Successful Career Change Strategies for Senior Leaders

Are you considering quitting your job to do something completely new? According to an analysis by Pew Research Center, half of the employees who quit their jobs in 2021 made a career change. 

I’m a career coach, and in my new Audible Original series, How To Change Careers, I share my own journey of leaving a career in corporate America to become an author. I know from my own experience that it’s never too late to pursue a new path. The typical American employee will spend almost 100,000 hours at work during a lifetime. The work that we do matters.

If you’re a senior leader who is considering a major professional pivot, here are three steps you can take to set yourself up for success.

  • Map Out Your Financial Commitments and Income Needs
    It’s important to do the math and as you consider your next chapter. Clarifying how much you will earn in your new career is just the starting point. Take time to assess how your career change will impact your income by outlining a budget with provisional timeframes, such as 12 months, 18 months, and 24 months.

    If your earning capacity will be impacted during a transition, this will allow you to project your real-life expenses and determine how to budget for your career change. If you are likely to have a gap in earnings, diminished earnings, or if you need to invest in further education or training, make sure you have sufficient savings to give you a cushion.

    Your provisional budgets need to be realistic. This will enable you to determine how much financial risk you can absorb and make decisions that align with your preferred risk level. If you’re pursuing a new career that’s going to lower your income temporarily, or for a longer period, it’s important to know if this is a tradeoff that you can both embrace and sustain.

    Money is a common reason why we stay stuck in careers we don’t want.  As a career coach, the words “I hate my job, but I need the money” are something I’ve heard time and time again. Only you can decide what your non-negotiables are and how you value or consider the opportunities and challenges that lie ahead.

    It’s essential that you make assessments not just with your heart, but with your head and a calculator too, so you can problem solve potential pitfalls. If needed, work with a financial planner to get objective and expert advice on all the considerations so you’re making the best possible decisions for you.

  • Choose Your Career Change Strategy
    When it comes to changing career, there are three routes you can take  – a parallel track, a gradual shift, or an accelerated pivot.

    The first option is pursuing a parallel track. This is when you keep your existing career and pursue your new career in your spare time. Option two is gearing up for a gradual shift. This is when you look for opportunities to sidestep into your new career over time at your current company. The third choice is making an accelerated pivot. This is when you plan to leave your current career to start over in your new field.

    If you’re considering the parallel track option, this doesn’t necessarily mean you need to hold down two full-time jobs at once. It could be you have two part-time roles, or maybe you keep your current career while you explore your new target career in your spare time. However, on the flip side, there are career pursuits that are not compatible with holding down a job in a different field. If your career change falls into this category, you have two options to consider.  Making a gradual shift or an accelerated pivot.

    Many career transitions are gradual. A great way to move into a new career can be finding opportunities to gravitate towards that role within your current organization. As a career coach, I’ve supported scores of professionals who have changed careers within their companies and started new paths in accounting, human resources, marketing, operations and more.

    But it’s not always possible to sidestep into a new career in the place where you already work.  This is especially the case if you want to do something that is strikingly different. If you find yourself in this situation, you will need to prepare to make an accelerated pivot.

  • Be Prepared for the “What-If” Moments
    When you’ve crunched the numbers, earmarked the route to take, it’s not uncommon to wonder, “what will I do if it all goes wrong?”  If you find yourself ruminating over what-ifs, there’s an exercise that can help you visualize your future and adjust your actions.

    One of my favorite books is Do More Great Work by Michael Bungay Stanier.  Within it, the author shares an exercise called “What’s The Right Ending?” that asks you to identify three possible outcomes for a decision you’re contemplating.

    First, visualize an outcome where everything works out perfectly for you. Then, write that perfect story down in detail.  Next, write out a different story where this time everything goes completely wrong.

Finally, consider an outcome that’s not great and it’s not terrible, it’s just kind of in the middle, and write that “so-so” version.

The exercise is powerful because it uses a story telling approach that puts you at the heart of three potential outcomes – amazing, awful, and just okay. This allows you to visualize not just how your career change could progress, but also the potential opportunities and pitfalls. Your responses to each scenario will help you when it comes to creating contingency plans for your career change.  It will allow you to face your fears about the worst possible outcomes and give you space to explore just how amazing this next phase of your career could be.

When you have decades of experience under your belt in your current position, there is a lot to consider as you embark on your career transition. There will be practical and financial considerations coupled with a range of emotions as we navigate the end of a chapter and the start of a new one. In my own career transition, I learned to trust that I would figure out some things as I went along, and that it was perfectly fine to seek other people’s help when I needed it.

Remember, you’re in the driving seat for your career and you can decide what to pursue. You don’t have to put a ceiling on your own potential.

Written by Octavia Goredema.
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