
25Y Male making over $250K+ annually. Still stuck. Help? - frankphilips
My friend is a 25Y old male with a wife and a newborn. He has a high paying salary (Over $160K+ annually), and his wife makes over $90K. His schedule is pretty flexible, and he enjoys his job although he hates his commute. They aren&#x27;t a showy family.  They both drive used cars, cook at home, max out their 401K, etc. However, my friend still feels &quot;stuck&quot;. Like he hasn&#x27;t accomplished what he was called to do in life. He&#x27;s always working on some startup trying to become the next millionaire but continues to fail. What kind of advice can I give him?
======
davidu
He doesn't understand how to be happy or satisfied. He needs a therapist. I
think most people do, they underestimate the value of having an independent
sounding board to help work through these kinds of feelings.

His expectations are either unrealistic, or he's surrounded by people who are
always doing better, despite him doing well, which makes him seem like a
failure. He has the luxury of those feelings.

Silicon Valley can be a totally distorted place where there is always someone
doing better. It's important to look inwards for satisfaction, and not
externally, or some arbitrary barometer of success.

Plus, the people around him who appear to be winners, are often chock full of
their own problems.

~~~
thirdtruck
Agreed. I look forward to the day when twice-yearly visits to a therapist are
as socially-accepted and -expected as visits to the dentist.

Your brain, like your teeth or your car, needs regular servicing by a
professional if you want optimal performance and want to avoid costly repairs.

~~~
jdbernard
> Your brain, like your teeth or your car, needs regular servicing by a
> professional if you want optimal performance and want to avoid costly
> repairs.

I don't know that I agree. I was fortunate to be raised by incredible parents.
I emerged extremely well-adjusted and prepared for adulthood. I am not saying
I never benefit from a counselor or therapist. There have been times I have
visited each for help and advice, or even just to get an outside evaluation
about something. But I do not need to go regularly like I would to the
dentist. That's not being arrogant, that's just knowing myself.

Your brain needs regular exercise, sure. But I think it is more analogous to
physical exercise than something like the dentist. I agree that most people
could benefit from having a regular appointment with a physical trainer, but
many people are well-equipped to be their own trainer, at least for the
purpose of staying healthy and happy. I think the same is true of mental
health.

~~~
thirdtruck
I think we agree in the large part. The part about relying on a third-party
professional was assumed.

I'm reminded of a relative's teeth: they might have been born with exceptional
enamel, preventing all manner of early cavities, but now they lack the oral
hygiene habits they need going forward.

Along those same lines: to what degree are you uncommonly well-adjusted,
versus born to circumstances in which many of your foibles don't cause
problems to _you_ because of the consequence buffer provided by fortuitous
race, sex, orientation, class, etc.? I know I can get away with under-
developed stress processing because I'm white and male and date women, for
example.

~~~
jdbernard
Well, I can't claim to know with absolute certainty how I would react in
situations that I have never been in; I am not omniscient. I do feel like I am
fairly well equipped to handle whatever situation was given to me without
regular help from a therapist.

I'm not saying I'm perfect, far from it. But I am well aware of my faults and
fairly well aware of what I would need to do to shore them up. That doesn't
mean it is easy. Like I said, I don't have any problem going to a therapist
for help with something I am struggling with. But I can't imagine any
situation in life where I would need to regularly visit a therapist.

Like your relative, I was gifted with great genes as far as my dental health
goes. I've never had a cavity or any oral problems for that matter. Somewhere
along the way I learned to take care of my teeth properly. However, I still
need and benefit from regularly visiting a dentist, despite my good genes or
how well equipped I am to handle my teeth on my own. I just don't feel the
same about therapists, as wonderful as they can be.

------
austenallred
Honestly, have him read "Walden" by Thoreau. Here are a few of my Kindle
highlights.

"I was more independent than any farmer in Concord, for I was not anchored to
a house or farm, but could follow the bent of my genius, which is a very
crooked one, every moment."

"This spending of the best part of one's life earning money in order to enjoy
a questionable liberty during the least valuable part of it reminds me of the
Englishman who went to India to make a fortune first, in order that he might
return to England and live the life of a poet. He should have gone up garret
at once."

"Most men, even in this comparatively free country, through mere ignorance and
mistake, are so occupied with the factitious cares and superfluously coarse
labors of life that its finer fruits cannot be plucked by them."

"I sometimes wonder that we can be so frivolous, I may almost say, as to
attend to the gross but somewhat foreign form of servitude called Negro
Slavery, there are so many keen and subtle masters that enslave both North and
South."

------
zoba
I deal with this concern myself, and the answer I've been mulling over
recently is related to the Big Fish In A Small Pond analogy. (In fact, I think
of it in the same terms as your friend: winning my freedom)

In the Bay Area, things are very expensive and its hard to put money away, and
its also hard to feel like "you've won" because other folks are so
dramatically more successful than you. However, after visiting home for
Christmas I realized that I'm actually quite successful. So the problem is
that I'm a small or medium fish in a very large pond. So I don't ever feel
like I'm free because I'm not a big fish. Whats unfair is that a lot of the
big fish in SF owe their size to luck. Its not that they are necessarily
objectively better than the smaller fish, they just got lucky. (Granted,
sometimes they are better: Elon Musk).

So, my advice to your friend would be to seek a high paying job which allows
telecommuting, for both him and his wife. Then, move to somewhere livable but
dirt cheap. Then, sock money away like a madman. Then, once you've got a pile
of cash...stop working. Stop working for 3 years or so, enjoy that 3 years of
freedom. Build something, maybe it will take off.

Thats where my thoughts are right now, it'd be great to hear an update on what
he thinks about it.

EDIT: I wanted to add this follow up. One of the interesting things about this
conundrum is, for me, not being as successful/free as I want creates a
significant amount of stress. I worry about it far more than I should. I worry
about it to the point where it has a negative impact on my ability to think
clearly because my mood is so depressed...and its like being stuck in a trap
because I worry I'm not successful enough, but the worry depresses me enough
that I can't pursue means of being successful. Its now a question of: Can I
overcome that stress in my current situation, or, are things going to have to
change?

~~~
ericingram
> Stop working for 3 years or so, enjoy that 3 years of freedom. Build
> something, maybe it will take off.

The more cash and runway you have to build something, the more cash and runway
you'll use. This is not necessarily a good thing. It could lead to over-
engineering, a feeling of security which keeps you from talking to users early
enough, and just a lot of potential for wasting time and money in quantities
you would otherwise not be comfortable with.

If you spend 3 years time and all of your savings and don't succeed, you may
become further depressed and your project derailed.

FWIW, I'd suggest starting a project on the side and continuing to make
incremental progress. It's hard, and doesn't always feel good, but the
pressure and lack of time will push you to make things happen faster and get
creative.

------
tomrod
There are a number of things to consider. Finding accomplishment in life is
something many struggle with.

Perhaps your friend would feel some accomplishment by:

* Mentoring new startups

* Mentoring disadvantaged youth

* Religion

* Community service/projects

* Becoming involved in local government service

* Horticulture

* Woodwork/old car restoration/old computer restoration

* Adopt an elderly neighbor as a "grandparent", that he goes and speaks with on a regular (at least weekly) basis

* Read the works of the greats, genre open

* Pick up painting or other artistic ventures

* Set a goal that's a lot of fun. For example, I know of a friend who has a life goal to hike each US state's highest peak or point. He's made it about 15 in, and has a lot left to go.

* Get involved with the local Boy Scouts/Girl Scouts program (related to mentoring), if Boy Scouts go through Woodbadge (extensive leadership training)

* Join a nonprofit board

Each of these points are kind of getting at a main point: live for something.
Work and career are certainly intended to be a vocation, but they aren't
always going to be an avocation. When avocation and vocation conflict, I
believe a lot of people get dissatisfied.

Of course, I could also be completely wrong and a therapist is advisable. But
it's something to consider.

~~~
briandw
Religion: How is a faith system i.e. "pretending to know things that you don't
know" going to help? Community is a good thing, sure. But how does faith help?

~~~
jstelly
Your definition of faith is incorrect. Faith in anything (religious or not) is
merely choosing to believe in it without the necessary evidence or facts that
would prove it to be true. "Pretending to know" implies something fairly
different.

I'm not sure I would recommend religion to this person. But I wouldn't be
surprised if his unhappiness comes from what he chooses to believe in some
context.

