How do you help friends stop underestimating themselves professionally without being a prick?

I have a few good friends of mine who are smarter than me and more hardworking. We’re all in our late 30s / early 40s and two of them are married with children.

They are not broke (well, one of them almost is) but they all could use more income to buy homes or save for their kids colleges, etc. and as their friend, I feel I am slightly responsible for them not believing enough in their own talents.

However, I do not want to sound to my friends like a prick stealth bragging or condescending.

So, how have those of you who have felt this way handled it? It would be easiest for me to just say and do nothing, but it feels like the convenient, cowardly thing to do.

I think we need more specifics as to how they’re underestimating themselves or not believing in their own talents. Are they staying in low-paying jobs instead of seeking out a promotion or applying elsewhere? Not going back to school for an advanced degree that might help them advance? Presumably you feel that, whatever they should be doing differently, it would be prickish/bragging/condescending for you to advise it. Do you feel you have a good handle on why they haven’t done it already? Are you sure it’s just a lack of confidence?

None of them needs to go to college to get a degree. Some free online self-learning at the most.

A couple staying in low-ish paying jobs for a very long time with no proper raises (which they’d get if they applied elsewhere).

A couple have a lot of useful pharma/tech knowledge but are only working/applying for low end jobs that do not use their skills.

It’s definitely a lack of confidence, combined with a lack of free time though the lack of free time wouldn’t be as much of an issue if they believed the investment would be worth it.

And I get it. Only reason I got my current well-paying job is because I was let go, twice, and “demoted” once which led me to quit. All those times, I was forced to look for another job, which showed me I was underpaid. (I knew I was underpaid the first time, but not the second).

I think if my friends knew how borderline incompetent almost everybody is and how many are flying by the seat of their pants (as I have realized in the past couple of year of working with dozens or engineers at different Fortune 500 companies) they would do it.

I’m not even entirely sure how stealth bragging would play into this. Encourage them. Praise them. Offer them support. You can use your experience in the job market without sounding condescending or stealth bragging, but focus on them and their abilities and your belief in them. But it’s possible they’re just content where they’re at and don’t want to rock the boat. That can be frustrating to watch, but if they don’t seem the least bit interested in changing jobs or applying for promotions, I wouldn’t push it. Just be their friend and be supportive. But if they say something, “there’s this position that just opened up for work, but I don’t think I’m qualified for it” and you do think they’re qualified, gently encourage them. Tell them it’s understandable to be trepidatious about a new job/position, but you believe they are qualified for it and it’s worth at least trying. The worst that happens is they don’t get the job, but they might rack up some interview experience or job hunting experience that will help them in future applications. But I wouldn’t push it too far. It’s their life.

Not everyone is a “Type A” personality.

I personally don’t think that someone who isn’t driven by nature can learn to be, or someone who isn’t can learn to relax. It is like forcing someone who is left-handed to use their right. Myself, I’ve never had drive, and I’ve never been able to make myself have drive. And it isn’t because I’m “underestimating myself”, it is because being driven is alien to my very nature. I am congenitally without fucks to give.

First thing is to not compare them to yourself to gauge their level of success / happiness. That is measured within ones self.
People have various ways and degrees that they wish to interact with the world. Yes some can just be lazy. But many have a more complex way of it. Even people with a good estimate of their abilities, may have personal issues with presenting and using those abilities to get ahead. They just are not comfortable with pushing themselves onto others to get ahead or even noticed.
It can be very complicated as to why a person with good abilities does not push them out there.
As a friend who cares to help them grow. Take every opportunity to let them know about how much they have to offer. Not pushing them. But noticing and noting to them, their pluses. In everyday stuff. In more direct work related stuff. Not, you should do this. But, you could do this. You can subtly build their confidence. Workplaces are often competitive. Many people with great skills, just don’t like to pit themselves in competition. Preferring to be just discovered.
As their friend. Keep discovering and telling them their skills. But don’t push them to do something uncomfortable. Try and get them to build up their expectations of themselves. Be sneaky.

Your friends are not unusual. I know people who have worked as cashiers at Walmart for 10+ years.

