What To Know When Transitioning From Corporate to Entrepreneurship

By Cindy Constable 

For leaders who have had a long corporate career, taking the leap into entrepreneurship can be exciting and confusing. 

The financial security and freedom of entrepreneurship can be appealing for women business leaders. Each of us craves the ability to be in control of our life and what we do. For leaders who have had a long corporate career, leaping into entrepreneurship can be exciting and confusing. 

I remember how scary it was to put in my two-week notice at a job I had worked for ten years. I was the CFO of the City of Ocala, Florida, and had reached the pinnacle of corporate success. I had a corner office, lots of staff and managed an eight hundred-million-dollar budget for the city. Leaving a job that the outside world considered incredible for entrepreneurship was one of the most complex decisions I’ve made.

Then came the realities of entrepreneurship. The transition from corporate to where my business is today was not easy. I can tell you firsthand that there are things you should understand before you make the leap into entrepreneurship from a corporate career. Here’s what women leaders should understand and strategies they can use to start and build their business. 

1. Be clear about what type of business aligns with your long-term life goals. 

When you’re starting a business, you naturally begin to research what works for growth and how you can accelerate the process. The internet and social media offer the opportunity to see entrepreneurship in action. There’s no shortage of articles, videos and podcasts about starting and growing a business.

It’s essential to consume this information with a filter as the advice can sometimes be given from a place of wanting you to invest in a product or service from the person providing the information. If you get pulled in through good marketing, you could waste months or years pursuing business growth strategies that don’t work or aren’t suitable for you. 

As someone newer to entrepreneurship — and someone in a corporate environment — you’ll need to know what makes sense for you. For example, you could offer to coach clients through your knowledge and experience around a topic. But, do you want to coach clients? Does coaching fit your personality and how you want to spend your time?

You could generate revenue through offering coaching, selling courses, creating products, offering fulfillment services, and several other ways. You’ll need clarity on how you want to spend your days and what model makes sense (for you) to build a successful business that brings freedom into your life. 

Don’t get caught in the trap of pursuing what seems to be working for other entrepreneurs. Find the business model and structure that works for you, and go deep in building a business with those elements.

2. Be strategic about how you invest and where you seek accountability.

Investing in yourself and your business is a great way to accelerate growth and foster self-care. There are areas in life and business in which you’ll need more help. However, discernment is required to make the best strategic investments. 

You’re probably inundated with marketing from entrepreneurs offering courses, coaching and services promising to help you get more clients and grow your business. Unfortunately, good marketing can sell bad products. More than that, women leaders transitioning from corporate should understand that you can’t spend your way into a successful business. 

Before investing in your growth, have clarity and do research. Know what training or services you’ll need to reach your next level of development. For example, you know that you need to post content on social media, but your time is pulled in too many directions. At that point, you might consider hiring a virtual assistant or a content creation agency. 

In addition to investing in products and services, be intentional about the company you keep. There are a lot of empowering networks that women leaders can join. Again, do your research and see which one aligns with you and your goals. Accountability is fantastic and can motivate you to take consistent action if it’s the right vibe for you. 

3. Make yourself and what you want to accomplish a priority. 

As a women leader, you’re pulled in a lot of directions. You may be a wife, mother, friend and support system for so many in your life. You can give away too much of yourself if you’re not careful and do not have enough left to work on the things you want to accomplish. 

You have goals, dreams and aspirations — they are important and should be treated as such. Every women leader should understand one significant thing: You have to prioritize yourself and what you want to accomplish. 

Take better care of yourself. There is nothing wrong with your ambition for what you want for yourself. You’re not a bad person for setting boundaries and prioritizing your goals. We need to break the societal conditioning that tells women leaders they have to be martyrs — that’s not the path to creating a life of freedom.


  • Incorporating self-care and fun into your business-building journey. 
  • Saying “no” more often and setting healthy boundaries.
  • Having plenty of “you” time. 
  • Letting go of what doesn’t serve you. 

It’s an interesting transition from corporate into entrepreneurship, but the possibilities are exciting. If you’re going to leap, understand these three things. You can build an amazing life and business with a strategic and clear plan. 


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