Are You Tired Yet?

I need your help and advice.

For the past month or so I’ve been talking with a friend of mine that is stuck between a rock and a hard place. She’s super talented, accomplished, respected and sought after. She is a crazy combination of perfectionist, a little bit OCD and a liberal dash of just plain awesome.

She likes where she works mostly because she’s comfortable there and she likes the friends she’s made. She doesn’t see a long and glorious road ahead of her, but it’s paying the bills for now. She is valued there and is known as one of the most valuable players. She no longer wakes up each morning looking forward to work, in fact, the dread of Monday morning has now crept into Sunday.

My friend is not perfect. Although she is about as close as I have seen in her field.

You probably know someone similar. Someone who is a swan in the duck pond. Someone who can do something fantastic if they only took the first step. If they only trusted themselves the way everyone else already trusts them.

I’ve advised her that it’s time to move on. But she’s not so sure.

If you haven’t watched An Invocation for Beginnings, I urge you to. It’s 3 minutes that will probably make you feel something deep inside you twisting a little.

Change is difficult.

My seo/geek/blogger crush Lisa Barone threw me for a loop when she announced that she was stepping down from her founding role at Outspoken Media. It was shocking for two reasons; 1. I think of OSM as Lisa and 2. She has no plan (at least publicly known) for her next step. As Dan Rather would say… courage.

How do you know when it’s time to move on? For me it was when I read The Dip

The old saying is wrong—winners do quit, and quitters do win.

Every new project (or job, or hobby, or company) starts out exciting and fun. Then it gets harder and less fun, until it hits a low point—really hard, and not much fun at all.

And then you find yourself asking if the goal is even worth the hassle. Maybe you’re in a Dip—a temporary setback that will get better if you keep pushing. But maybe it’s really a Cul-de-Sac, which will never get better, no matter how hard you try.

According to bestselling author Seth Godin, what really sets superstars apart from everyone else is the ability to escape dead ends quickly, while staying focused and motivated when it really counts.

Winners quit fast, quit often, and quit without guilt—until they commit to beating the right Dip for the right reasons. In fact, winners seek out the Dip. They realize that the bigger the barrier, the bigger the reward for getting past it. If you can become number one in your niche, you’ll get more than your fair share of profits, glory, and long-term security.

Losers, on the other hand, fall into two basic traps. Either they fail to stick out the Dip—they get to the moment of truth and then give up—or they never even find the right Dip to conquer.

Please let me know in the comments how you figured it out in your life.

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  1. First: [Mental Note: read The Dip]

    Second: I’m no expert on this but…we all get bored, unchallenged, unappreciated, “stuck”. Some of move on, some of us stick it out, some of us keep plugging away and persevere. There is no one cookie-cutter answer and everyone’s mileage is different. But per:

    “winners do quit, and quitters do win”

    Winners also have a plan. Quitters don’t.
    Winners are like chess players and look a few moves ahead. Quitters only see the immediate picture.
    Winners look at all angles and can remove emotion from the equation – they are disciplined and committed. Quitters are irrational and impulsive.

    Eventually, we all quit (or are asked to leave), but I have seen many good people leave positions, without thinking through the big picture, having a plan, and not assessing the implications of quitting. More often then not they wake up 3 months later thinking “Oh, shit, what the efff have I done” and get trapped spinning their wheels in a series of jobs that are equally no better than the ones they left.

    As far as I can tell, the only really sweet gig is lead singer of U2 and I’m sure the current guy holding that position would probably give you a hundred reasons why his job sucks.

    So, I would ask is your friend motivated by opportunity or by boredom. If its the former- then be line up your ducks and move on. If its the latter, she’s got more work to do before making the leap*

    * If she’s got a mortgage, kids, etc, she’s really really really got to think things through first.

    • Yes, read The Dip. I have to disagree that boredom isn’t a good enough reason to move on. You can’t do inspired work if you’re bored. You don’t look forward to changing the world when you’re bored.

