How to survive the first 90 days of a career change

How to survive the first 90 days of a career change

The hard work is done. You’ve tendered your resignation without burning bridges. You’re at peace with the sunk cost of putting a successful career trajectory on hold. You’ve modeled out your cash flows. Your health insurance is buttoned up. After all, quitting should be easier for executives – with savings come safety nets. Yet, once they quit they look more like deer in headlights than wolves of Wall Street. I should know, three years ago I was one of them.

I’m intentionally using “execs” quite liberally. One would qualify if a) you have savings for some kind of break and b) parts of your identity are tied to your industry or skill set. And even if the corner office feels like it’s miles away, do not despair; starting a contemplation practice, the power of life coaching, and loss-of-identity-induced FOMO are relevant at any stage of a career.

But first, a warning

You’ve presumably read Sapiens and are hip to the fact that humans crave stories. In the book, Yuval Harari argues that it’s stories that separate us from the rest of the animal kingdom. Examples of these “stories” include religion, currency, law, and political ideologies. These “stories” enable mass coordination across mankind, resulting in our spectacular leap as a species.

Ok, but what how does this tie to resigning executives? Well it turns out that “the career” is a very powerful story. But just like fish are blissfully unaware that they swim in water, most humans are blind to power these stories have over our lives.

In his epic 90 minute read on finding a career that fits you, Tim Urban distills these stories into a metaphorical octopus, capturing the “career” is a mash up of our personal, social, moral, lifestyle, and pragmatic needs and desires.

From WaitButWhy.com

This is where quitting as an exec is a “disadvantage.” Longer careers mean more exposure to these stories, leaving them permanently imprinted into your psyche. Often to the point that you hold them as universal truths, like the fish in the water. Here’s a small sample of the stories I encountered when I quit:

Expertise

  • You’re not an entrepreneur, you’ve had a corporate job your whole life
  • You’re not creative, you’ve always worked with numbers
  • Aren’t you scared of being damaged goods if you ever come back to the industry?

Financial

  • Are you ok with leaving during “peak earning years?”
  • Isn’t irresponsible to eat into your savings when you have young kids?
  • Aren’t you scared you’ll be broke?
  • If you want to have an impact, why don’t you make as much money as possible and give it away?

Societal/Cultural

  • When’s your vacation over?
  • Hit me up when you’re done soul searching
  • You can’t build anything meaningful unless you work 80 hours a week
  • If you’re working from home, we don’t need as much childcare (particularly acute for quitting moms)

Kate Bednarski, whose coaching clients include hard-charging hedge fund executives calls this “believing the myths.” These myths are always based on a scarcity mindset such as “How will I explain this gap in my work history” and “I won’t be able to advance my career if I take time off.” A longtime accounting executive shared her biggest “story:”

[Overcoming] the feeling that somehow we disappointed ourselves by not wanting anymore something we fought for for so long. I would say that most of the execs that reached the top or almost the top in their field in a prominent organization invested a lot to get there since an early age. Thus, walking away from that pursuit may trigger those kind of feelings.

And these stories will come at you like a game a dodgeball run amok – pelting you in the head as you wonder where you should be looking.

They will come from friends, colleagues, frenemies, spouses, parents, in-laws, mentors, and yes, even strangers at cocktail parties. Even internet trolls. But they’ll mostly come from within.

Now that our PSA is complete let’s attempt to answer the following question: How can a quitting exec apply the tools of an examined and intentional life to successfully navigate and thrive during this transition?

1. Set a firm “do not work” window

We’ve already established that you have some sort of financial safety net in the form of savings. Use it. Determine how much of your savings you’re willing to invest on yourself during that transition. You should be comfortable with it going to zero, but there’s a good chance that it pays off spectacularly in the form of new opportunities and the privilege of self-exploration. Calculate a number that takes into account your savings, insurance costs, projected expenses, a rainy day fund, and other sources of income (and this simple Google Sheet can help). Depending on your situation, this can be two months or two years.

Now commit to not taking a job during that window. Why? For starters, you’re going to be super raw. Chances are you’ve worked your butt off to get to that point and have never really experienced a true break as an adult. It will (and should) be disorienting. Your body is probably dying for some sleep, exercise – and the need to just be disconnected from the frenetic pace of technology. You need to restore your health in order to regain your footing. This alone is a damn good way to invest your financial safety net.

