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Special Olympics Oregon with Ryan Avery

When is the right time to leave a company to start your own?

By Leadership, Motivation No Comments

One year ago today, I stopped working for an organization that inspired me. Everyday I went to work, I was excited by the mission, the people I worked with and my roles and responsibilities to help improve the lives of those we served. I had potential in the organization and the proposition of leaving to start working for myself was a difficult one to make.

Allison E with Special Olympics OregonI decided to leave my job at Special Olympics Oregon to become a full time speaker for three reasons:

1) I asked myself, “One day, when my kids ask me if I went for my dreams, I want to make sure I can tell them ‘yes’ with all honesty.”

2) Worst case scenario, I can always get a job again

3) As long as Chelsea was on board, I would be all in!

The decision was rational, frightening and exciting all balled into one. I felt like a peppy puppy having to choose between a run on the beach or a playdate in the park! How do you leave a job you love to create a company you know nothing about?

Here are six questions to consider if you are looking to start your own company:

AveryToday's First Office

This was AveryToday, Inc. “Headquarters” when we started last year. Dream BIG right?

Are you ok with taking a step backwards financially?

We planned for me leaving but we had to save more, spend less on things that are considered “fun” and use our finances to start a business. We even moved from Oregon to Texas to move in with my parents to save money on rent, you get better tax benefits when you own a Texas corporation and my mom and dad were willing to help support us emotionally throughout our transition.

I am not saying you will go backwards when you start your own company, but are you willing to if needed and invest your money into growing you company rather than living the lifestyle you already have? Are you willing to go three steps back to go five steps forward in the future?

Are you ok with working harder than you ever have?

When you start a company, there is a lot to learn. At the beginning stages of our company there were no weekends. We woke up early, went to bed late and replayed that schedule over and over again until I lost what day of the week it was.

Today, is a little different. I have a schedule, I take personal time and I still work harder than ever but those beginning months can be brutal if you are not prepared for your business to survive. It takes every ounce of energy you have.

Are you ok with things rapidly changing?
In this past year I have quit my full time job, moved from Portland to Houston, wrote a book, put on a 50-city North American Tour, planned a book tour and a world record, delivered keynotes, workshops and private coaching to leaders all over the world, I moved back to Portland, and now I am scuba certified. When you start your own company, things seem to always be changing. You do things you have never done. Are you ok with this?

Ryan Avery leaving Special Olympics OregonAre you ready to be your own boss?
This is the biggest thing you need to think about… Are you self-dicipled enough to make your company survive? Stop here. Think about this and come back to read the rest. Seriosuly think about what you are going to do to be self-dicplined because no longer is anyone telling you what to do, when to do it and how it should get done. It is 100% up to you. This is both freeing and very difficult to manage.

Do you already have a base and slight proof you can make it on your own if you try?
We didn’t start our  business by chance. It was our choice to leave but we planned, outlined how much money we were making, how much we could be making if we took it full-time. Planning doesn’t always work. Those first six months were brutal. We didn’t meet any of our financial goals for the first six months but we kept pushing ourselves and used the proof we had to remind each other  we could keep doing what we were doing. If you can do it once, you can repeat it twice!

Is your family okay with taking the leap with you?

Your family depends on you, they have to be okay with the above as well because this is not a decision you make alone, it is one y’all (yes I am from Texas) must make. Have a conversation with your family, tell them what you want to do. Ask them what they need and are how they are willing to help or support you on your dreams.

I went from employee to entrepreneur in 24-hours and today I own two successful business. I have a long way to go, more to learn and a whole lot more people to serve but I am ultimately glad I took the leap. You only live once, right? Take the above decisions to consider owning your own business. As scary as it was, looking back on this year, I made the right choice. You are not too young or too old to start, but what you must do is make a decision, start planning for the life you want to live and go for it!

As always…
Dream BIG,