~~~
tomrod
I'm not arguing that this is the only nor optimal solution, certainly. Nor
that he should adopt or adhere to something he doesn't believe. I mention this
simply to note that many in the stage of life where they're discontent and are
"soul-searching" find solace and meaning in religion.

In short, it's an option that's there.

------
Haul4ss
Quarter-life crisis. He's asking "is this all there is?"

Not everybody feels compelled to a higher calling. In fact, I'd say most
people don't. That doesn't mean life isn't worth living, it just means he
hasn't found something that he can pour all of his extra energy in to.

Edited to add: Trevor Blackwell used to have something on his web site about
founder's stories. I can't find it now. Basically, he was saying that people
want to hear inspiring stories from founders about their "a ha" moments and
how they were driven to a single goal. This is not how it works for most
people. Most innovators, through hard work or happenstance, stumble upon
something they have a knack for, and pursue it until they slowly, gradually
push the boundaries of the possible. But that doesn't make for a good story.

------
USNetizen
Tell him to stop chasing the money. Save it up, get (or create, i.e.
freelance) a lower-paying position with more flexibility, live simply and
enjoy time with your family. No one ever said they wished they had spent more
time at work when they have children at home.

I wish I had followed that advice at 25.

------
quaffapint
Just let him know that I'm nearly twice his age, make half as much, fail at
startup ideas and feel stuck, as well. That should make him happier.

------
epipsychidion
What kind of job pays a 25 year old 160k with flexible hours? Genuinely
curious.

~~~
potatolicious
Many intermediate-senior level dev jobs at AAA-level shops (see: Google,
Facebook, etc), as well as many startups. I know people in this range (and
above) in both the Bay Area and NYC.

~~~
epipsychidion
Yes but at 25? That's 4 years of experience out of college. I'm in my second
year working in technology for a large i-bank and I'm barely breaching 100k :(

~~~
n00b101
I know this doesn't need saying ... But I can guarantee you that there are ~25
year old bankers at the investment bank who are making more a lot more than
$100k. Technology roles are discounted at investment banks, since they
perceive technology as a cost centre, not a profit centre. But at
Google/Apple/etc, it's the opposite - technology is a profit centre, and
finance roles are a cost centre.

~~~
epipsychidion
Yeah I understand that, I'm just surprised that it's feasible to make that
much in technology. I had an offer from Microsoft when I graduated that was
about the same so I'd have to gain around 14.5% every year to get to 165k.
Seems a bit high or perhaps I was just being lowballed.

~~~
potatolicious
Big companies _suck_ at giving raises. I've achieved a pretty decent average-
raise-per-year by hopping every year or two (works out to about 13% per year
for me), I've only been in the industry for ~4 years.

Experience is worth a tremendous amount in this industry, but you'd never
realize this if you're too loyal to a single employer. Shop around, hop when
it benefits you.

Most starting new-grad packages are around $100K these days in the Bay Area,
and said companies would be content giving you 1% to 3% raises a year from
there. To maximize your value you _must_ change jobs.

~~~
nicholas73
Is this really true outside of FB, Google, etc?

Outside of mobile/web dev?

------
rthomas6
Maybe this will help:

[http://www.mrmoneymustache.com/2011/10/02/what-is-
stoicism-a...](http://www.mrmoneymustache.com/2011/10/02/what-is-stoicism-and-
how-can-it-turn-your-life-to-solid-gold/)