I have made something of a minor hobby over the years of observing people, and one of the things that I’ve discovered is this – some people are just plain not interested in advancement. Another thing that I’ve discovered is that others are actually afraid of taking on responsibility. They practically beg for somebody else to make all the major decisions at work.

Why? You’re not their parent (and even if you were, they’re presumably adult enough to be responsible for their own lives).

By all means, say encouraging things from time to time, especially if they ask, but unless they’re really unhappy with their job or anything else in their life, it’s their business, surely?

I don’t get a clear sense of how much your friends regret their circumstances. If they’re expressing dismay and undeserved self doubt, it’s very much good friend behavior to tell them what you see in them. I have a couple of friends who are like that – they’re quite good and sometimes sell themselves short only because they’ve been trained to, and they express some frustration. There’s nothing prickish about telling people the good you see in them, if you’re not also basing it on a presumption that you know this because of your own superiority.

But, like others have asked, what do they actually want?

It’s always good to truthfully say, “I really admire/appreciate/respect the way you did…” or “…the way you can…”. But the circumstances in which you can helpfully go on to imply that they can turn around their history of wasting their careers and screwing up are much more rare.

And it’s important for the OP to note, there’s nothing wrong with that. Their goals and aspirations need not coincide with one’s own, and their happiness or contentment may not be tied to those things. There’s something to be said for a lifestyle that is comfortable enough, but doesn’t have the stresses and responsibilities of more financially/professionally “rewarding” ones. Like I said above, if they show interest, be encouraging, positive, and supportive. If they don’t, they may very well be fine where they’re at, and don’t stress them out with what you think they should be doing. They are not you.

Exactly this, one man’s “lack of drive” is another man’s “content with what you have”.
It is only an issue if they are unhappy with their lot.

It’s complicated, though. I have a friend who has never make above $35k in her life–she’s 45. She has a college degree. She’s smart and reliable. But she just really seems to see herself as destined to be an assistant manager in retail. I think she’s say she’s happy with her life, but she’s also having to put off really important dental work because she can’t afford it and making other lifestyle compromises that are mind-boggling to me. But when she was recently laid off from a job after 10 exemplary years (store closed), she absolutely assumed that meant she’d have to find a similar position and start with a pay cut because in her mind, you get a shitty retail job and work your way up. She wouldn’t even look at jobs that paid real money (like, over $40k/year) or were vaguely professional, because in her mind, she just can’t see herself making that kind of money. It’s just not who she is.

I get that it’s her life. But when this intelligent, hardworking, capable woman is talking about teeth rotting out of her mouth because she can’t afford to fix them, it’s very hard not to shake her and tell her to aim higher. We’ve been friends since middle school and she’s always been this way.

I honestly don’t know if she realizes how much the rest of her college friends make. Like, maybe she knows that we do better than her, but that we make like $45-50k, not twice that or more. It’s not like we talk about it. So I wonder sometimes if she’d be more willing to try for those roles if she saw that the same dorks she went to middle school with, that she knows she’s a “good” as, have so much more financial security than she does.

It’s not my business, and I know that, but it’s hard sometimes, even if it’s a snobby thing to struggle with.

Ask if they are interested in getting ahead. If they say yes, tell them this (true) story.

One person felt very frustrated and unappreciated because no matter how hard they worked they were not getting ahead. Then they mentioned this to their boss. The boss said “Is that what you want? I never knew. We’re looking for people to put on the advancement track. I’ll put your name in.”

In a few years, the person was jumped up a few levels.

Sometimes, the greatest difficulty is just deciding what you want and asking for it.

My 2 cents is, do your friends consider their income and work to be an acceptable life-work balance, maybe even ideal?

For instance, I’ve worked a job at a company over the past 11 years that pays modestly but is remote, low-stress and has good bosses. For someone like me, that’s an ideal setup and I have little desire to change it. My siblings, who are go-getter Type A types, have prodded me before to make more money and be more ambitious in climbing the career ladder - my sister has on many occasions urged me to hop to some other job - but - I’m happy as is. I don’t want to increase my salary by 30% in return for a 70% increase in stress and hassle.

