The Secret Psychology of Moving from Employee to Entrepreneur - 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

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

√ Take 3-week vacations on tiny islands that serve drinks with little umbrellas in them.

This is the fun part, right?  It’s our (somewhat inflated) idea of freedom.


And…I’ll let you in on a secret that me and my Uplevel coaches are passionate about…

(HINT: We’ve helped hundreds of 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.  Which means that when you leave your job, you may have to re-wire your brain. 

Here are the most challenging psychological shifts our clients must make as they leave jobs and turn into 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!

An Uplevel Academy client discovers the pressures of being her own boss!

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

In my work with clients, I call this part “Managing your Power.”  In other words, you’re a force-field of energy, ideas, and creativity.

This means that you are going to have to find ways to access your power without fire-hosing your brain, your schedule, your timeline or your clients.

If you don’t learn how to do this, you’ll end up splattered and overwhelmed.

When you were an employee, your company probably knew this about you, so they broke down projects into 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.  This doesn’t mean you have to wear 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.

Years ago, I was in a day-long VIP session with a new client.

We spent the morning mapping out a program she wanted to create. We laid out the modules. We listed the worksheets, and gave them cool names.  We set the schedule and dates of the program.  She was 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.  She actually said, “Really?”

This is an all-too-common response.  The entrepreneur who hopes she didn’t have to do this part.

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.  You have to market.

And if you’re like many newbies, your definition of marketing is based on your assumptions about marketing: 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 benefit from 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.)

Start with clarity.

Identify your ideal client. Own the value you deliver.  Know the results you offer.  AND –communicate that clearly in all of your materials.  

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

In the old days, 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 cares.  They care about themselves. They care about the results they get from working with you.  This is communicated in your marketing.  (See #4.)  

Now instead of running out to get yet another certification, you must create valuable offers and packages that turn prospects into clients.  Hello value and positioning. Goodbye letters.

6 – When you were an employee, you just walked in and did your thing.  Strategy, schmategy.

As an entrepreneur you have to expand your brain to include not just the task at hand, the thing you want to do today…

…but the impact this idea has on your strategy…

…and what the strategy is at all.  

Do you even know?

New business owners 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 clients experiences the shift from paycheck to being invested in!

Your mindset must shift into an investment mindset. If you don’t invest in your own expansion, health, and marketing, your business will slowly die.  Duct-taping 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.  It’s called a “future-based decision.”  It’s where your intention – this thing you say you want or dream of having – gets REAL.  And it can be scary.  But it’s crucial for your growth.


Am I missing anything here?  What was or has been your biggest psychological shift of moving from employee to business owner?

  • Michelle

    Okay, this was exactly what I needed to read today. Thank you for always being “witchy” that way. 😉

  • Laura Rothenburg

    Thank you Cristine for this post
    I have to admit I am a technology refused saying that what I mean is my forte is not on the technology side, by being in my own business I have learnt so many things as being a one man band has been hard but also exhilarating. Keeping myself motivated to achieve all the business requires is not the problem but and I say but ‘THE MARKETING’ now that’s an enormous task, one I would like someone else to take care of. However, winning clients to take my classes has not been easy and a website yet to be finished is another matter.
    So this summer I am setting up a kids summer camp in the creative arts but have recruited some teachers into help which gives a sense of a team. This is what I miss most when I was working. The team work, working to an ultimate goal. So really for me I would like to build a permanent team very soon. The other thing is being self relient on creating the cashflow and keeping the big picture as the goal, visualisation is great and sheer determination is my path.

  • Robin Barr

    Love this, CK!! You “hit the nail on the head”, as always 😊

  • Amy Kay Watson

    Being an employee is such a great place to hide out away from the inner critic. If I felt unsafe, I could just pull back into my office, close the door, and futz around with a spreadsheet or a word document. Safe, safe, safe!

    Damn, I miss that some days.

    Now when I feel unsafe, I have to confront myself. I have to do my work. I have to sit down with my inner critic and hear her out, engage her in conversation, thank her for her input and then send her on a coffee break while I listen to other parts of myself for awhile. I have to be intentional about giving voice to those other parts so I won’t crumble in on myself. If I don’t take the time and do that work, my list of projects and tasks becomes a treacherous forest that I’ll do ANYTHING to avoid.

    Doing the work means I’m continually growing. Having a job meant I could let that slide for a few days, weeks, months, and even years.

  • Lucie Bland

    A lot of the content in this blog post resonated with me on different levels. First, I’m doing a lot of work to change my money mindset to invest in myself and my future results. I’m an Enneagram 1, have been a student for 7 years and then worked in the field of wildlife conservation, so spent years being a tight ass. Now I am changing my mindset by investing in my learning through UpLevel Cafe and using my business to fuel my career retraining, as my current employer does not do professional development. I also really enjoyed the piece about marketing being a service. I love serving people and I’m excited to connect with them over my offers, so that mindset makes marketing feels less sleazy.

  • 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! 🙂