------
codex
Does he live in SV? The culture of SV is the rat race with a small but showy
percentage breaking free.

~~~
tostitos1979
"Nice house for 250K"

No way is this SV.

------
PaulRobinson
When you earn a decent wage, most people assume you're set for life, however
you're not. In fact, it can cause problems that most people can't perceive.

Firstly, you tend to live within your salary terms: you get a nice home, you
spend a little more on the luxuries of life and you find each month that you
don't have quite as much left over as you would expect.

You don't need to be showy for this to happen. I know people on equivalent
salaries who don't own cars and live in small flats who don't have a lot of
spare cash.

And then you have the freedom aspect of things that ties in with this: because
you are never really sitting on a big pile of cash, and because the bills are
coming in regularly you feel trapped. You need to keep on making a decent
amount of money, and therefore you end up working for somebody else on
something you're not too happy with in order to just stay where you are.
Meanwhile, the industry moves on and you feel as though you're stuck in the
same place and eventually you'll get eclipsed, so you throw yourself into
staying ahead and all you're doing is running on a conveyor belt.

There's no easy fix. What I suggest for your friend is to focus on that
concept of freedom.

There is a metaphorical story for your friend about a tramp and a greedy
millionaire. The tramp proclaimed that he was the richer man because he had
all the money he wanted, yet the millionaire was compelled to keep working
because he wanted more. Who was the freer?

Live on less. Stockpile the cash. Realise you can buy a home outright with a
few year's savings and be free of rent or mortgage. Move and keep stockpiling
the cash. Grow food. Do more with less. Realise over time that you're spending
virtually nothing and you can live on that stockpile for 5 years. Then 10
years. Then 20 years. Then realise you're free. Stop working for somebody
else. Throw yourself into something you love.

I've been in a similar position to your friend - the only way out
realistically is to live on less. Chasing more is a fool's errand as a first
step. Make do with nothing, spend your time on something you love, and then
the opportunity will arise to have the freedom to do something more.

This idea that you can become a millionaire by writing some apps or mining
some Bitcoin is one of the most toxic and acidic things in our (development)
culture right now.

~~~
frankphilips
Paul,

I think this is where he fits in. When him and his wife were making only 40K
combined, they carpooled to work, lived in a 700sqft apartment, barely went
out, etc. Now that they got some money, they bought a decent house ($250K), 2
cars, and they started paying off loans etc. He said even though they make
$250K, his monthly expenses are over $7-8K. His whole thing is that he wants
to be "financially free". I think his business ideas all are focused on MAKING
MONEY, hence why he keeps failing.

~~~
User8712
At first I thought maybe work didn't seem fulfilling, and he wanted to run his
own business. Running a business can be extremely rewarding, so I thought this
was his plan. However, if he's only after money, then he might just be chasing
a pipe dream.

If he's making millions, he'll probably be buying exotic cars, and feel like a
failure because he can't buy a yacht. Then he makes tens of millions, has his
new toy yacht, but feels like a failure because he doesn't own a private jet.

With his current income, he should be able to live quite well. You said, he
wants to be _financially free_. If that's his goal, why is he racking up $8k
in monthly expenses? It seems like he wants to live a lavish lifestyle, that's
always above his means.

------
jackgavigan
Freedom comes from within.

Your friend's young. He has plenty of time to accomplish everything he wants
to (and what he wants to accomplish will change over time). Freedom comes from
within. It's important that he realises that he's already enjoying his freedom
to have a stable and settled life, start a family and invest in its future by
buying a house and growing his 401k.

Maybe he needs to start putting a little money by every month towards a
sabbatical fund so that, a few years down the line, he can afford to take 6 or
12 months off work and do the stuff he doesn't feel free to do now.

------
minimaxir
"High paying salary" and "continues to fail" are contradictions and very
unusual.

~~~
austenallred
That depends on your definition of success.

At a certain level how much money you make doesn't really increase our
happiness ([http://blogs.wsj.com/wealth/2010/09/07/the-perfect-salary-
fo...](http://blogs.wsj.com/wealth/2010/09/07/the-perfect-salary-for-
happiness-75000-a-year/)). It's tough, without knowing him, to know what his
real goals and desires are, but it seems to me like "make more money" isn't
the answer.

~~~
frankphilips
He always talks about how he wants to be "free". And he's not "free" yet. Even
though he makes money, he still has debt (school loans, mortgage, car
payments, daycare, etc etc)..

~~~
tostitos1979
I'm surprised no one here has said it yet. But your friend is actually quite
smart. While he and his wife are making 250K now, there is no guarantee they
will be making this much in 10 years. My wife and I had pretty high student
loans ... we are doing a somewhat decent job getting these paid off. Sadly,
because of all the debt, our net worth is pretty low even though we are in our
30s. Unlike your friend who is lucky/smart enough to earn such a high salary
in a place where a decent house costs 250K, my wife and I would need just
under a million to get a decent house.

tldr. 250K isn't that much these days when you factor taxes, child care,
housing costs and student loan replayments.