      We all have responsibilities that we need to take into account, but being miserable 8 (or 12) hours a day certainly can have a deleterious impact on the other aspects of your life IMHO.

  2. Winners have a plan, but may not share it with the rest of the world until they are ready to put it into action. I wholeheartedly believe that’s the case with @lisabarone, just as it was with @oilman recently, and with me (@jennyhalasz) a year ago.

    The bottom line is you’ve got to be happy in your life. If your job sucks (or maybe doesn’t suck but is causing you to lose sleep at night and dread Mondays), then there’s got to be a better way. I think I know who you are talking about… she needs to assess the situation and make a change. Sometimes it’s possible to make a change without quitting, and she should explore that as well.

    As for thinking of your family… if you are unhappy all the time, or worrying about work, you aren’t setting a good example for your children and you may not be fully “present” when you’re with them. Since I quit my “safe” job a year ago, my entire family is happier.

    • I agree with the concept of “there must be a better way”. No one needs to be unhappy at work on a regular basis when they are at the top of their game. Game changers can’t let the machine dull their sharp points.

      The fun thing about writing about an anonymous person is that everyone can project this situation onto someone they know in a very similar situation. So it doesn’t matter if you know exactly who I’m referencing or not, you know the situation.

      • “it doesn’t matter if you know exactly who I’m referencing or not, you know the situation.”

        Amen to that!

      • “it doesn’t matter if you know exactly who I’m referencing or not, you know the situation.”

        We all relate to this because we have all been this person. My point is that pragmatically addressing unhappiness at work is better than just quitting without a plan. Unhappy with a paycheck is always better than happy without a paycheck. Especially in today’s economy.

        Just keepin’ it real ;)

        • @deanshaw – I appreciate where you’re coming from, because as an old geezer I’m in that situation. Knowing that, I started laying a groundwork 5 years ago so I can focus on doing my best work at places I really want to be.

  3. Great post Phil. If only everyone loved what they were good at and chocolate chip cookies didn’t make our thighs fat. Having gone through this myself recently, I suspect your friend has some inkling of what will make her content, even if she hasn’t figured it all out yet. She might have to close some of the doors that keep hitting her in the head or take a severe enough blow, before everything becomes clear, but it will. Kudos to her for realizing there is another calling out there for her. My advise to her would be – she will know when the time is right, grab it and run like the wind.

    • Mmmm, cookies :-)

      I think since it’s her first “real job” she has no experience with all the fun and excitement of changing jobs. The pit in your stomach when you have to tell your boss, the wave of relief that floods over you afterwards, the emotional high of realizing all your friends want the best for you, the honeymoon period of a new job with a new company and the realization that any day is another chance for greatness – as soon as you make a decision to be great.

  4. Rob McAlister says:


    I have no clue what you’re talking about here Phil, but thanks for posting it anyway.

    • I know one thing for sure, you and I have seen both ends of the scale, and the “awesome” end of the scale is a hell of a lot more fun :-)

    • That reminds me. I owe you a thank you! You were absolutely right about your advice on not letting food guide you through the change. It is soooo easy to do. Your voice in my head has helped me many a day as I reached for ice cream, cookies …. comfort foods. Thanks!

  5. Great post, Phil.

    As long as we are throwing out cliches…the grass is always greener on the other side.

    Having been at the same post for 5 years, I have seen a lot of really great folks bounce around repeatedly over a short timeframe. There are pros and cons to that, and some people can afford to do that and others can not. Just be careful to not get caught in that loop forever as your search for that perfect gig. It takes truly talented people with really invaluable skills to do that. We all think we are special…but only certain people will continue to rise to the top of those resume stacks.

    Work is work, and at some point we all get bored. It’s the culture of the company that helps us overcome that. Be picky about the cultural fit if she chooses to head towards greener pastures. At the right company, the people around you and your environment will help you get through the good days. It should also be a place where you are comfortable to speak up and discuss your ‘boredom’ and find a new version of your role or new set of responsibilities that gets you fired up again.

