The Psychology of Going from Employee to Business Owner - Christine Kane

We all love the storyline that goes like this: When you have your own business, you’ll be able to…

√ Live in your yoga pants.

√ Work out whenever you want.

√ Meet your smiling bubbly kids at the bus stop

√ Schedule your days around your afternoon hike with your dog

√ Run errands while the rest of the world is at work.

This is the fun part, right?  It’s freedom!


And…I’ll let you in on a secret that me and my Uplevel coaches are passionately serious about: (We’ve helped many clients cut the cord and leave their jobs.)

The true test of whether or not you’ll succeed at running a business is not how much you crave freedom.  That’s a given.  You’re an entrepreneur after all!

The true test of entrepreneurial success is in your mindset.  With freedom comes responsibility.  So when you leave your job, you have to re-wire your brain. 

Here are the psychological shifts our clients and students have found to be the most surprising parts of becoming full time entrepreneurs…

1 – When you were an employee, you had a boss.  

Now that you’re your own boss, you have to be the one to determine your strategy.  You have to be the one to set the schedule. You have to be the one to manage this unmanageable thing called YOU.  (I devote an entire week to this in my Uplevel Your Business Program!)

This might sound like no big deal – but it’s probably the hardest part of the entrepreneurial journey especially when someone realizes that she’s a much worse boss than any she’s ever had.  

One of my Uplevel Academy clients reaching out for "boss" advice!

One of my Uplevel Academy clients reaching out for “boss” advice!

2 – When you were an employee, you had deadlines.

In my Becoming360 Program, we focus for an entire week on what I call “Managing your Power.”  In other words, you are a powerhouse of energy, ideas, and creativity.

Understanding that means that you are going to have to find ways to pull it out of you without firehosing the world, your schedule, your timeline.

If you don’t learn how to do this, you’ll end up overwhelmed and you will splatter your energy constantly.

When you were an employee, your company probably knew this about you, and they were intelligent enough to break down everything into project-like deadlines, timelines, milestones and meetings.  Learning how to do this for yourself is another matter altogether.

3 – When you were an employee, you had to, you know, not wear pajamas to work.

I know. I know.  Your bathrobe rocks.

But the thing is, it’s possible to take this too far.

Dilbert - Clothing optional

There’s a psychology behind dressing up and looking the part that you play.  This doesn’t mean you have to put on a suit and tie or pantyhose.  But you may wake up one day and look in the mirror at your cat-hair covered yoga pants, unwashed hair and fuzzy slippers and wonder if, just maybe, the way you are treating yourself could be having an impact on how your business treats you.

4 – When you were an employee, you didn’t have to market.

A few years ago, I was in a day-long VIP session with a brand-new client.

We spent the morning mapping out a new program she wanted to create. We laid out the modules. We listed the worksheets, giving them compelling names.  We set the schedule and dates of the program.  She was super excited…all wild-eyed and dizzy with her new clarity.

Then I said, “Okay, so let’s make a plan for how you’re going to market this program.”

She glazed over.  Yes, she actually said, “Really?”

This happens to way too many entrepreneurs.  They were hoping they didn’t have to do this part.

Think about it.  You love the idea of offering something, right? You love the idea of making stuff, right?  “Creativity? Gimme some of dat!”

But marketing?  It’s like someone just totally harshed your buzz.

When you were an employee, you didn’t have to worry about the marketing.  I mean, even if you were in the marketing department, you didn’t really worry about it, did you?  Only your part of it.

When you own a business, you have to find people to buy the great things you do or make.  And if you’re like many newbie entrepreneurs, your definition of marketing is limited to your assumptions about marketing. Which usually conjure up images of manipulation and sleaze.

But marketing is the ultimate service. Without it, all you have is a roomful of products and ideas. And no one to buy them.  (I meet tons of would-be coaches and business owners who have basements full of books, binders and boxes they never sold.  Why? Because they didn’t market.)

So you’ll have to get clear. This means identifying your ideal client. It means owning the value you deliver.  It means understanding the results you offer.  AND – being able to communicate that clearly in all of your materials.  (If you’re on my list, you’ll be getting an email next week about a free webinar I’m hosting where I’ll be teaching these strategies! Keep an eye out!)

5 – When you were an employee, people cared about the letters after your name.

When you were an employee, your email signature contained a vast collection of letters after your name. All your degrees, certifications, and validation of your title, role and position.