Another surprise in this early phase will be a surfeit of job offers – your first experience of abundance. You’ll have the newfound label of being “professionally in play” and it’s going to be damn tempting to seriously entertain each offer. Job offers will provide a nice ego boost, but remember you’re still raw; you’re at the first at-bat of a long game. (90 days represents 0.6% of a 40 year career!) If you’re truly looking to do something different, it’s not going to reveal itself in the first month. (There’s probably an exception to be made for a small amount of consulting, which can provide momentum, product-market fit, and a confidence boost.)

But I implore you to remember that in your “do not work” window you do not need to work. Remember that you built the financial plan, thus granted yourself permission to do whatever you want during this period.

2. Get a life coach

Tim Urban’s octopus is just the preview of the conflicting, complex and confusing issues that will surface once you quit. And I’m convinced that even the wokest of the woke are not equipped to manage the deluge of emotions. (Even if you think you are, remember that Tom Brady has a throwing coach, Tiger Woods a swing coach.)

The typical pushback against getting a life coach is: “I’ve got friends (mentors or a spouse) who play this role in my life.” This, IMHO, is flawed. First, the amount of time required (both in frequency and regularity) is high and your confidant(s) most certainly has their own lives, jobs and/or kids to tend to. It takes a lot of effort to listen to someone, let alone to hold someone accountable.

But more importantly, these confidants typically are invested in you. And they should be, they care about you deeply. But their investment in you can cloud their judgement, particularly when it comes difficult decisions. To get Sapiens on you, they are part of your story. You will presumably be faced with a decision where there’s some near term sacrifice (or suffering) that will pay off in spades in the long term. Those who care about you may not be willing to see you suffer, even for a short time period. (This is particularly acute when it comes to spouses as coaches.)

And the last pushback is that it’s expensive, often beginning at $150 per session. Yes, there are bad coaches, but usually when coaching “doesn’t work” it’s because the coachee didn’t give coaching the required mind space. My personal experience has included working with two coaches (Bednarski and Andrew Taggart) for almost four straight years and this investment has unquestionably paid off in multiples – both professionally, but more importantly in helping me find deep personal fulfillment.

3. Start a contemplative practice

I promise that you’ll feel emotionally overwhelmed right after you quit – and rightfully so. The “stories” will become pervasive, self-doubt will creep in, and the lack of structure will be disorienting. It’s imperative to cut through the noise and quiet the internal narrative. Only then will you free up the mind space to cultivate possibility. A contemplative practice is guaranteed to expand your toolkit for quieting the noise around you.

Meditation is all the rage today and you don’t need me to rehash its benefits. (Personally, a daily Transcendental Meditation practice of 40 minutes is my jam.) Here’s one anecdote from my conversation with meditation teacher Jeff Warren, who also co-authored Meditation for Fidgety Skeptics:

The metaphor I use is that of a mansion. We’re born in a mansion, the entirety is our inheritance. But room by room we begin to shut it up – we’re afraid to go in this room because we don’t like this, or this person hurt us and we don’t want to see them, or we don’t want to do this.  We’re closing down our experiences until we find this little tiny safe space under the stairs where we can hang out. And [meditation] practice is about saying “fuck that” I’m reclaiming the mansion.  Room by room, you go in and face each of these things. Meanwhile we’re having extreme experiences under the stairs, we’re not growing as people. 

Contemplative practices are personal and there are countless options including prayer and religion (in my case, Eastern Philosophy), poetry, yoga, journaling (a la Morning Pages), being in nature, community service, and playing an instrument. For the most part, these activities are atelic – the joy comes from the activity itself (like hanging out with friends) versus the outcome. For many execs, the sheer act of doing something with no end goal can feel very uncomfortable.

The philosopher Blaise Pascal wrote “All of humanity’s problems stem from man’s inability to sit quietly in a room alone” and these practices will be the kryptonite supporting your career transition, giving you power over your thoughts and the ability to challenge the status quo.

There’s no right or wrong practice, all that matters is a regular daily commitment. My personal rule is that I should dedicate the same amount of time to these practices as I do for fitness (for me, one hour per day). Bednarski also requires that her clients adopt a mindfulness practice, yet acknowledges that “a silent sitting practice may not work” for everybody. It can be as simple as “having your child be the subject of your mindfulness practice giving the child your full presence while with them.”

