Some things to think about when making the leap from employee to entrepreneur

by Jeff Hilimire on June 3, 2014

While I never considered myself an “employee” while at Engauge (I sold my first company, Spunlogic, to Engauge in 2008 and was there until 2013 as President and a board member), I certainly didn’t feel like an entrepreneur. When I started Dragon Army last September, I felt like I had been re-awakened as I was finally an entrepreneur once again.

Lately I’ve been thinking about the transition to being an entrepreneur when you’ve previously been an employee. Some things to consider:

Be ready to embrace change. If you’ve started a company, you’re going to go through lots of changes. If you’re not ready and excited about the change, you’re probably not ready to be an entrepreneur.

Say good-bye to process. At least at the beginning. When you’re at an established company, there’s usually a process, a “way things are done around here”. That’s not always a good thing – in fact, it rarely is – but there is piece of mind with knowing where to plug in and how to contribute. Not always the case with a new company.

Get ready to redefine your concept of commitment. When you have a job, your commitment is only as long as it would take you to get another job. If you get upset with the leadership, bang, you’re outta there. But if you start a company you need to be ready to stick it out through the toughest of times. With a new company, its all about the runway, and if you can’t commit to being able to stick it out for the long haul, then think twice about leaving the security of working for someone else.

Understand your new job is: EVERYTHING. At a “job”, you have a limited amount of responsibility. When you start a company, you (and your partners) are responsible for everything. Payroll. Sales. HR. Furniture. WIFI. Marketing. Product. Testing…Did I mention payroll? :)

You’ll need to find time to “think”. I still struggle with this one, but when you’ve started a company you’ll need all sorts of time to think and reflect on the journey along the way. And on that note…

Your calendar becomes uber important. Your time is extremely valuable when you start a business. You’ll be pulled in a million different directions and time management (and delegation when possible) is the key. I’ve been focusing a lot lately on managing my time better.

But the biggest shift will be the amount of RESPONSIBILITY you’ll be taking on. For some people, the immense pressure of running a business is overwhelming. Everything rests on your shoulders. You’re expected to figure it out, make the right decisions, lead the team through the storm, inspire them, make the tough calls…things you’re not usually expected to do as an employee. I was lucky that I cut my teeth on entrepreneurship as a young man and grew into feeling good with that kind of pressure.

What’d I miss?

  • Joe Koufman

    I would add that you have to find ways to make it fun for you and your team. Nobody wants to come to work every day in an environment where they can’t enjoy themselves. We as the leader of our organization are responsible for setting the tone to balance hard work and fun.

  • Josh Ludin

    Love your point that your new job is everything. At my business, I go from President to Janitor frequently.

    Josh Ludin

  • Jeff Hilimire

    Yup, you got it.

  • Pingback: New Lessons as a Start Up CEO()

Previous post:

Next post: