July 13, 2021

How to Transition Well From Corporate Life to Running Your Own Business

How to Transition Well From Corporate Life to Running Your Own Business

Do you want to ditch your corporate career? In this episode, Kathryn Thompson shares how to transition well from corporate life to running your own business.

Are you scared to transition from your corporate career to full-time entrepreneurship? 

In today's episode, Kathryn Thompson shares how to transition well from corporate life to running your own business.

So if you’re attached to your corporate identity and scared to let it go, tune into this episode. 


  • The questions to ask yourself to start creating your transition plan out of corporate to full-time entrepreneurship.
  • Why the tips and tricks of one person might not work for another for quitting your corporate job.
  • How letting go of your corporate identity can be the hardest thing to do.

If this episode inspires you in some way, leave us a review on Apple Podcasts and let us know your biggest takeaway–whether it’s inspired you finally make the leap from corporate to full-time entrepreneurship or where to start making a transition plan.

And while you’re here, make sure to follow us on Instagram @creativelyowned for more daily inspiration on how to effortlessly attract the most aligned clients without having to spend hours marketing your business or chasing clients. Also, make sure to tag me in your stories @creativelyowned. 

To get your hands on how to write content that connects, and attracts the most aligned clients, grab it here!! 



I am super stoked to have you here today, tuning in, as I answer one of the most commonly asked questions that I get that isn't in relation to messaging, or copywriting, or launching and scaling your business basically. But it's how to transition out of corporate life into running your own business. 

As I reflect, evolve and expand my knowledge and experience, my response shifts, and it's changed even over the last five years since quitting my corporate job. It's why I never want you to hang on to every single word I say as gospel, because like any coach or mentor in the entrepreneurship space or somebody you look up to, they're just like you. They are living this imperfect life navigating this universe learning, changing and growing all the time. 

So what was true for me five years ago while I was quitting my corporate job, isn't true for me anymore. I've had a lot of time to contemplate, and really reflect on where things have gone and how my life has changed since quitting my corporate job, and letting go of that corporate identity. 

So your entrepreneurship mentors or gurus or the people you look up to, are really the same. They're evolving and changing. And so what was true for them, a year ago or two is likely not true anymore. So we've got to give people the grace and the patience and the openness to really allow them to evolve as you evolve as well in this entrepreneurship journey. 

We also sold our brick and mortar in August of 2020. So lots has changed for me over the last year, which is true for a lot of people, especially with COVID. It really shook things up, it changed the way people do corporate work or had them questioning if they enjoy their corporate work anymore. So as I look back over the last five years, I can say with some certainty, that I do have a clearer idea now right now in this moment, and what I would have done differently, but also what I think I did pretty well as I transitioned out of corporate, which was a 15 year journey. 

For me, I had developed a corporate identity. Craig and I, we don't have kids. So it was like a big part of who I was, and I was wrapped up in this corporate identity very much. 've always been pretty good at moving on and closing one door and reinventing myself but trust me, there's lots of things going on inside that might not necessarily be reflected, as I'm making these pivots. And for me, this transition from corporate to full-time entrepreneurship was so different from a lot of the other things that I did in my life. 

This was a little bit of a different transition than I think it was because I had spent so much time in corporate. So my hope for you from this episode is to share my stories in hopes that it really does help you transition out a corporate well, or pivot in your life or business, maybe turn that side hustle into a full time gig, whatever that might be. But like most things I share, I don't have this cookie cutter one size fits all approach to the best way I transitioned out of corporate or to assure you that you know, the way that I did, it was like the best way to do it. 

But what I can share with you is what I would have done differently now reflecting back on my transition out of corporate to full-time entrepreneurship. What worked for me or what I think worked for me at the time. 

Now, I’ll share what I wish I knew before I made the leap from corporate to full-time entrepreneurship and solid advice people gave me that helped make the transition easier.

I know there's lots of people that are out there that say leap from corporate, and the net will appear. While I understand the analogy, I feel like it's a bit misleading. So everything that I offer is hopefully giving you a perspective, from all angles and really painting a picture of what it’s like to make that transition from corporate or at least things to consider when going into full-time entrepreneurship. 

So the first question you need to ask yourself, is your decision to leave corporate from an aligned place? Or...are you doing it as a quick fix and escape from your current reality or circumstances? 

If you're somebody that wants to leave corporate for entrepreneurship, because you hate corporate, what makes you think you’ll like entrepreneurship? 

Maybe you’re like me and believe this, I’ll be able to ditch my corporate career and then figure things out as I go. Let me spare you the heartache.  That decision included four years of a lot of frustration, a lot of resentment, a lot of not living in alignment. And what that looks like is massive weight gain, and unhappiness. 

Another thing to consider is your tolerance for risk. I'll always say there's no real certainty in life and or business. Whether you’re working in corporate or an entrepreneur. Nothing is guaranteed for certain. But some people need more planning, some people need more certainty and what it's going to look like to make sure. So if you're like me and figure things out as you go, you'll probably resonate a little bit more with my story of what I would have done differently, versus somebody who really wants to plan things out and make sure they've dotted all the i's and crossed their T's before leaving corporate. 

And that's cool, too, then I would really suggest being in alignment when you make the decisions. And if you can, at any point, talk to as many entrepreneurs in the entrepreneurship space and in your industry about what it's really like. And if you can, and you're opening a brick and mortar, you could go work for somebody else, or job shadow and see what it's like. 

Because I think had I done that I probably would have been like, this isn't for me, or I don't really want to do this, or I'm getting a better sense of that. I visited a store for the first time after the contract was signed, and realized what it fully entailed.

Now in saying that, you have every possibility in front of you to pivot and reinvent yourself, I did that we sold our brick and mortar. So even though you make the decision right now, in the moment doesn't mean you have to stick to it forever. And that's another big sort of learning. For me, when we signed this deal, it was like, okay, this is a big commitment to leave my corporate career and do this. But there is always space to pivot.

Now, in terms of transitioning from corporate to something that is in alignment with what you want to do, and you're so passionate about that thing, then my input is one of the things that I know I did really well when leaving corporate was to ensure that I had a safety net in terms of money or cash flow for me to live off of in the initial stages of the business so that if we weren't making money or money wasn't coming in that I didn't feel the pressure to make money. And everyone’s situation is different here with what expenses they have in their life, so it’s totally out of integrity for people to say they should just leap from corporate to full-time entrepreneurship.

The other big one, making sure you have a clear picture of what your operating costs are and what you need to sell in order to cover those costs. Sometimes we get excited with entrepreneurship and what we think it entails that we forget to replace our corporate salary. We must sell a specific amount not including the costs to run the business. It’s when you have this clear picture that you can go in knowing exactly what you need to make.

Another big thing I learned after quitting my current job is how to make the business sustainable. There is a difference between profitable and sustainable. And I don’t think we considered this when opening our brick and mortar. Are you putting in place systems, processes that can scale without you? Or are you like me, and didn’t think of that which caused us to work way harder than we needed too.

Hopefully that’s given you some food for thought when it comes to how to transition well from corporate to entrepreneurship!