------
joshbaptiste
I don't get this rush to have a full blown family in your early/mid twenties.
I was terrified of having children in my twenties and just enjoyed travelling
and hanging out with friends and not be tied down with such responsibilities.
Now in my mid thirties I don't have this void feeling inside and ready for
whatever my current long term relationship brings about.

~~~
User8712
Same, spent most of my twenties enjoying the world, and focusing on business.
I wouldn't do it any other way, while a lot of my friends are tied down with
houses and families in their twenties.

I'm jealous of one thing though. They got to spend their twenties with the
partner they'll spend the rest of their life with. I've had a lot of great
times in my 20s, but those memories are mostly with people that have come and
gone. If you're meeting someone and starting a family in your thirties, it
needs to move quickly, and women always want to have children before 35. So,
if you meet someone early thirties, you're spending a quick year or two
together, and starting a family. If you meet early twenties, you could spend
at least a decade growing and experiencing a lot together before starting a
family.

So, that's my one regret, I'll never be a 40 or 50 year old, being able to
reminisce with my partner about the fun adventures we had together in our 20s.

However, you can't have it both ways, and I imagine people that settle down or
start a long term relationship early feel like they missed out on a few years
of independent freedom.

------
blahwoop
Nothing wrong with staying hungry in his professional life. At his age, no
matter how successful you are, you should always try to reach the next level.
As long as he is happy with other parts of his life i.e family. Nobody should
be satisfied with their career/life at age 25 but he has the luxury to balance
it with what his household income is at the moment.

------
nickler
He's stuck in the success trap. You've detailed a list that has very little
actual correlation to fulfillment. Those are all issues related to security,
comfort, and a lifelong desire to one day avoid work.

I wrote a couple pieces on this at startupathlete.com.

Protip: millions of $ =/= success. Ask any millionaire what they would wish
for and it's not another million $.

That being said, one of the best questions to ask when someone is in a rut is,
'if money was no object, if you had millions in the bank, what would you be
doing'. The follow up, 'why aren't you doing that', will always have some
excuse about money, which is bullshit. It's about fear, security, and risk
tolerance.

The happiest people I know have the stones to risk their pride, lose all their
stuff, and live with mistakes. The saddest people I know spend their later
lives regretting the risks they never took.

Wish you both the best of luck.

------
garyfirestorm
I think, in his situation, he is doing his best. Not a lot of people earn so
much money. Not a lot of people's wives earn so much. I think he deserves a
credit for trying. And after some amount of efforts he will get there. I have
witnessed a lot of criticism about the 'founder - millionaire goal of life'.
People who criticize such goals, I believe do not have big dreams, or for some
reason, they can't do it. Your friend should feel satisfied. Me being a recent
grad, earning about half as your friend, fail to even give it a try. That
should be considered as stuck. I think, through his attempts, a. he will learn
a lot. b. someday, he will get there. Goals should be decided by an
individual, you can't decide his goals, or can't call him stupid for chasing
million dollars. I guess that answers the question.

------
joebo
Just wait until the newborn gets a little older. I have two kids under 3 and
found a renewed sense of purpose as they've gotten past the newborn stage. My
priorities have also shifted away from career and startup success to family.
Perhaps it will be the same for him.

------
michaelrhansen
In life you have to find your own rules, values, and rewards. I find letting
anyone dictate that for you will make you miserable. Most successful startups
aren't done to be the next big millionaire, but b/c they felt compelled to
create something awesome.

------
hariis
What he needs is the "big picture".

This can be acquired in several ways, depending on the personality of the
person, from what I have seen.

So a few different things:

Recently, I saw a good talk by MindValley CEO,
[http://www.mindvalley.com/goal-setting-
redefined#sthash.aYjq...](http://www.mindvalley.com/goal-setting-
redefined#sthash.aYjqm9Dq.dpbs)

Basically, the mind is what feels "stuck" or anything for that matter, so
anything you can do to calm the mind will help you to see a change. The time-
tested approach is Meditation.

Another one, thinking and doing something for others beyond your immediate
family without any returns - whether it is for those in your community or the
other side of the world.

Hope this helps.

------
kin
Since you said he's always working on some startup to become the next
millionare I'm assuming he is surrounding himself in that culture. Wouldn't he
also be on HN?

Anyway, although it's hard to sympathize for someone that seems financially
stable with a wife AND a newborn to not have a purpose in life, try
surrounding him with friends and activities. What are his hobbies (besides
startup life)? Tell him to watch some TED talks discussing this same thing.
Hell, volunteer! The culture shock of helping those in need should make one
self aware of their luck and privileges vs. immersing yourself around people
who strive for the next big thing.

------
InclinedPlane
Save money like crazy, then retire into a part-time job and do whatever you
want. Pick some hobbies or ambitions and work on those. It's not about making
enough money to demonstrate your status and live a life of ease, it's about
making enough money to be free from having to do work you don't want to. Build
a home shop, lab, recording studio into your house. Buy a yacht to sail around
the world with. Spend your time climbing mountains, hiking trails, or even
just going to the theater or the symphony. Also, think about getting involved
with a non-profit or a charity when transitioning into that part-time pseudo-
retirement.

------
herewego
After figuring out what would fulfill him, he should consider starting his own
venture doing exactly that. A venture is my material representation of
freedom, his may differ -- the take away is that freedom is what enables you
to get unstuck. I used to be in a similar position, making good money as a
tech exec and feeling stuck. The freedom to impact the world, in my chosen
fashion, was the cure and my only regret was that I didn't figure that out
sooner. The most surprising thing to me was that the money side of things
accompanied the impact I was able to achieve, without making it a focus.

