I have a client (we’ll call her Candace) who came to me with a conundrum that she felt was practically unsolvable.

The past 5 jobs she’s had have all turned out the same way … unfulfilling, uninspiring, and with bosses that are domineering and difficult to work with.

Each job begins and ends the same way: She lands in a new job because she got fed up with the terrible leadership and work environment at the old job. Eventually, she gets fed up with the new job, for the same reasons, and decides to try something different … only to have the cycle repeat itself once more.

Exasperated, she asked me, “Why does this keep happening to me??”


Before I launch into how I responded to Candace, I want you to understand how ridiculously normal this question is.

How many of you feel like you’re banging your head against a brick wall, having the exact same circumstances show up again and again, with no idea of how to make it stop?

Stubborn patterns can show up in any way you can imagine.

For some people, it’s romantic relationships. You know the type … the guy or girl who is forever manifesting the same old drama, just with a new person.

For others, it’s health. There’s always that one person who’s telling everyone about the latest fad diet they’re trying … even though the last six they tried were a bust.

It can also show up with money, family, power, career … the possibilities are endless.

For me, it was always about my career and money.

No matter how many jobs I hopped to, I’d always end up in an eerily familiar scene: Getting way underpaid to do a job I didn’t enjoy at all, for a cause I couldn’t support, with people I couldn’t really connect with.

I’m sure you know what your particular “thing” is without having to think hard about it. Keep that in mind because …


“Why does this keep happening to me?” is the completely wrong question.

Instead, I asked Candace, “How about you start asking, ‘Why do I keep happening to this?’”

This stopped her in her tracks for a moment.

Because, like most everyone else, Candace came programmed to think of herself more at the mercy of the world instead of in control of what’s going on around her.

That’s why her first inclination when things went wrong at every job she’s had was to quit and move on. She presumed she had bad luck or that “this is just how things are in the corporate world” … but never that she might actually be the common denominator of each and every circumstance.


I asked Candace, “What if you keep re-creating the same crappy work environment and the same terrible leadership in order to challenge you in some way?

What if, because you keep quitting before you’ve dealt with the real problem, you keep getting chances to step up?”

When we started digging deeper, it became clear that Candace kept attracting the same domineering bosses because she was frightened of standing up for herself.

She would often just cave to what everyone else around her expected, scrambling to meet unrealistic demands, because she was afraid of setting boundaries and directly communicating her needs.

So I asked Candace to start setting boundaries and directly communicating her desires to her boss now, before jumping ship and looking for new opportunities. It was scary … for about 5 minutes.

And then, it was awesome.

Because once you realize that I am the common denominator of this pattern, and that I have the responsibility for evolving past it, and that I can take action to change it … the pattern starts to dissolve, often very quickly.


Candace still wants to move on to a new job, and that’s fine. The reason she wants to move on is finally a good one. It’s not because she’s running away from a crappy boss, but because she’s moving toward a subject area that she’s actually interested in and inspired by.

And I’ll bet that Candace’s next boss will be a good one, too, because she no longer needs a domineering boss to challenge her. She can stand up and communicate for herself just fine now.

The same was true for me, and can be true for you, too.

When I answered “Why do I keep happening to this?” for myself, I realized that I kept manifesting the same low-paying, unfulfilling jobs because I didn’t really believe (at the time) that anything else was possible.

I assumed “this is all there is,” and my reality matched my assumption. For a long time, I blocked any career possibility beyond low-paying and unfulfilling jobs, because I presumed (incorrectly) that I couldn’t have anything better.


Maybe the dramatic romantic relationships are asking you to finally deal with your insecurities and feelings of self-worth.

Maybe every failed diet is pleading with you to realize that until you stop feeling ashamed of your body, nothing will change.

twitter-birdEvery old pattern that repeats itself is a question: “Will you choose to evolve, or not?”

Candace was being asked to stand up for herself and become the confident person that’s been there all along. I was being asked to think bigger about what was really possible for me and my career.

So, if every old pattern that shows up is really just an opportunity to evolve, then what are you being asked to do differently? Leave a comment to let us know!

Much Love,

Rachel (+ Kristen)

7 comments | add a comment | Share this > Tweet this > Email this >
  1. Why does this keep happening to me? I 100% relate to Candice. I’ve been in the same situation many times and now I am unemployed. I know its something I’m doing or not doing. I stood up in the wrong way and lost my job. How do I stop the cycle?

    1. Jeff — I think you stop the cycle by being willing to ask yourself, “OK, what have I not learned from this yet?” It sounds innocent enough, but it can be scary to ask ourselves that kind of question! There are a lot of clues to be found in the kind of pattern that shows up, too. If the same old characters or situation keeps happening, and you keep responding the same way … then what’s a VERY different way you could respond? Maybe even the OPPOSITE of how you’ve previously responded? (Not to say that doing the opposite is always the answer, I just think it’s a good way to get your mind thinking in a totally new gear!).

  2. I’m an executive coach and leadership development consultant in Toronto, and just want to tell both of you that your approach to coaching, your emails,and your topics are unique, refreshing, and very helpful to people. I wish you much success, which I’m sure is happening already. Well deserved.

    1. Thank you, Michael! That’s a great compliment that we’ll wholeheartedly accept. 🙂 Thank you for reading! We love connecting with other coaches!

  3. I am currently at my first full-time job but experiencing something I dealt with at my previous part-time job. I seem to be the only one who cares when work is done and that leads to my being overwhelmed. I’ve spoken to my employers multiple times but their assurances that things will change never seem to pan out.

    I don’t even like my job but I know things need to get done and I appear to be the only one who can manage to do it. Since this seems like a “good” thing, how can I change for future jobs so I don’t continue to be stuck in this horrible cycle?

    1. Gillian — I think the key to your answer is in your statement “I don’t even like my job.” BINGO! If you don’t like it, how do you think everyone else feels? I’d imagine most people are in the same boat as you! The only difference is that you’re the kind of person who still feels motivated to get the work done, even for a job they don’t enjoy. That’s admirable! Because, as you’re learning, most people who aren’t happy aren’t going to get anything done. They’ll be apathetic, unengaged, and positively terrible at getting anything done on time. So, the answer for you in the future? Be very conscious of joining a team that’s INSPIRED and energized by what they do! I promise that if you, and everyone you work with, really cares about their work and WANTS to be there, this problem will rarely show up. I know this is easier said than done, but perhaps this will be the motivation you need to find a position that inspires you, and where the team around you is as equally energetic about their work. It’s critical for morale and success, as you’re finding out now!

  4. I keep having this issue, but for me, it’s that the jobs have crazy people, impossible work situations, and abusive environments. They are situations wherein even objective bystanders have commented that I am being targeted/victimized, etc. I’ve been in therapy for years to deal with this, and even my therapist calls this a “cosmic joke,” because it continues to happen despite my becoming stronger and more assertive over the years. From my first jobs as a teen, babysitting and working in fast food up through now, it’s been sexual harassment, unsafe working conditions, being targeted to the point my boss was under investigation by others, and all manner of disorganization and dysfunction. Any advice would be welcome!

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