4. Set your non-negotiables

Hooray! So you’ve quit, no longer need to be tethered to your work email and are blessed with an unimaginable newfound freedom. But you’ll be amazed how quickly you’ll start feeling time scarcity. Most execs who quit have shared with me that they still feel rushed despite having no formal obligations.

And we have a four-letter word to blame for this: FOMO. Loss of identity-induced FOMO. Depending on the seniority of your prior role, you’ll start to question your prior relationships. “Was so-and-so my friend because of my ‘seat’? Or because of me?” Personally this FOMO resulted in me taking every meeting and attending every event (not to mention anxiously reading insane amounts).  Bednarski sees this pattern so frequently that she’s named it “borrowing pain from the future” – Buddhism calls it prapanca.

And with the snap of two fingers, poof, all of that hard earned freedom evaporates. Avoiding this trap is actually quite simple and requires you setting non-negotiable boundaries. Here are a few examples I’ve collected over my conversations with execs who have quit:

  • I only come into Manhattan X days a week
  • I will have dinner with my kids X days each week
  • If I only do one thing each day, it will be exercise and my contemplative practice
  • I will not check my email over an X hour (or day) period
  • I won’t meet with any assholes OR
  • I will only meet people who provide positive energy
  • I won’t wear a suit
  • I will sleep X hours every night

If you struggle to set these boundaries, remind yourself that you earned them. They are the fruits of labor of your accomplished career.

5. Give the people you love your best energy

The arduous path to becoming an executive unquestionably involved sacrifices. For the better part of my career, it was my highest priority and got first dibs on most of my attention and energy – at the expense of my wife, kids, and other loved ones. Whether I was on my Blackberry outside the delivery room, distracted during our Sunday family dinners, or just totally zonked out on a random weeknight because I had nothing left in the tank – the people I cared about the most suffered.

You now have the freedom and autonomy to change this. Don’t dwell on past transgressions, but remember two things: first, you earned it. But more importantly, this is yet another story to unlearn – that career growth must come at the expense of your relationships with loved ones. And with some distance from the corporate grind, some may be struck by an epiphany – I’m never going back to that lifestyle again – especially in a world of flexible and remote work.

So delete your e-mail app from your phone, hell, leave your phone at home when you take your kids to the playground or your partner on a date. One thing’s for damn sure – you may look back on your life and say “I spent too much time at work,” but you’ll never say “I spent too much time with the people I love.”

6. Follow the fun

I know what you’re thinking, “You can’t be serious – how will I prepare for what’s next, if I’m having fun?” This will be the hardest story to unwire. “It’s easy to get stuck in the normative What should I be doing,” says Sunil Arora, who coaches consultants, and both finance and tech company execs. Arora pushes them zoom out by answering the two questions: “How do you want to spend your time” and “what brings you joy and energy outside of work?”

The hallmark of a scarcity mindset is the belief that you must suffer for things that are worth having. Why should someone in their thirties go see action movies, take walks, (god forbid) play, take a class, paint, learn to DJ or skateboard. Thinking about fun will help reorient you to parts of your childhood that have been so deeply buried, that they may feel dead to you. But they’re dormant, not dead. And need to be awakened.

You’re probably asking yourself: what’s the point? How does this help me figure anything out? By tapping into this part of yourself, you’ll start to awaken. You’ll start to feel. To use investing terminology, these activities are rich in information content. And avoid the temptation to think that the activities themselves must turn into opportunities. No, I’ll never be a professional skateboarder, nor will I start a skateboarding business. But rekindling this passion will awaken my creativity, stretch me physically, expose me to subcultures I never new existed, and connect me with an entire new world of stories – all while bringing a smile to my face. The more fun you have, the more you’ll learn about yourself. And that’s a damn good investment.

So if you’re having fun, rest assured – you’re doing something right. Double down on the fun. And you’ll surprise yourself on how much you’ve changed once you’ve hit day 90. Who knows, you may stop keeping track as you accidentally (yet intentionally) launch into your next adventure.

If you’re in the midst of a career change, our Rad-endorsed coaches are incredible partners for the next leg of your journey.

Join our newsletter

Updates on everything new at RadReads.co