3 Game-Changing Ideas for Transitioning from Employee to Entrepreneur

3 Game-Changing Ideas for Transitioning from Employee to Entrepreneur

The day I scheduled my first business meeting as a freelance writer, I showed up early like I would for any interview. I ordered my coffee, pulled out my laptop, and picked up my favorite pen.

And then I blanked.

Until now, every moment of my interviewing life had been as a subordinate. Please, dear HR director, see something special in me and offer me the position, or, Please, CEO, just take a look at these prospective deliverables and consider what a great asset I’d be to your company.

But now?

Now I wasn’t here to ask for a job. Now it was up to me to negotiate the terms of my business. And while I probably confused the kind woman who met with me for my first business meeting as CEO of Greesonbach Creative, I was taking notes in my head the entire time.

When you make the transition from employee to entrepreneur, you’re gearing up for a whole new conversation. And if you go into that conversation unprepared, it’s going to cost you. Here are three game-changing ideas that will help you make the transition more smoothly:

No more memorizing mission statements

This is not to say that you shouldn’t research your prospective client or business partner; you always want to know who you’re heading into business with, so do your due diligence (this may or may not involve LinkedIn stalking).

But whereas in a previous life you might have spent the morning memorizing some mysterious Board’s mission statement to show what a hireable go-getter you are, it’s more important to show up prepared with your own mission statement.

Who are you? What do you want? Why do you do what you do? These are the things that matter, and these are the things that will help you make real connections and get the business. Block out time to brainstorm your own mission statement so there’s never any doubt about what you want or where you’re headed.

Stop hiding

There are two secret shames of the side-hustler who wants to go full-time freelance. The first, and the first one that has to go, is the nagging sense that you’re not good enough to go full time. The second, more dangerous shame is the sense that you’re doing something wrong that’s going to get you in trouble.

When you work for someone else, you start to see your time as “purchased.” You start to feel owned, like your time is not yours to spend on what you like. If you’re developing your freelance services or starting a business on the side, it’s probably with a mixed feeling of guilt. In some cases, it can feel like you’re cheating on your employer or hiding something by being successful and hardworking in your off-time.

When you take your first leap into self-employment, it can be hard to escape the sense of guilt and shame that you shouldn’t be freelancing full time. Fight it! And most importantly, own it! You’re the breadwinner for the business of you. You’re putting time into a profitable and meaningful venture. And that’s nothing to hide from. (Click to tweet this idea.)

business of you

Your self-respect upgrade is imminent

When you meet with a business contact as a self-employed small business owner, the new conversation is no longer about what a hard worker you are, or how punctual you’ll be for all the 9-5 shifts you’ll be working. That stuff simply doesn’t matter anymore, because it’s a given when you run your own business.

Once you have let yourself come out of the self-employment closet, get ready for an onslaught of self-respect. The conversation now is What will I do with the talents I have and How will I make the most out of every day I have? What partnerships will benefit me, and Do I want to put my name on this work or product?

And do you know what that makes you? A badass.

Because showing up on time and meeting deadlines are the lowest minimums you know. As an entrepreneur, it’s over-deliver or die. It’s exceed expectations or sign up for unemployment. And while the stress might lead to a few sleepless nights, the real result of day-in and day-out awesomeness is a life of meaning and self-respect for all you’ve accomplished.

Have you made the leap from employee to self-employed? What was the most surprising thing you learned in the process?

Filed Under: Freelancing


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