Now that you’re a business owner, no one really cares about that.  They care about themselves. They care about the results they get from working with you.  This is communicated in your marketing.  (See #4.)

If you’re in love with all your letters, by all means use them.  But now your attention will shift to creating valuable offers and packages that turn prospects into clients.

6 – When you were an employee, you just walked in and did your thing.  Big picture, schmig picture.

As an entrepreneur you have to expand your brain to include not just the task at hand, the thing you want to do today, the idea you are off and running on…

…but the impact this idea has on your big picture…

…and what the big picture is at all.  Do you know?

New business owners often get caught up in working in their business – all the nitty gritty tasks –  and forget to work ON their business. Then they wake up one morning, and have no clients left, and no systems set up to get new clients.

7 – When you were an employee, you didn’t have to invest in you.  The company invested in you.

If you’ve been an employee, you may be used to saying things like, “I’ll go to that event when the company pays for it.”  Or “I’ll take that program if my boss foots the bill.”  “I’ll only do that if my insurance plan covers it.”

Being a business owner means you have to drop the mindset of “spending” money and own the mindset of “investing in your results.”  This means recognizing that you ARE the company. And the company must take care of you, because you are its biggest asset.

Going from employee to entrepreneur

One of my students describes what it feels like when you’ve made the shift from employee to entrepreneur!

Your mindset must shift into an investment mindset. if you don’t invest in your own growth, health, marketing, or scalability, your business will slowly die.  Duct-taping your solutions, putting it all together on the cheap, creating a DIY mastermind of local folks who know just about as much as you do about having a business – all of this may work for a time – but investing requires faith in your own growth.

Employees rarely have to make this kind of decision, a future-based decision.  It’s where your intention – this thing you say you want or dream of having – gets legs.  (Or gets stranded.)

Your turn.  What was or has been your biggest psychological shift of moving from employee to business owner?

  • Nicole Clark. LMSW

    This post is right on time! I’m resigning from my job on 5/31/16, and while I’m completely excited, #6 resonated with me the most. I definitely need to get review the systems I currently have in place to make sure they will truly work for me (I started my business over a year ago while working full-time.) I’m also working on really using my authentic voice to have a better connection with potential clients. I believe as I became busier with my 9-5, I was so drained that I did the bare minimum when marketing my services. I really need to have a heart-to-heart with my business. Thanks for writing this, Christine!

  • Patrice A Federspiel

    For me, working ON the business rather than IN the business is still the hardest part. It’s so much easier to work in the business, and when I’m feeling low or worn out, at least I know I’m getting something done. BUT it would be so much better if I took better care of myself and didn’t get “worn out” so I could work ON the business to improve my future.

    So perhaps, self-care is really the hardest part for me. Making the time to take better care of the “goose that lays the golden egg”.

    Thanks Christine for another great nudge foreward!
    Aloha, Patrice

  • Julie

    For me, there have been two major transformations. The first was being disciplined again. My company culture was not one of high performance, big ideas or accelerated decisions. I purposely dulled down my intellect, my pace and my passion to fit in. I didn’t realize just how much until I was on my own in business. Quite frankly, I had gotten lazy from spending seven years in an environment where I couldn’t exercise my energy. I needed to reignite my drive and passion. It took about six months, but now I’m back to my old self, cranking out really create work really quickly, accelerating my actions and decisions, and being disciplined with my time and energy – to include getting up early again and accomplishing more than I have in years.

    The second was getting back to the true me. That meant reconnecting with who I really am and shedding the persona of who I needed to be to fit in at the company. I’ve learned that I’m a chameleon who’s damn good at morphing myself to fit the situation or what I believe people want to see in me. I’m really good at persuading and convincing others with my communication. So good that they believe they know who I am and what I stand for. But I’m just playing the part or the devil’s advocate.

    Reconnecting with what I stand for, how I roll and speaking in my authentic voice has been the biggest growth opportunity by far. I realize that it’s important to be intentional and deliberate with my words, that they define me. And being me in the world is exactly who I need to be, in my life and business.

  • Lynne Watts

    Hardest thing hands down was learning to network and market in a personal way. I was great at sending out email blasts about my newest offering but learning to personalize it and offer my coaching to people in a way that resonated with them personally while developing a relationship has been the biggest eye opener. Great post!

    • Christine Kane

      Thanks Lynne! And yes, being fully IN (and really – you could say “intimate”) in your marketing is a huge part of success – and it’s so scary at first. But hey – look at you now, baby! 🙂