In a previous article, I explored how to avoid signing up for the same bad work experience again. Part of that conversation was acknowledging that sometimes we see a warning and still choose the opportunity for a very real and valid reason in life.
Today, I want to go a little deeper into that decision.
What made a particular red flag easier to ignore? What did the opportunity represent? And is there a pattern in the things you tend to overlook?
This is a reflection exercise. Take a piece of paper, open a note on your phone, or use whatever helps you get the thoughts out of your head and somewhere you can examine them.
It’s time, once again, to externalize!!
What was I hoping this opportunity would give me?
Start with a job, promotion, or internal move that you felt hopeful about but that became a pretty big disappointment. Either because it wasn’t what you thought or it didn’t change your working conditions the way you hoped.
Before you list everything that went wrong, ask yourself: Why was I hopeful?
Then make two columns:
- What was I running toward?
- What was I running away from?
These questions can sound similar, but they tell you different things about the decision.
Perhaps you were moving toward work you wanted to learn, an opportunity to lead, or more income. Perhaps you were moving away from constant evening work, a manager who belittled you, or pressure that had become difficult to live with.
Make the examples specific. “A better job” does not tell you as much as “a role where I could spend more time solving problems and less time defending every decision.”
Try not to fill the columns with the same observation reversed. “I wanted to leave a toxic manager” and “I wanted a better manager” may describe the same motivation.
Which was stronger for you at the time: the push to get away or the pull toward something particular? Put that observation in the column that best reflects your experience, then look for other distinct reasons.
Was I chasing an opportunity or relief?
Your columns do not need to be equally long.
You might discover that you can name ten things you were trying to escape but very little about what you wanted from the next role beyond being somewhere else.
That alone can be very telling into whether we were moving towards something better or away from something painful. The emotional intensity behind each item is important. One reason to leave may have carried much more weight than several reasons to join.
The length of a list alone does not tell the whole story, it never does, but the ultimate question is “what was driving you?”
In my experience, when the decision is mainly about getting relief from an existing situation, it can become easier to overlook concerns about the next one. We want the new opportunity to be the way out, so much so, that we’ll ignore the 100 red flags during the interview process.
That does not make wanting relief wrong. If a manager is belittling you or work is consuming your evenings, wanting distance from that is understandable.
And recognizing how much relief mattered can help explain why you accepted an answer, skipped a question, or minimized something you would otherwise have investigated.
What was actually said, and what did I hope it meant?
Now return to the conversations you had before accepting.
For a promotion, what did your boss say would change? Did you discuss responsibilities, authority, support, or how your existing work would be handled? Or did you assume those things would change because the title was changing?
For a new job, how did you investigate the environment? Did you ask the manager questions about how the team worked? What did they actually tell you?
Write down what you remember being said. Beside it, write what you took it to mean.
For example, a manager might have said, “You’ll have more ownership in this role.” You may have heard that as a promise of more decision-making authority and less oversight. But did you clarify what ownership meant to them?
That difference is important, because it could have also meant that you are going to be responsible for everything that flies the team’s way.
This part can be difficult without notes or a recording, being able to recall the exact conversation. If you have emails or notes, you can use them to check your recollection.
Did you have the facts, or did you think you had the facts?
You may find that someone made a clear commitment and did not follow through. That is different from discovering you attached a meaning to something that was never clarified. Both can lead to disappointment, but they point to different problems.
Also… be very careful about the “spoken promises” that were never put down into writing. They usually look like “Don’t worry, we’ll make sure you get taken care of”
What happens when I compare several decisions?
Once you have worked through one situation, repeat the exercise for another, and then at least one more. Aim for at least three situations.
For each one, look at what you were running toward, what you were running from, and the gap between what was said and what you hoped it meant.
Then look for common threads.
Do you repeatedly interpret vague language as a specific promise? Do you avoid asking follow-up questions when you are excited? Do you assume support will come with a promotion without discussing it? Does the need to escape make any alternative seem good enough?
These are what I would call your blank spots: the parts of a decision that you are more prone to leave unexplored.
You are looking for a pattern you can name clearly. “I make bad decisions” gives you very little to work with compared to… “When I need relief, I stop asking about the conditions that exhausted me in the first place” which gives you something specific to prepare for.
If a pattern is not clear yet, leave room for that. There is no need to force every experience into the same explanation.
How can I use that pattern next time?
Once you know where you tend to leave gaps, you can prepare questions and actions that address them.
If you tend to read more into a manager’s words than they said, ask them to describe what those words mean in practice. If you assume a promotion includes support, ask what support is committed and when it will be available.
If relief drove several past decisions, keep your reasons for leaving visible alongside what you have actually learned about the new opportunity. Being different from your current job does not yet tell you how it will be different.
And give yourself room to ask a larger question: What am I chasing, and why am I chasing it?
You may still decide to take an imperfect opportunity. The point is to understand the choice you are making, including what remains uncertain.
Knowing your blank spots gives you something to prepare for. The next time a familiar warning appears, you have a better chance of pausing, asking the question you previously skipped, and deciding with more of the picture in view.
Common blank spot signals
And if at the end of this exercise you’re still unsure, here are some things someone might say during an interview process that should be “red flags.”
- “We’re like a family here.” Especially when it came up while explaining late nights, personal sacrifices, or expectations of loyalty.
- They were vague about working hours. You asked about evenings or weekends and heard, “We do whatever it takes.”
- They couldn’t explain why the previous person left. Or they blamed that person without acknowledging anything about the workload, support, or expectations.
- Several people had recently left the team. You noticed the turnover, but accepted “They weren’t the right fit” without asking more.
- Different interviewers described different jobs. The responsibilities, priorities, or measures of success changed depending on whom you asked.
- Everything sounded urgent. They needed someone to “hit the ground running,” but couldn’t describe onboarding, training, or support.
- The manager couldn’t explain how they handle competing priorities. Their answer was essentially that good employees find a way to get everything done.
- They promised that things would improve after you joined. More staffing, better processes, or a lighter workload were always coming “soon,” without anything concrete behind them.
- Career growth sounded exciting but undefined. They mentioned advancement opportunities, but couldn’t give an example of how someone on the team had actually progressed.
- They advertised autonomy while describing constant approval requirements. You would supposedly “own” the work, but have little authority to make decisions.
- They spoke dismissively about employees or other teams. You heard someone described as difficult, overly sensitive, lazy, or unable to handle pressure.
- They treated your questions as a problem. Asking about workload, flexibility, compensation, or management support seemed to make them defensive.
- The interview process showed little respect for your time. Repeated cancellations, unexplained delays, or substantial unpaid assignments kept getting excused as a busy period.
- They pressured you to accept quickly. You were discouraged from taking time to consider the offer or get important questions answered.
- What employees said didn’t match what leadership promised. The manager described flexibility, but team members casually mentioned working most evenings.
- You noticed a familiar warning and explained it away. “My last boss said that too, but this person probably means something different.”
