.

When it comes to end of year, we celebrate baller style with a Christmas party that makes some weddings look tame. I love giving my employees a taste of the finer things in life. We fly in a chef, a sommelier, a pastry chef, and décor that is out of this world. We treat our team to an eight-course, wine-paired meal, overnight accommodations, and a morning brunch the next day. This is no cheap event, but the team understands that this event is tied to working their asses off all year.

Find a way to celebrate those victories, keep yourself and your team motivated, and keep crushing your goals! You got this.

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To read the full article, launch the digital version of the January 2020 magazine.

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