    Just my two cents. Best of luck to her.

    • I agree 100% JT – for me it’s all about culture. The truth is if you don’t fit in with the culture you’ll be miserable. Sometimes the person changes, sometimes the culture changes but either way, when that breaks down it’s a problem.

  6. I always treat my professional relationships the same as my personal ones. Jobs are like boyfriends or suitors. You spend over half your waking life at your job, not with your husband. It might as well be a second significant other!

    If your job was a person, and you were in a relationship with them, could you spend the rest of your life with them? How about three more years? Do you wake up every morning wanting to gnaw your arm off because your relationship is so unfulfilling? Are you staying with them just because they help you pay the bills? Because it makes you feel safe and comfortable, even if it is a miserable comfortable? Do they enable your worst habits? Do they feed your fears and cut you down? Do they make you feel like you have a purpose–even if it is just taking care of them?

    If they aren’t doing everything they can for you, if they don’t value and respect you, if they aren’t willing to meet you half way, it’s a bad relationship, and you need to move on. Imagine yourself looking back on five more years of this in twenty years. Will you feel sad?

    I was in a bad personal relationship once. I was having trouble cutting the tie. I was at art class one evening and I explained the situation to my older, more experienced female classmates. They both shook their heads. “You are too young to be agonizing over something that will be so trivial in hindsight. Cut the bond and live your life. Don’t settle for this, honey. There’s more out there than this.”

    There is more out there than this.

  7. Geoff Corey says:

    My criteria is pretty simple:
    1) When it is affecting my health.
    2) When the business is not viable.
    3) When it is no longer challenging.
    4) When it is not enjoyable.

    Health is usually affected by stress and constant long hours.

    If the business is not viable, then get out. The reward for sticking out on the last day is all the good jobs were taken by your peers that had enough foresight to stop wasting time. If you really don’t believe in what the company is doing and will be successful in the marketplace, then you shouldn’t be there.

    Not challenging can come in many forms but in one case in a large corporation we finished the product and we had nothing to do as a team. After a month I went to a new job. Breathers are nice but 4-5 weeks is not doing my career any good.

    When it is no longer enjoyable has a simple litmus test. If you wake up and dread going to work, update your resume. Doesn’t matter why you hate your job, you do. No psychotrist is going to hypnotize you to make you think your going fishing everyday. Get out because you likely ignored the #1 reason.

  8. I generally refer to this post from Ross Hudgens.

    One statement stood out to me when I first read it:

    “And if your current gig doesn’t give you the flexibility to be a “linchpin”, quit, because your job sucks, and you deserve better”.

    I realized I would never be a linchpin for an in-house position where I was able to make them dominant in their space. Every opportunity they had, C-Level folks would credit MY leads to another channel. It took me 3 years to realize they weren’t doing that because they were stupid. They did it so they wouldn’t have to pay bonuses or raises. Also they did it because that was how they chose to motivate, by fear and naysaying. Once I determined that for every victory I accomplished, they would move the goalpost and claim foul on me, it was time to go. I made pretty well there and could come/go as I pleased, but what was missing was a sliver of recognition for the value I brought them week in and week out. I wasn’t expecting a pat on the head, I was expecting a bit more latitude in the overall marketing strategy for proving success despite their efforts to hide it. They even refused to share *their* marketing data with the internet department because it was so manipulated to favor other channels and they knew it. I jumped ship without looking because it forced me to look for the right opportunity instead of settling for what paid well. We’re internet marketers, so that means we are in demand and there is a place for each of us at someone’s table. What we decide to eat while there, depends on our appetites and manners. “May I be excused”?

    • The truth is we all like some positive feedback for doing a good job. It doesn’t have to be anything crazy, just enough to feel the appreciation.

      When that stops you need to figure out why? Sometimes it’s them, sometimes it’s you. In either case it’s probably time to move on.

