Ready for a Re-Do? Five Tips to Reinvent Your Career

Ready for a Re-Do? Five tips to reinvent your career at any stage of life…

By Holly Caplan

I recently made the choice to quit my corporate job. After putting up with the same negativity and toxic work environment for years, I decided it was time to go. I could feel this coming for weeks, and I had mentally prepared myself with the departure conversation.  When I made the exit it was on my terms and based on my principles.  I finally felt I was in charge of my destiny. I basked in this moment for oh about, four days. And then arrived the holy crap moment of – what now? I realized I wasn’t sure of what I actually wanted to do next. Being free from that job was what I had been waiting for, but that was now topped with a big red bow called fear.  Despite my outward courage and good intentions, I was terrified at the core. I knew I could survive financially for a while, but didn’t want to sit still at the same time.  I had to take a deep breath – several actually – and try and enjoy the fact I now had the space to evaluate what was going to fulfill me personally and professionally.

In this self -reflection period I realized I could take this time to reinvent myself.

I had known I wanted to reinvent myself for some time – the thought of leaving corporate America and doing my own thing felt like a dream for years.  I had this conversation with friends and colleagues over lunch or cocktails, kind of fantasizing about the what-ifs, but now I really had the opportunity.

If you are in this position now, or know you will be in the near future, take a deep breath, and consider the gift of freedom, but remove the big red bow of fear.  You can find a path that is right for you, it will just take time and effort. Here are five tips to help you along as you reinvent yourself:

1. Skillset Transfer:

Consider your history and think about what are you good at?  Maybe it is accounting or sales, but know what your niche is and at what skill you are the most confident. Stick with that skill and your transition to renewal will provide confidence and give you a foundation. Steve Adams, an Austin, TX based insurance franchise owner realized his abilities were best used when it came to customer service. “ During my previous career in big corporate America, I was great at building and keeping relationships.  I knew that these skills would transfer when I was ready to open my own business, and it is has worked well for me.”  Adams found that focusing on his strengths led him to finding a business where he found fulfillment and personal growth.

2. Focus on our core:

Although your years may have been spent in marketing, has it been satisfying?  Meaning, did you love the actual task of being a marketer, or perhaps it was the ability to tap into your creative senses that brought gratification. The point is here is to connect with what inspires you at the core of your being.  Mary Griffitts, an attorney from Dallas, TX has owned her jury consulting business for 15 years.  Along the way she realized a passion for screenwriting, producing and acting.  It meant enough to her to write a screenplay, audition for roles, and start her own production company – all the while keeping her day job. Her creative core has led her to this second career. Her advice to others is, “Follow your intuition, do what you love, and you will make your heart sing.”

3. Realize your priorities:

Make a list to identify what your top priorities are in the next phase of your life.  Write down what you really want. Is it having a certain job? Is it having financial stability? Is it having more time with your family? This will help you vet what is really important to you. From here you can shape the center of your reinvention plans around your wants and needs.  Stan Dietz, a Portland, OR based marketing executive said that he made this list and it has helped him create certain financial, career and family goals for himself. Dietz said he then took it a step further, “ I asked myself several questions. As I look at the larger question of  – what do I want to do? The answer is in general terms of the impact I want to achieve:  I want to have a positive impact on others around me. I also want to continue to be successful.  Success in this case relates to my cornerstone of the ability to take care of my family.” Not only was his process revealing, but he was also able to generate new ideas and interests.

4. Practice patience with yourself:

This is the hard part. Learning to have patience with you.  If you don’t have the answers to your big questions immediately, sit with it.  This did not occur to me initially, as I am one impatient person.  A long time friend of mine had to bring it to my attention. Her words were, “Be patient with yourself.” She was right. By practicing patience I took immense pressure off myself. Having patience also freed up my mind and more ideas  surfaced as a result.

5. Be list-less:

Don’t rely on your “list”.  What is a list you may ask? All too often we portray ourselves to one another as a list. We list our accomplishments, degrees, employers, and a bunch of other bullshit jargon that people tune out. We think this act of “listing” will help others understand who we are and validate our existence. Newsflash, no one gives a shit. Everyone has a list. Let go of the list, especially while reinventing yourself. This will get you closer to renewal and realizing your true definition.  It’s not that you were an executive of a company for 12 years, and were promoted to VP, it is that you led people and helped them achieve their goals – that is your specialty.  How you impact others is what really defines you and is how you make your mark. Explore this thought for your reinvention and you will thrive.

Look, reinvention is scary. It is uncomfortable and is full of the unknown. We all want answers to our big questions and to quell any uncertainty immediately. Take some space, be thoughtful and patient with yourself. Remember that this is a process and appreciate this time of exploration.

Holly Caplan is a workplace issues expert, career coach and author of Surviving the Dick Clique: A Girl’s Guide to Surviving the Male Dominated Corporate World. For more information, please visit, and connect with her on Twitter, @hollymcaplan.