My siblings probably think I’m “underestimating myself professionally,” as the OP thread title states, but it’s not that I am, it’s that I’m already happy where I am. It’s the ideal X-Y intersection on the axis chart for me.

If they are happy and/or not complaining about their lots in life, should you even be concerned with this?

I think that being self-aware in this way is a good thing and I also appreciate that you are seeing material harm being done to someone you care about and which is fully in their power to change.

I can see the conflict and potential frustration. Who wouldn’t want their friends to be happier and healthier?

My recommendation to Gozu is to spend a little time examining why you feel the need to “fix” them. Is there something you are not getting out of the relationships because of their circumstances? Speaking for myself, I have had friends in the past that I no longer spend time with because we ended up in vastly different economic lifestyles. I would have enjoyed doing things together, but they weren’t in the same place financially. Could that be part of your motivator?

It is certainly admirable to want to help people, but as you seem to be sensitive to, there are potential pitfalls involved. Maybe explain to them that you feel this way and you are struggling with it (phrased as something about you, rather then something about them.) They may be able to provide their perspective in a way that guides you better.

You hit the nail on the head. I think that your theory is 100% right and that it is absolutely vital most of us have people to compare ourselves to to change our self-worth. Here is an example :

My SO, Gozua, was onboarded with 2 other junior developers (let’s call’em Alice and Bob) at the same time. They worked a lot together so they knew each other’s strengths and abilities.

Alice, left 8 months later for a job paying 50% more. Awe-inspiring career move.

Gozua, whose plan was to stay at her first job at LEAST one year, and who was completely satisfied with her salary until then, told me she knows she’s a better developer than Alice, so she updated her resume and started interviewing. If Alice was worth that much, then surely she was too. Can’t argue with that logic!

After failing a few technical interviews, Gozua received and accepted an offer for 60% more of her original salary (+RSUs) , and now she makes more money than Alice and is exceedingly satisfied with her generous compensation. None of this would have happened without Alice leading the way. (bless you Alice!)

Another example:

I used to think I was worth half of what I make now. I was not thrilled at the 2% raises year over year but I thought that’s what I deserved for not overworking myself and prioritizing my personal life and health.

I fortunately got laid off because the company was losing money and then received offers of 50-60% more. Only then did I realize I had been underpaid for half my tenure there! The parent company was losing money the whole time and that’s why they were not very generous.

I could’ve been paying a house mortgage with the salary difference over those 3 years. I should’ve job hunted after 2-3 years instead of waiting 6 years to be forced to. I would have bought a house right before prices skyrocketed too. Stupid, stupid me!

So that’s where I’m coming from. From a place of humility and stupidity. And I see people making the same mistakes I made, so I must assume that lots of people are in this situation of underestimating their fair market value.

I cannot deny that It is, indeed, partly because I selfishly want them to have more money for plane tickets to come visit me. Most of my friends live thousands of miles away, in other continents or states.

Partly it is because I wish someone had shaken me by the shoulders years before I was laid off.

Partly, it is because I want them to retire at a decent age so we can spend some quality golden years together in a decade or two. Before the world turns into Venus.

Partly, it is because I know that those decades-old friends are good folks and deserve better than being stressed out about money. Financial stress can cause all sort of badness, like divorces that would have been avoided if money were plentiful for things like child care or plain old bills. Some of you have probably have also seen this first hand.

Have these underpaid friends of yours heard this story?

It may be that they’re in the same position as you were, and would benefit from hearing about your experience. It may be that their circumstances are different, and even if they’re every bit as smart and talented as you are, they’re already trapped under a salary ceiling in their field, and don’t want to completely change careers. It may be that they have looked into their options and decided they are satisfied with where they are, or that the trade-offs are worth it even if it would be nice to earn more.

Do they complain to you about their financial struggles? I don’t mean in the sense of saying “sorry, I can’t afford to fly out and visit you;” I mean explicitly lamenting not making more. If they do, I think that’s a valid opening to say something like, “you know, I think you’re worth a lot more than they pay you, and I bet you could earn a lot more at another company.” If they express interest, even with skepticism, you could offer your story. If they start telling you why you’re wrong, or shrug it off in a non-committal way, let it go.