Knowing when to quit isn’t easy. Most of us have been conditioned to believe that persistence against all odds and steadfast dedication should be revered above all. But there’s tremendous power in knowing when to throw in the towel, so that you can make space for bigger and better intentions.

In this post, we’ll explore how to quit your job gracefully so you can focus on a complete career change. Plus, we’ll demystify some of the fears behind going all-in and quitting (and why quitting doesn’t make you a quitter).

Quitting for a Complete Career Pivot — It’s Not as Scary as You Might Think

When I talk about “quitting,” I’m not talking about resigning because you got an offer from a different company to do virtually the same thing. I’m talking about pivoting out of your comfort zone and taking a bold career leap, whether that’s going back to school, taking a career-changing tech bootcamp (like I did with General Assembly), traveling the world, or some other form of a hard left-hand turn.

The stress I felt walking into my office on Monday, October 2, 2017 was almost too much to bear. “Today is the day I quit my dream job,” I kept muttering to myself on what would be my final morning commute in between deep breaths.

Fresh off a beachside eureka moment just a few months prior, my early conviction about attending General Assembly’s Web Development Immersive program (now called their Software Engineering Bootcamp) began to wane in the days leading up to my planned resignation. 

I made thorough preparations. I compared the pros and cons ad nauseum. I prepared a mini speech, as if I would have some grand audience hanging on my every parting word. I ran through my whole script with parents, siblings, friends — whoever would listen. To paraphrase, it went something like:

“I really appreciate the opportunities you’ve provided me, but I need to resign and leave here as soon as possible for a big career pivot into an immersive coding bootcamp. I’m very sorry, but I can’t give you two weeks because I have a mountain of pre-course work to complete. How does two days sound?”

I felt sick to my stomach as I agonized over every scenario. How could I possibly walk into that den of wolves with such a ridiculous proposition? The shame and embarrassment were almost too much to bear. In many ways, my identity was wrapped up in this notion of being a sales trader and here I stood, ready to leave it all behind.

What would my boss say? What would my peers think of me? What would they say behind my back? All of that judgment kicked around in my brain like a game of pong.

As soon as our morning research call was over, I pulled my boss aside to chat in a conference room. Truthfully, most of the conversation is now a blur to me. I can only imagine the incoherent thoughts I managed to stammer out. The discussion couldn’t have lasted longer than five minutes. Lo and behold, all of my worst nightmares didn’t come true.

What I can recall was his genuine happiness for me. He agreed this was a smart move at this point in my career. He shook my hand reassuringly saying, “Don’t worry about the two weeks, take off today if you’d like.” (Spoiler: Don’t expect this to be the case for you — this just happened to be the norm for certain sensitive roles in finance.)

“That wasn’t so bad…” I thought. Was it really that simple? All that agonizing over a measly five minutes?

“We suffer more often in imagination than in reality.”

— Seneca

As it turned out, most of my peers were happy for me too. Others may have been glad to see me go. But an epiphany quickly dawned on me as I said my last goodbyes. 

What the hell did I care what any of them thought? None of their opinions, whether true or false, actually mattered — this is my life. Turn the damn page and let go already, Tim!

I can’t explain the joy I felt running down that office stairwell. I practically skipped to my car. I felt like I’d been freed from prison, beaming with confidence and newfound purpose.

Tips to Break from the Chains of Your Current Career Path

So how exactly does one quit with grace? How do we truly liberate ourselves from the shackles of our current career paths?

Have a Plan (and Make it Known)

For one, have a freaking plan and make it known. However, I will advise — you shouldn’t be completely transparent.

In the months leading up to October 2, it felt like the writing was on the wall about my exit. I’d hinted to peers and various leaders about online learning opportunities to develop more attractive skills and domain expertise in tech. I subtly educated them about coding bootcamps and how my friends had achieved success after completing them.

After some careful broadcasting, my colleagues began to agree coding skills were more attractive in today’s job market than a Series 7. By positioning bootcamps as a viable option, I knew my departure would feel more normal. While you can’t wait forever to make your move, you do have the option of playing the slow game. Bluffing your intentions or tactful telegraphing can be a helpful tool prior to revealing your cards.

