What I Wish I Knew Starting Out

The typical icebreaker: what do you do? I answer, “I own a PR and marketing firm.” This is often followed by, “How did you start your own company?”

A lot of people are intrigued by entrepreneurship. Many want to start their own companies, but they don’t know where to begin. I was in this boat. I focused on building my expertise, my network and my bank account, and I looked for an open door or a sign that would tell me: now is the time. Though I was eager to get going, I heeded the advice of smart business people and held off on making the leap for longer than I wanted to.

Then one day, it hit me like a ton of bricks. It was a Saturday afternoon and the company I was working for had just relocated offices. I wanted to get in over the weekend to get everything settled before a busy week. When I walked in and looked at my desk, it didn’t just feel new, it felt strange and unfamiliar. It was like there was writing on the wall: you don’t belong here. GO. Apparently, this type of experience is not uncommon among entrepreneurs.

Regardless, I spent the day convincing myself that I liked the new space and it was going to be a great place to work. However, the next morning, I woke up abruptly and I felt shaken, but I also felt unbelievably excited. I had so much clarity. It was time. Later that day, I filed for my LLC and the ball was in motion.

Many of you have already had your lightbulb moment, but I know there are still many others who want to start a business and haven’t found the right opportunity. Whether you’ve already hung your shingle or you’re still thinking about it, here are some things I wish I knew when starting out.

It doesn’t have to be perfect from the start

When I started (before partnering with Alyssa), the team consisted of me, myself and I. Having come from a larger firm, I put immense pressure on myself to deliver the types of results I was used to delivering with a multi-person team. I was doing that, plus trying to market my firm – building the website, managing social media, attending events, attending new business pitches and creating proposals. All of this meant putting in nights and weekends for significantly reduced pay. It’s what I thought I had to do to get off the ground. Instead, I faced major burnout!

While I wouldn’t trade the experience, I would go back and tell myself: work hard enough, but prioritize what you have to do over what you want to do. Deliver amazing results for clients and business growth will follow. With that growth, you’ll build capacity and the ability to evolve. But remember, every evolution and growth spurt brings its own set of obstacles. And that’s what entrepreneurship is really about: rising to the next challenge.

You have to make your own mistakes (and they will be frequent)

As an entrepreneur in Chicago, I’m lucky to have a great support system of so many others in the city. I am doubly lucky because I come from a family of entrepreneurs. I have so many people to strategize with and glean insights from.

But, I’ve learned even with access to great minds and knowledge, in most cases, Alyssa and I have to make our own mistakes. When they happen, we’re always hard on ourselves, but we make an effort to reflect and learn. Mistakes are about the only thing in business that are constant – the day we stop making them is the day we stop improving.

There’s never a right time

I think this saying is true for many things in life, but it’s particularly true of starting a business. I had my grand epiphany and quit my job to start Prosper one month before my wedding. There’s always a reason to put it off. If it wasn’t the big day, it would have been “wait until the New Year,” “Don’t start in summer, business is naturally slow,” etc. Know, there will always be people to discourage you and to give you reasons why you shouldn’t do it. It’s truly a choice only you can make. You just have to have the courage.

Looking back, was it the right time? I think it was just fine. I was able to bring in several clients straight out of the gate. I delayed my honeymoon by a few months, but by the time it came around, I was in need of a break anyway.

So what are you waiting for?