What to Expect When You Change Careers to Become an Entrepreneur

Leaving one job and starting another – even on our own accord – is listed as one of the top 5 most stressful experiences.

The others? Death of a loved one, divorce, moving, and major illness. I mean, these are often traumatic, life-changing events! And yet, most of us try to brush off our impending career change as something that’s no big deal. In fact, we should actually just suck it up and continue with our soul-crushing work because, really, isn’t that what adults do? 

When we know it’s unacceptable to spend the next insert-however-many-years-you-have-before-retirement-here years being drained and unfulfilled at best and abused at worst, it’s time to start initiating change.

Our cavewomen brains HATE it when things change, and double hate it when we’re the ones who are controlling it! It’s one thing to have to run from a bear that just so happened to stumble across your tent in the woods, but it’s another to call for the bear and ask it to come charging, amIright?!

To soothe our inner cavewoman and inflict a bit less trauma on ourselves, here’s what to expect when you change careers to become an entrepreneur:

  1. There will be a moment where you have to jump – no matter how prepared or confident you are – and it’ll be damn scary. I like to preach that quitting your job does not have to be a jump off a cliff. Instead, it could be you walking directly on top of a safety net, eventually noticing that you’re walking on your own and the net is a few feet behind you. But no matter how many safety net tasks you’ve crossed off, or how much money you have in your savings account—giving your notice will make you feel like peeing your pants on a rollercoaster. If it doesn’t? Be worried.

  2. You’ll yearn for support from like-minded people. Community. Community. Community. I hear it from the vast majority of my clients, regardless of whether they feel supported at home. You are probably going to want to seek out other entrepreneurs, locally and/or virtually, and have a hive you can go to for resources, recommendations, and help. Or you can just continue to lean on the likeminded women who launched alongside you (ahem ahem).

  3. You’ll be waiting for someone to walk in the door and take you back to your old job. I expected this for months when I quit my Executive Assistant job in 2010. I didn’t purge my closet of my business casual clothes for months because it didn’t quite feel real! People might ask if you feel like you’re on vacation, and it will, in a sense – a working one!

  4. You won’t make as much money for the first few months (or year!) that you did at your last job. I don’t care how long you side hustled for – it’s near impossible to match your salary right out of the gate (although I made it happen during my first calendar year, woot woot!). Lower your expectations and realize that you’re playing a long game here.

  5. You’ll pinch yourself that It actually happened and You’re really doing it. For years. It's been over a decade and change for me and I’m still shaking my head. HOW is it possible that I can be a successful business coach, calling the shots and doing work that lights.me.up?! And I can be making more money than I ever did at a “stable” job? Seriously pinch-worthy, even all these years later.

  6. You’ll gain trust and confidence no matter what the outcome is. Even if your business doesn’t work out, or if it winds up looking different than when you started, you will take away so.damn.much. One of my clients said that starting a business led to more growth and clarity within herself than anything else she’s ever done. Ain’t that the truth! Never underestimate the act of doing.

  7. You’ll have to be a beginner all over again. And seriously? It’s kind of the best. You’re likely in a head space to be totally open to experimentation without major repercussions and learning the process that works best for you. Plus, we all have more excitement and enthusiasm at the beginning of adventures with fewer expectations, making it easy to keep positive momentum cooking! 

  8. You’ll have to learn how you work best and then make the rules. This might be weird, especially for those of us who had never been in a managerial role before. Even if you’re working without any outside help, you’ll have to discover how you can best manage your time and projects, how you want to communicate to your clients, what your boundaries are. All I have to say is: Get comfortable with being uncomfortable!

  9. You’ll experience more work/life integration than you ever have before. A client of mine used that phrase and I love it: work/life integration. Working from myself took away the distinction I felt between my Executive Assistant “persona” and my wife/daughter/friend self. Now, I’m just me. 24/7.

    90 Day Business Launch will help make all of the above truths and realities for you, and I’ll be there to help you navigate it all. Let’s make this top 5 stressful experiences into one of your top 3 BEST experiences by working together! See you inside

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