During the past several months, I’ve heard from scores of women and men who are experiencing deep challenges and even trauma in the aftermath of trusting the wrong people. Because they put their faith in these fakers, cheaters or emotionally unstable individuals, they’ve made big life and career mistakes and engaged in the wrong jobs, partnerships, relationships, deals and more.

When a particular challenge like this shows up in my coaching work at a higher frequency than usual, I know it’s something to pay attention to.

I’ve spent years working to understand why people do what they do – first, in my corporate career, then as a marriage and family therapist, and now as career coach and writer. In these cases, with my clients, we’ve looked closely at why they trusted people who led them astray. We’ve explored if they sensed it was a bad move before they did it, and why they fell for these individuals who lied, cheated, hurt them, or purposefully misrepresented themselves and the opportunities at hand.

In all cases, the reasons are similar. I’ve seen that there are five underlying reasons why we get duped continually by people we shouldn’t trust, and why we’re susceptible to chronically trusting untrustworthy people who, in the end, are out only for themselves and their own gain.

When I think back on one of the worst career decisions I ever made that generated serious trauma in my life, it was trusting the wrong person – a boss who was a very new hire at the company with little relevant industry experience – and believing what he said about the job that seemed to be the answer to all my prayers (money, influence, power, flexibility, etc.). Even before my first day there, I started to get all sorts of huge, worrisome signs that this would be a disaster. But I’d already accepted the role (for many of the reasons listed below). And I was too weak, insecure and afraid of the consequences to reverse my decision after accepting it.

The top five reasons that we trust the wrong people are:

1. We desperately want to believe them even though we know what they’re offering is too good to be true

When we’re in a situation that we desperately need or want to change, we often disregard all the outward and inward signs that indicate if a person should be trusted. Instead, we go with what sounds wonderful and impressive, and what we think will get us out of our current pain and challenge as quickly as possible. Even if we know what this person is offering feels too good to be true, we jump at it because we want to believe there’s a quick, easy way out of where we are today.

2. They validate what we need to believe about ourselves

Untrustworthy people with an agenda often know exactly what to say to us to get us hooked. They sense clearly (and scan for) what our “power gaps” are – where we’re lacking in confidence and self-esteem and what we long to believe about ourselves and our lives – and they tell us what we wish to hear. That makes us feel good so we follow them.

3. They appear as if they’re “winners” – they’re charismatic, persuasive and impressive

Narcissists (those with a true narcissistic personality disorder) and other emotional manipulators are often the people we trust when we shouldn’t. Why? Because they typically appear strong, confident, in control and highly successful. They seem to be “winners” in their own lives and careers, and we want some of that to rub off on us. And we feel good that these “winners” choose us to play on their team. But when we get to know them, or if we ever have to challenge what they say, think or believe, we’ll very soon see that they’re not safe or to be trusted, and they’re not at all what they appear to be.

4. They make us feel as if somebody finally recognizes our talents

In looking back on my life to date, I have to admit that I’ve trusted the wrong people when they made me feel as if I were finally being recognized and appreciated. They praised me for my talents and abilities, and talked about how I stood out from the competition, seemingly able to understand what I was all about and who I was at my core. And that made me feel understood, valued, and in good hands with this person.

Sadly, untrustworthy people will often hit you right in your Achilles heel, praising and puffing you up 

…so you feel terrific in their presence. But this type of flattery and praise is short-lived, and while it might feel great at the time, it’s simply a tactic to get us to like and follow them. It’s not heartfelt, and they can turn on you on a dime. It’s a manipulation play.

5. We hand over our power and skip the due diligence we need to do, to ensure this is a good move

Even though they’re about to engage in something very important with an individual, many people don’t conduct the necessary evaluation of the person before they just plunk down their trust in them.

If we look up “trustworthy” in the dictionary, we see these descriptions and synonyms:

  • Dependable
  • Able to be relied on to do or provide what is needed and is right
  • Solid
  • Secure
  • Safe
  • Responsible
  • Tried-and-true

How do you discover if someone is trustworthy?

There are some very reliable signs of trustworthiness (here are 15 that are helpful) in assessing their behavior, attitude, values and integrity that indicate if this individual is someone you can trust. Don’t go by just their words alone – investigate deeper. Words are cheap.

If trusting the wrong people is a chronic problem for you, you can change that. 

The first step is to stop in your tracks before you say “YES” to anything or anyone that involves a commitment on your part. 

Take some quiet time alone, and write down all the reasons you feel compelled to follow and trust this person, and all the signs and feelings you have that perhaps you shouldn’t.

Ask yourself these questions:

  • Does he or she remind me of someone in my past?
  • By trusting and following this person, am I trying to “fix” or heal a big a problem in my life in the shortest way possible?
  • Does this situation remind me of another situation that went wrong in my life?
  • Are there any outward signs that I should NOT trust this person?
  • Are there any behaviors (past or current) that raise a red flag about this person?
  • What do other people I trust share about this person’s demeanor, behavior and trustworthiness?
  • Do I have an intuition or sense about this person that I’m ignoring?
  • Do my mentors and advisors think it makes sense to trust this individual?
  • What are the potential outcomes in my life and career if I went with my gut and didn’t trust this person?

If you chronically trust the wrong people, the key is to slow down, conduct a thorough, balanced and unemotional assessment of this individual and this opportunity, and also ask for trusted outside input to effectively evaluate the best next step in your life.

Ideally, our internal guidance would be powerful and reliable enough to point us to the best people to engage with. But for many, they’ve been trained from their childhoods and pasts to not hear or heed the voice inside of them that is screaming “STOP!”

The ultimate step to a more successful life and career is to develop more courage, confidence, self-esteem and strength to sense clearly what your internal guidance is telling you, and to “find brave” to rise up, speak up and stand up strongly for what you want, for who you are, and for the great outcomes you richly deserve.

For hands-on help to build a more empowered future, work with Kathy, download her free e-guide A Surefire Plan To Figure Out What You Really Want and visit her Finding Brave video training library.


  • Kathy Caprino

    Hi! I’m a career and leadership coach, writer, and speaker dedicated to the advancement of women in business.

    Kathy Caprino, LLC

    Kathy Caprino, M.A. is an internationally-recognized career and leadership coach, writer, speaker and trainer dedicated to helping professional women  "find brave" and close their power gaps to create more success, fulfillment and reward in their lives and work. A former corporate Vice President, a trained marriage and family therapist, and the author of Breakdown, Breakthrough and the new book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss, Kathy is the Founder of Kathy Caprino, LLC and of the Amazing Career Project online career course and the Amazing Career Coach Certification training program. She is a Senior Contributor on Forbes.com and leading voice on Thrive Global and LinkedIn, and a top media source on careers, women’s issues, and leadership and has appeared in over 200 of the nation’s leading publications, and on national radio and TV. Her podcast Finding Brave ranks in the top 100 Apple Career Podcasts in the U.S. and beyond, and shares compelling interviews with top business and leadership experts, bestselling authors, creatives, entrepreneurs, and thought leaders who are making a brave difference with their work. For more information, visit KathyCaprino.com and FindingBrave.org, check out her new course The Most Powerful You, and connect with Kathy on LinkedIn, Twitter, Facebook and Instagram.