Leaping, Then Looking: Quitting A Job Without A Job

“Never quit a job without a job” is sage advice that I’ve heard for years, and yet, decided to ignore in 2017 when I left a steady gig to pursue the unknown. 

The decision to leave was perhaps one of the most difficult ones that I’ve made in my life.  I worked on a solid brand, enjoyed the work we were making, had good relationships with leadership and most importantly, really cared for the people on my team.   

Despite the above, at the end of the day I couldn’t shake the fact that after what felt like an eighteen year sprint, with my head down and no finish line in sight, I was, quite simply, tired.  

And beyond tired, perhaps also hungry for new experiences (ones I couldn’t put my finger on) that could help me grow both personally and professionally. 

Publishing my experience, given that we’re living through a pandemic and global recession, could strike some as a bit tone deaf.  Especially given that the author has been unemployed since Spring. 

And while I’d agree that this is certainly no time to leave a steady job (unless you want to leave and give it to yours truly), I suspect these days are leading to quite a bit of introspection amongst many people out there.  Somewhere between the 500th Slack message of the day, forced Zoom happy hour (“Is that a Rum and Coke you got there, Doug?) and onslaught of daily bad news delivered like the Hundred Hand Slap from E. Honda, they’re wondering if there’s something more. 

When the world and job market eventually return to normal, I think many people will be ready to pursue new adventures and search for meaning with great fervor, and with no guarantees, like never before.  The goal of this article is to share some insights from my experience in the hope that it helps someone out there navigate a similar journey. 

Craft A Plan Before You Quit

Before you pull the plug on a job to explore the unknown, it’s important that you sit with yourself for a bit to truly ask yourself what it is that you’re looking for.  In my case, I knew that I wanted to travel a bit internationally and domestically, spend some time with my wife/family and then jump into a job search that would push me into new experiences.  

So, I did just that.  I lined up some trips, mapped out two months of travel and determined that after my two months of downtime was up, I’d aggressively begin exploring conversations and new employment opportunities. 

I believe that formulating some sort of game plan is crucial, because it ensures that you maximize the newfound free time that one is about to encounter with chosen unemployment and also puts some focus on when you’ll shift energy back to a job search.  Without a plan, you can find yourself sitting listless, and that negates the potential growth that can come from stepping away and using free time to recharge, inspire and grow from a personal standpoint.   

Check Your Runway

Many factors contributed to my decision to quit my job without anything lined up including having no kids, no mortgage, a low overhead and a very loving and understanding wife. I also walked away at an age where I had a decent savings that I assumed would float me, as long as I took a reasonable amount of time off (couple months) and didn’t decide to YOLO it for the next three years, betting on horses and drinking champagne in white linens at exclusive Miami Beach parties (I couldn’t get into those anyway). 

Doing the math to see what your savings looks like to support your journey isn’t just wise, it’s essential.  

Take it from me and Birdman: Not seeing Ca$h Money hit the ol’ bank account on the 1st and 15th of the month isn’t comfortable, nor is taking money out of savings to support an adventure with no definitive ending. However, that’s the price you pay for choosing the unknown road for the comfortable path, and it’s something you’ll have to be ok with. 

If you don’t have a decent chunk of money saved up, I’d say leaving a paying gig is risky.  If you have a mortgage, kids in private school and lots of expenses, then you’ve probably stopped reading this article by now and I don’t blame you. 

Just know this:  When you’ll find another job is not guaranteed, so have an honest conversation with yourself about the money you have to support yourself and what you’re comfortable allocating to support your journey. 

If you have some cushion, great. If not, then perhaps now is not the time for a blind leap of faith if it’s going to make life more stressful.  

Assess Your Network

One final variable that I believe is smart to assess before leaving a job is your network.  While I was leaving a gig without an opportunity on the horizon, I was confident that my network, spanning 18 years in the LA market, would hopefully result in new opportunities. Fortunately, my hunch was correct and I’m extremely grateful to the connections that helped me freelance for nearly a year and a half before I landed in another full time role. 

This isn’t to say that you shouldn’t leave a job if you don’t have a strong network in a market. It’s just important to acknowledge that having a strong circle of former co-workers/managers is certainly going to aid the pursuit of new experiences one is seeking when they hit the street. Network can also play an indirect role with a financial runway, as mentioned above. 

SMOKEY SAYS: “ONLY YOU CAN PREVENT CORPORATE BRIDGE FIRES"

So, let’s say you’ve assessed the above and determined that you are indeed ready to leave your job to seek new and exciting experiences.  While I suppose you could give your employer the standard two weeks, I’d suggest giving them more notice than usual. 

When I decided to leave, I believe I gave my company about a month and half’s worth notice. The rationale was pretty simple….

I knew that it would take a while to potentially fill my position or determine a new structure.  Given that I wasn’t leaving for another job, I also was cognizant that there was no reason why I shouldn’t give them advance notice.  Most importantly, I didn’t want to leave leadership or my team in a bad spot.  They’d done a lot for me professionally and personally, so in no way did I want my departure to result in any strain on the team.  

I left on good terms and received nothing but support from the agency in return. In fact, they even offered me an incredible opportunity to come back as a freelancer, in a different capacity, several months later. I’m thankful for that and that opportunity would not have been available had I not handled my departure gracefully. 

That said, I suppose there are employers out there who could receive a month’s notice and counter with either a handshake and walking papers on the spot or a reply of “we’ll just take two weeks from you.”  It’s something to be considered when you approach your resignation and it’s not something that should be taken personally.

So, when you leave, do so with class. It’s a small industry and you never want to burn a bridge. 

You’re Free. But Who Are You?

Once you leave your job, wake up to a hangover from a going away party (I think those will still exist?) and find yourself newly free, you may stop to ask yourself “Ah, who am I?” 