It’s a common sales tactic: advance your agenda in such a way that leads your target audience to believe it was their idea. Dripping ideas in this way at opportunistic moments will plant the seeds for your eventual exit to feel less abrupt or mysterious.

Build a Good Relationship with Your Boss 

An even easier trick that can help settle your nerves and produce cleaner breaks is simply having a good rapport with your leadership. I realize that may be hard for some who suffer from the big, bad mega-lord type of boss, but hear me out.

The minimum requirement here is having a reputation for being punctual, thorough, and reasonably reliable. Mutual respect goes a long way when quitting-time comes. Despite the agony of anticipation we feel when preparing to quit, the truth is most people want you to see you succeed — especially if you’re not perceived as an a-hole.

I was fortunate to have developed a cordial relationship with my boss, which made it an easier sell. If you’ve burned some bridges with your manager, take steps to mend them well in advance of your departure. You’re going to need solid references later on, so don’t end your tenure on a sour note. It could come back to haunt you later on.

And for the bosses who simply can’t take the high road or be supportive, you can only use their disdain as motivation. Rest assured, revenge will be sweet (and lucrative if you play your cards right).

Level Up Your Pros and Cons List

Another tip — I mentioned listing pros and cons earlier, the classic exercise that most are familiar with. However, there’s a 2.0 version I highly recommend checking out.

The practice, coined by Tim Ferriss, is called Fear Setting. Rooted in the stoic philosophy of controlling only what you can, this listmaking method goes beyond spelling out your worst fears, and explores the true cost of inaction.

Most disaster scenarios can be mitigated or quickly remedied, but the paranoia of needing to think through every edge-case can be paralyzing for most. Fear Setting enables you to openly air your grievances, while simultaneously creating a backstop against the worst case, in order to free up your receptiveness to opportunities.

We rarely consider the opportunity cost of sticking with the status quo. Ask yourself, “Who will I be in six months if I continue on this path?” Oftentimes, your answer is much scarier than a breakup with your boss.

Remember — There’s Never a Perfect Time to Quit

A final piece of advice — there’s never a “perfect” time to quit. You can certainly prepare, but eventually you must walk the plank.

Fight the fear. If your conviction is strong and you can truly picture your future self on the other side, don’t let fear of uncertainty hold you back from your ambition.

To this day, I still vividly remember the terrible anxiety I felt leading up to October 2. It’s a real visceral feeling, and I won’t lie to convince you it can be ignored. Instead, I’ll share a final quote that packs a Tyson punch’s worth of wisdom when you’re feeling stuck:

“Nothing diminishes anxiety faster than action.”

– Walter Anderson

Inaction is like a strong riptide; one must let go and swim sideways to shore, rather than fight against the current and remain stagnant. Doing nothing might seem like the easy route, but you’ll never forgive yourself if you let fear or judgment overtake you.

By the same token, intention can’t be manufactured inorganically. Don’t jump just because everyone else is doing it — you have to want it for yourself. 

It doesn’t hurt to use tools and resources available to you, but ultimately you must make the choice. In the end, quitting doesn’t have to be so scary. Make a plan, leverage your goodwill, and consider the risks before you take the plunge.

This is your future and only you can shape the clay into the final product you’ve envisioned. As someone standing on the other side, I can tell you with full confidence that all the pain was worth it in the end.

For me, the next step was diving headfirst into General Assembly’s full-time Software Engineering Bootcamp. Maybe that’s the same path you’re looking to take. Or maybe you’re still exploring your options. If that’s the case, I highly recommend checking out all GA’s free info sessions available that might create the spark you need to say goodbye to your current career and reinvent yourself in a new tech career. 


A few years after graduating college, Tim realized his lifelong dream of becoming a sales trader. But after reaching the summit, he quickly realized his dream career was the wrong fit — for a litany of reasons. So at 27 years young, he had a “eureka” moment, quit his supposed dream job, and attended a General Assembly coding bootcamp. It was both the most radical and important decision he’d ever made. With help from General Assembly, he re-learned how to learn immersively, acquired domain expertise, and landed as an early employee at a scrappy tech startup — where he still works today as a Team Lead & Sr. Solutions Engineer. Check out Tim’s blog for everything from advice on choosing a coding bootcamp to no-nonsense LA restaurant reviews.