How to Craft your Corporate Exit Strategy
As seen in Fast Company on 1/11/25
Tired of the Corporate Grind? This is How to Craft an Exit Strategy
As RTO threatens an end to flexible work arrangements, many workers are opting out of the traditional career ladder altogether and crafting an exit strategy.
BY CAT O'SHAUGHNESSY COFFRIN 5 MINUTE READ
There’s an important trend unfolding across the corporate sector, from mid-career professionals to the most experienced executives: we’re leaving. As return-to-office policies continue to increase and threaten an end to flexible work arrangements, many workers are opting out of the traditional career ladder altogether and crafting an exit strategy.
Rather than steadily climb toward reaching the C-suite and staying until retirement, corporate employees are choosing to rewrite the rules for career success. Gone are the days of one company or one job at a time, and in their place is a steady rise in portfolio careers,independent consulting, freelancer networks, and fractional executives.
It can be both enticing and intimidating to step outside the lines and reimagine your own trajectory in this way, but it is an extremely rewarding path to consider. So, if you’ve been contemplating a path outside of the traditional corporate journey, here is a road map for staging your own exit strategy.
STEP 1: EXPLORE THE IDEA
As with most new and scary concepts, you can get started by simply acknowledging the potential idea. Try writing and then speaking about your desires to your safest and most valued confidants:
Why do you want to exit?
What’s driving you?
What are you afraid of?
What does success look like?
If you have a coach or an advisor, work with them to itemize the biggest obstacles keeping you in place and discuss potential ways you can work through them. When I was planning my own corporate exit strategy in 2019, I spoke with my therapist about all the worst-case scenarios I had in my mind for each of my fears, and in the end, none of them was insurmountable.
Slowly, systematically, my “why stay?” list got much less compelling, and my “why not?” list became a very strong case for leaving.
STEP 2: RUN THE NUMBERS
The biggest obstacle for many of us, of course, is the income question. So, try facing this head-on to help you get real, rather quickly, about the tangible requirements to make this move.
In the independent consulting world, we call this “the rent equation.” How much income do you need each month to cover your baseline needs? How much to feel safe and comfortable? This won’t be your revenue forever, it’s just a starting point that can feel doable and accessible.
Companies keep employees in place through a complex web of compensation spread across salaries, benefits, bonuses, stock options, and other intangibles. Try to simplify the equation by building a list of your core expenses, and then think about how much you really need to earn to become free. Don’t forget your deductions will change when you’re self-employed—often for the better.
This is just a starting point. You’re trying to make a theoretical concept feel more real so you can build the case for yourself and turn a nebulous idea into something realistic.
STEP 3: DEFINE YOUR VALUE PROPOSITION
This is a big one that will require some deep thought. Carve out some time where you can reflect and think through your personal value proposition, defining what you have to offer, and to whom.
When you work for someone else, it’s easy to conflate your value with your title, your role, or even the function of your team. The objective in this case is to begin to separate out those elements from what you, as an individual, have to offer and who you are best suited—or most energized—to serve.
BY CAT O'SHAUGHNESSY COFFRIN5 MINUTE READ
There’s an important trend unfolding across the corporate sector, from mid-career professionals to the most experienced executives: we’re leaving. As return-to-office policies continue to increase and threaten an end to flexible work arrangements, many workers are opting out of the traditional career ladder altogether and crafting an exit strategy.
Rather than steadily climb toward reaching the C-suite and staying until retirement, corporate employees are choosing to rewrite the rules for career success. Gone are the days of one company or one job at a time, and in their place is a steady rise in portfolio careers,independent consulting, freelancer networks, and fractional executives.
It can be both enticing and intimidating to step outside the lines and reimagine your own trajectory in this way, but it is an extremely rewarding path to consider. So, if you’ve been contemplating a path outside of the traditional corporate journey, here is a road map for staging your own exit strategy.
STEP 1: EXPLORE THE IDEA
As with most new and scary concepts, you can get started by simply acknowledging the potential idea. Try writing and then speaking about your desires to your safest and most valued confidants:
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Why do you want to exit?