  9. Alan Bleiweiss says:

    At this point in life I have the luxury of having the ability to look back over more than three decades of my work/life journey to see where along that path I can relate to your friends situation. While I only know what you’ve conveyed, and thus not the whole picture, there are commonalities taken from that.

    Something I’ve shared with those who have sought my guidance through the years is that we need to learn to listen to our own hearts – pay enough attention to recognize what we’re being told from within. It’s not easy given the need to pay bills, to maintain responsibilities… And it’s made more challenging when we live in a society where the “common sense” approach is typically to either “buck up and deal with it – life’s a bitch” or “you’re irresponsible if you don’t put in the footwork to line something up before you jump”…

    More than once I’ve been blessed to be able to find a way to have a shift occur without leaving my current employment. To do that I’ve needed to change my own perspective, or sometimes to speak up about something that’s been eating away at me, or a combination of both. And the end result allowed me to stick around longer, reinvigorated, refreshed, excited.

    Other times, even when I’ve done that, it wasn’t enough. My heart continued to nag at me. My intuition continued to prod me to move on. And when I’ve listened, trusting that “I need to do this or I’m going to implode”, it’s always worked out. Not always easy, not always painless. Yet long term, it’s always led me to that next level in life.

    A really big part of all of this – either path option, has been to take the time to identify what it is I really like about the work I’d been doing, the job, the workplace, the people and the process, and what it was that I didn’t.

    From there, I intentionally set a vision to have my next experience (either at the same employer/work experience or at the next one) to have those things I disliked the most replaced with their opposite experience.

    I spend less time on the form of things and more on the feeling / emotional / intellectual aspects. That’s key for me because I don’t want to get stuck into forcing my inner needs on the outside appearance of what I do or the place I’m offered to hang my hat.

    And lets not discount the concept that at least for some of us, it can sometimes mean that we go from being an employee to being a consultant or self-employed. Or from being a consultant / self-employed to being an employee…

    The bottom line here is guidance is invaluable from others, yet ultimately, the more we pay attention to our inner truth, the sooner we get to that next level. And I wish your friend a heartfelt blessing that they find that next place along their journey!

    • Thanks Alan. I agree with the point that it ultimately has to be a change that you feel inside.

      Change, even when you feel like it will be a change for the better, is still difficult.

  10. My approach – the moment I feel something isn’t right (could be one significant circumstance or a combination thereof), that’s when I know it’s time to start making plans for that change. Now, whether it’s impulsively or well-thought out, it depends on the circumstance. If I’m so miserable that I dread Mondays, dread what I’m doing, and my health begins to suffer, that’s when I know it’s time to make a drastic change and submit that 2-weeks notice even if the plan is to take 2 jobs (or 3) until I can find a new full-time experience to replace the dreaded one. BUT, if I’m just feeling something isn’t right and know it’s time for a change, I begin to plan my exit from one and entrance to another fantastic full-time gig. Either way, I make a decision, stick to it, and more importantly, have an end-goal as a result. Whether it’s taking up 3 jobs to make ends meet until a better job comes along or it’s preparing for the next best thing, there’s always an end-result; not a “hey, I hate my job right now. I’m going to quit and see what happens…and GO!” attitude. Of course, this is also coming from a faith-driven person too who believes and trusts God’s got His plan for her as well. Not sure how I’d be if I didn’t have that too.

    Good luck to your friend. I’ll be praying for her decision. :)

    • Having a plan is always the best way to go. It’s fantastic to have something better to walk into on the day you tell the boss you’re done. But what if you have an opportunity but you’re unsure – should you take the leap of faith?

      Whether God has a plan for her or not, she needs to have a plan for herself! I love that you mention having the long-range view of where you want to end up – that is critical IMHO.

  11. So much can be and has been said here. My experience is that if I am not being asked to work within my strengths and expertise, my boredom becomes quite a catalyst for me to move on, especially when those folks in charge are not authentic in disclosing job duties and expectations!

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