10 Things I Learned From Quitting My Job. Regret Wasn’t One of Them.

Taking the path less travelled

Taking the path less travelled

To be fair, I didn’t QUIT work.  I moved to a smaller creative agency and a four day week with the freedom (intellectual and physical) to thrive.

The “bonus” 5th day is MINE, not owned by work or responsibilities.  A space to rekindle lost interests, fine-tune life’s vision and celebrate meaningful achievements.  An “innovation lab” of one.

So what have I learned over the last three months?


Despite the fact that I loved my last job, and the people I worked with, I’d outgrown my surroundings.  This realization came about three years ago but I was paralyzed to act on my insight.  Terrified that leaving a “secure” work environment would make me homeless, hungry and unable to provide for my child–it was easier to plod along treading the rhythm of someone else’s drum.

The thing is, since leaving big agency life to pursue a routine with less structure and perceived security, I feel completely at ease. FEAR has been replaced by FREEDOM.


Most people can do absolutely awe-inspiring things.  Sometimes they just need a little nudge.”  TIM FERRISS, 4-HOUR WORK WEEK

Impetus for change came when I was presented with a job offer that had huge potential but also risk.  A small agency meant less security, but also less stress and more flexibility.  No opportunity was going to fulfill all I was looking for…it gave me the chance to have more autonomy and explore personal projects.


Agency life can be manic.  Productivity is often mistaken for progress. Being overworked and reactive is not a sustainable path for success.  Having time to step back, assess situations and explore new approaches is where real growth comes from–and ultimately innovation.


Surround yourself with talented people–and those who share similar beliefs.  It’s a lot easier to thrive in a place where your values aren’t shunned–but are celebrated instead.

Leaving a job doesn’t mean leaving your colleagues.  That’s what coffee shops were invented for (oh, and LinkedIn).


When you work for a company for an extended period you absorb its culture, process and language.  Like a family (sometimes nurturing–sometimes dysfunctional) it defines our role, contribution and validation in the workplace. However, agencies are not that unique.

Beyond their walls hundreds of other creative worlds exist.  After conducting an audit of over 100 agencies in SF alone I concluded that there’s really not much difference between them–most offer combinations of advertising, branding and digital (with different clients and emphases).  The trick is to find an agency that is congruent with your values and delivers what excites you.


Don’t underestimate yourself.  You are better than you think.” TIM FERRIS, 4-HOUR WORK WEEK

A while back I discovered the Dunning-Kruger effect, a cognitive bias that showed how unskilled individuals suffer from illusory superiority, mistakenly rating their ability much higher than average.  It miraculously explained much of the frustrations present in client-agency dynamics.

What is more “Actual competence may weaken self-confidence, as competent individuals may falsely assume that others have an equivalent understanding.”

Suffice to say, I’ve gained a lot of confidence in my own abilities.


In an industry where statistics, data and research second-guess creativity – intuition is often overlooked. From judging solutions to evaluating the next career move–instincts count. Always trust that what feels right, is right. This also applies to sales and account management–engage conversations from a place of authenticity and you can’t fail.

Also, don’t let other people’s limitations limit you.


When you’re in the maelstrom of constant deadlines and deliverables it’s hard to breathe. Having the time to step back and focus helps to improve efficiency, juggle priorities and be truly creative.  It’s the difference between getting shelled in the trenches vs. strategizing the next assault from a safe range.


A recent publication by the Society of Digital Agencies (SoDA report) suggests that money isn’t the #1 factor for employees.  The top three motivations are:

  • Interesting work
  • Culture
  • Work/life balance

I second that.  Time is the new currency for success.


Since turning 40, I feel more confident, validated and invigorated than ever before. Experience brings clarity to unhelpful behaviors; wisdom provides insight to making better choices.  40+ harnesses this knowledge while still having the energy to pursue dreams yet realized.

And guess what?  You get to pay it forward.

4 responses to “10 Things I Learned From Quitting My Job. Regret Wasn’t One of Them.

  1. Thank you for this. I left the agency I had been working in for 10 years to work as a freelance consultant, I just could not take it anymore, the lack of sleep, the ridiculous deadlines and a very toxic work environment. Sometimes, specially on the months I don’t have so many projects, I regret it. This helped a lot, made me feel good and helped me remember why I quit in the first place

  2. Thanks Monica. Freelance is daunting, not sure I’m ready for that yet. However, being out of a toxic workplace definitely feels good. I wish you every success.