I guess I naively didn’t understand how much part of me was tied into my professional identity until I found myself on a fishing boat several weeks into my sabbatical and someone asked me what I did for a living. I stuttered a bit and said that I was in advertising but wasn’t exactly working at the moment and struggled to put a finger on who I was as a professional.  Hmmm. What happened to the days of telling someone that I was in account management, followed by explaining that “No, I’m not an accountant, I manage the relationship between creative, client and, uh, never mind.” 

You may find, when you walk away for a moment, that you feel undefined. I’m here to tell you that’s ok. In fact, I quickly determined that it was important to let my previous title (Group Account Director) fall by the wayside in an effort to pursue freelance, or even full time, opportunities that felt different.  Along with that, I decided that within reason, it was OK to also not be tied to my former salary. 

If the goal is growth and new experiences, then I feel that it’s wise to drop some of the parameters that defined the old professional you. I ultimately freelanced as an Account Director on the Global Olympics, spent time copywriting at David&Goliath and landed at Facebook as a contract Program Marketing Manager, before ultimately landing a fulltime role at BSSP, ironically back in a position similar to what I originally left.  

I’m grateful to each and every person who made those opportunities possible.  Those experiences would not have happened if I had been tied to a title or number.  So, consider dropping your old corporate identity so that you can embrace new and unique experiences. 

In fact, don’t just take it from me.  Check out this article that my good friend Kim Mok wrote years ago. I think you’ll find it inspiring. 

The World Won’t Come To You

Part of the allure of leaving a full time role to spend time with yourself and seek new experiences is the thought that if you can just jump off the hamster wheel for a moment, perhaps you can find ample time for self-reflection, exploratory conversations and the ability to try new things out. 

While all true, what may not dawn on you is that all of those things take work as well. 

There was a foolish part of me that felt like my sudden availability and free-time would lead to an influx of new opportunities, which was admittedly stupid because I’m not a brand name CMO or agency A-Lister that graces the trades or articles posted on LinkedIn. 

Adam Silver, Commissioner of the National Basketball Association, did not wake up and say “Oh bully! This guy, Mike O’Malley, who launched the boldly re-imagined and stylishly designed Kia Forte, is on the market. This is one slow big man that the NBA could really use in our marketing department.” 

If you’re used to finding work while having work (like I was), then you are about to be re-introduced to the grind of announcing your availability, merchandising yourself, lining up freelance (or full time) work and essentially marketing yourself. 

It all equates to good experience, but don’t go in blind. It takes just as much work. 

In short: New experiences take effort. 

Get Comfortable With Being Uncomfortable

One thing that you quickly find when you leave a steady full time gig is that you’re abandoning stability for not only an exciting new chapter in life, but also for the element of uncertainty. 

If you’ve chosen to travel, or take some time to yourself first, you’ve certainly got some nice downtime in store for you.  However, unlike vacation where you know that you’ll be returning to a paying gig, you may also discover a looming feeling that consistently reminds you that sooner rather than later, you’ll need to find a job.

It’s a nagging feeling and it’s not comfortable, because there’s no answer to a timing you can’t dictate. Sure, your schedule may have checked July as the month that you’d like to work again, but you can’t be certain this will happen. 

If you’re freelancing, you’ll also be all too cognizant that once your contract is up, it will be time to land another gig.  Again, what you want and what will happen are not necessarily things you can control. 

My advice is to embrace the discomfort.  It’s important to become comfortable with the emotion of discomfort so that you can not only learn to manage the anxiety/stress associated with uncertainty, but also utilize it to motivate you.  Ultimately, tackling discomfort can make one more resourceful and resilient for future challenges and hurdles that life tends to toss at you. 

The Sustainability of Freelance

I’m going to go out on a limb and speculate that most who walk away for a bit comeback to find themselves on one of two paths.  

The first path is landing a full-time role in a similar or unrelated field.  Either way, this is great because you’ve hopefully re-charged your batteries, found new inspiration and landed somewhere where you’ll undoubtably be awesome. 

The second path is working the freelance circuit, bouncing from contract to contract.  This path is good, because it allows you to encounter new experiences as you continue your journey of discovery and also provides nice pockets in-between contracts to travel, take time off, spend time with family, etc. 

However, I will caution, especially for Account folk, that while attractive, the world of freelance provides no guarantees.  When it rains it pours, and sometimes it feels like there are no shortages of roles out in the market. Other times, opportunities can appear shockingly sparse and one’s inbox transforms from the Rain Forest to Death Valley. 

I loved my freelance experiences and wouldn’t trade them for anything. 

However, I also know that long term, I’m not one who could sustain years upon years of freelance. At least, not as a senior account person. 

It’s wise that you give this some thought as well. 

 Life Won’t Wait

Leaving a job without a job is not a decision to be taken lightly. It takes great introspection within oneself to determine whether or not this is the right move for you and your future. 

There are days that I wonder if I made the right decision, both professionally and monetarily. 

But, at the end of the day, I have absolutely no regrets. 

I traveled to foreign places, grew professionally through a diverse array of experiences and most importantly, met a host of new people through my freelance circuit and full time role.

If this year has proven anything, it’s that life is unmercifully random.  Short for some, long for others, but undoubtably random. 

If there’s a nagging voice in the back of your head that is pushing you towards something new and unexpected, then I’d say take the plunge and have faith that the world has new things in store for you. 

Prior to taking a dive into the unknown, I had a conversation with my brother as to my thought process and the back and forth dialogue in my mind. 

He was quiet and simply said, “Sometimes you’ve got to bet on yourself.” 

I’d say that’s damn good advice and a bet that all of us should be willing to take. 

Good luck.  I’ll be pulling for you.