What’s driving you?
What are you afraid of?
What does success look like?
If you have a coach or an advisor, work with them to itemize the biggest obstacles keeping you in place and discuss potential ways you can work through them. When I was planning my own corporate exit strategy in 2019, I spoke with my therapist about all the worst-case scenarios I had in my mind for each of my fears, and in the end, none of them was insurmountable.
Slowly, systematically, my “why stay?” list got much less compelling, and my “why not?” list became a very strong case for leaving.
STEP 2: RUN THE NUMBERS
The biggest obstacle for many of us, of course, is the income question. So, try facing this head-on to help you get real, rather quickly, about the tangible requirements to make this move.
In the independent consulting world, we call this “the rent equation.” How much income do you need each month to cover your baseline needs? How much to feel safe and comfortable? This won’t be your revenue forever, it’s just a starting point that can feel doable and accessible.
Companies keep employees in place through a complex web of compensation spread across salaries, benefits, bonuses, stock options, and other intangibles. Try to simplify the equation by building a list of your core expenses, and then think about how much you really need to earn to become free. Don’t forget your deductions will change when you’re self-employed—often for the better.
This is just a starting point. You’re trying to make a theoretical concept feel more real so you can build the case for yourself and turn a nebulous idea into something realistic.
STEP 3: DEFINE YOUR VALUE PROPOSITION
This is a big one that will require some deep thought. Carve out some time where you can reflect and think through your personal value proposition, defining what you have to offer, and to whom.
When you work for someone else, it’s easy to conflate your value with your title, your role, or even the function of your team. The objective in this case is to begin to separate out those elements from what you, as an individual, have to offer and who you are best suited—or most energized—to serve.
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Whether you intend to seek out private board or fractional roles, build an advisory or consulting practice, or want to transition into coaching, you need to have a strong feel for what you can do and for whom. Write this down in the simplest, clearest way possible and use it in your outreach.
STEP 4: TAP THAT NETWORK
Now it’s time to lean on your network. You can’t expect anyone to help you make the leap if you don’t ask, and they won’t know how to help if you are not clear and direct in what you ask for.
Start with your strongest mentors and closest allies and let them know you’re considering striking out on your own. Weave in language from your value proposition and let them know what you are hoping to do, who you would like to work with, and your ask of them. Typically, you are asking that they be aware of your goals, keep you in mind, and let you know of anyone you ought to meet.
People tend to avoid this kind of outreach because they feel uncomfortable with the ask. But keep in mind that when you do the work to clarify your goals and needs, your champions will always be happy to hear from you and will appreciate knowing how best to help. Avoid group emails and write authentic, personalized notes that sound as if you’re chatting over coffee.
In this phase, don’t forget to grow and expand your network as well. The contacts that got you here probably aren’t the contacts that will help grow your new business endeavors. Make sure to identify others who have already left the corporate grind and ask for their wisdom, look up people in your desired space and follow and engage and interact with them. Infuse new ideas into your thinking.
STEP 5: SPEAK UP
People will not think of you unless you give them a reason, so visibility matters. Use platforms like LinkedIn and local events to show up, and write and share your thoughts wherever you can. Getting out of your echo chamber will help you feel less stuck and more connected to others who might end up becoming partners, advocates, or clients going forward.
This is hard. Many leaders feel wildly uncomfortable creating original content and sharing their expertise, but it is a powerful way to signal to those you know, and those you don’t yet know, that you’re available, experienced, and ready for business.
Most of all, don’t overthink it.
Get started. Send some signals, do some thinking and writing, and see what comes back. You may find that your first consulting or board opportunity is easier to pin down than expected—and suddenly you are on your way.
It’s easy to stay still, and far more rewarding to take the risk and carve your own path. The exit sign is this way, and you deserve to at see what’s just beyond that door.
You’ll never know if you don’t at least take a peek.
Check out the original piece here.