  3. Hi Rachel…

    This may seem a little off-topic, but I came across your post after searching “regret quitting dream job” and would like the opinion of a person with no perceivable bias to my situation. I can get a bit wordy, so I’ll try to cut to the chase as much as possible…but If you could give me your thoughts in regards to what I have going on in my career situation I would appreciate it!

    Last March I quit what I thought was my dream job, being a police officer. I hadn’t made it to the streets yet, only 10 weeks into the academy and yet all of the bullshit really started to add up quickly. I was tired of being screamed at daily and humiliated in front of 36 other people on a regular basis all in the name of “thickening my skin” as the public would be 1,000 times worse so they said. I didn’t see it that way, I cared about what these 36 other people thought and felt that my life was expendable for theirs even though in retrospect I don’t know if I could say the same for them. The people on the street wouldn’t necessarily mean anything to me and I would be able to easily deflect the endless assault of threats and insults from Joe The Drunken Schmoe.

    So after 10 weeks of what would be considered an award winning civil case for creating of a hostile work environment, I quit and over the past 9 months I’ve had serious bouts of depression over this situation. I think about it every day and some days I feel like I really want to go and try this again and then moments later a bad memory or 2 will come up and I’ll ask myself if I’m going crazy. It’s almost like I have Stockholm Syndrome, wanting to get myself back into what I know is a stressful, heart wrenching experience for me and I can’t seem to make heads or tails of this.

    Of course I’ve talked this over with numerous family members and friends, and pretty much all I get is what seems to be comforting thoughts and praise about how I gave it my best shot. I can say that at the time I followed my intuition and I do genuinely trust my intuition as it has gotten me out of many bad situations and led me towards many great situations, but I don’t know why I still have these lingering thoughts about trying to be a police officer again knowing how bad it can be? I just feel like I have the heart to really help people and not look at every last person as if they were going to kill me like they train you to think. I must admit that I am an adrenaline junkie and the fast cars and guns are a highlight as well, but that is far from the main motivation I have to be a police officer.

    See…things get wordy with me, but any feedback/thoughts you may have would be great.


    • Hi Chuck, thanks for reaching out. Not sure I’m in a position to offer advice, but I’ll share my take.

      Life is complex – if only we could have an instruction manual to navigate the myriad of choices.

      Seems like you’re living life as honestly as possible – which is all we can do. Doesn’t make it easy. But it does mean that we have a better chance of arriving at contentment.

      I believe that using intuition isn’t just about making a single decision at a particular moment in time. More often than not it gives us the insight to try again, with a different perspective. Leaving your training at the very least helped you to disengage from the reactive state you were in. From there, you’ve been able to test out how strong your feelings are. After 9 months of distance some key desires have remained. It doesn’t mean you were wrong to leave, it means that you’ve validated what is important to you.

      Sounds like what you desire most about the force are the opportunities it may create – the excitement, the helping people, the camaraderie etc. Yet the path to reaching them is particularly challenging.

      Sometimes we’re faced with contrasts in the extreme – in order to unlock the good parts of policing, you have to sacrifice the values you hold important (self respect, humanity etc), and brutalize yourself in the process. Only you can determine what you’re prepared to endure – maybe the last 9 months have helped you prepare more fully for that challenge.

      However, identifying what attracts you to being a police officer is key. It may help you forge a different path (or paths). Maybe a single career that delivers upon all of your desires isn’t possible. Perhaps you can satisfy each one separately: become a social worker to help people; race cars on the weekend; spend more time with friends….?

      The trying is part of the process. With each new attempt we gain further clarity into what’s important.

      One last thing to mention, any kind of institutionalized body (police, armed forces etc) is not set up to value the individual. It would be an uphill battle for anyone to retain a sense of humanity and warmth within its structure…especially in today’s social climate. If you truly value connecting with people and having that reciprocated…you may be setting yourself up for disappointment.

      There is no “one” way in life. Many paths lead to fulfillment…seems like you have the ability to question decisions and the courage to act – which is half the battle.

      Good luck on your journey.

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