~~~
frankphilips
Man, I guess it's not just him....I didn't realize so many fairly "rich"
people struggle with this!

------
jshq111
I hit a similar psychological patch a bit later than your friend (low. 30s). I
would never tell someone to have kids if it's not what they want in life just
as a punt to see if it fills a void. I will say that after having kids I found
a level of meaning in life I never expected (I was never anti-kid but being a
dad wasn't something I dreamt about either and I had the standard
fears/reservations). It's not 100% but I have vastly less angst now that I'm
not fulfilling some grand cosmic mission with my life. I've found happiness a
different way.

------
rbchv
[http://helloimnadia.com/post/68175306402/how-to-ensure-
finan...](http://helloimnadia.com/post/68175306402/how-to-ensure-financial-
independence-in-the-long-run)

The above article seems like a good point of view. Basically achieving the top
1% is an ideal that's sold to us but very very unlikely to become reality. A
much better approach would be to find contentment in what you're doing.

------
codva
He's 25. His life isn't even 1/3rd done. It's pretty rare to even know what
you want to do at that age, let alone have actually accomplished it. What your
friend needs is some perspective on just how great he is doing. However, I
don't have an answer on how he gets it. A lot of it comes maturity I think.

------
plcancel
"Like he hasn't accomplished what he was called to do in life. He's always
working on some startup trying to become the next millionaire but continues to
fail."

Is the calling to be the next millionaire or is being the next millionaire a
substitute for what he thinks might be his calling?

------
erichurkman
Any hobbies or interests beyond work, kids, and cooking? Not saying those are
bad interests, by any means. But there is a lot out there. Specifically, some
interesting hobbies that tend to cost a lot (learning to fly a small plane,
sky diving, traveling, etc).

------
mark_ellul
I would suggest he looks for a Life Coach. They will help him find the source
of his feeling "Stuck" and help him find some objectives that will help him
find meaning and purpose!

------
rajacombinator
What are you trying to fix?

Is he supposed to just accept a mediocre wage-slave existence and settle into
obscurity?

That works for some, but if he wants to strive for more, let him.

------
yachtintransit
Your friend (and wife) needs adventure not success.

------
AnimalMuppet
Maybe the problem is that money can't buy what he's really wanting, but he
doesn't realize that that's the problem.

------
grokas
Ask him what he wanted to do as a kid. Chances are he can afford to experience
a bit of that now, and maybe share that with his family.

------
wanda
some nice walls of text here. If you can't do, teach. Tell him to love his
wife and spend as much time with her as he can, if he values her more than his
own ego. There's plenty of time to get that winning idea. He isn't some freak
from a Stephen King novel and he doesn't need therapy or any tibetan bullshit
for dead people.

------
seiji
Yeah, sure, "friend."

I'm curious where you're from. Who refers to people as "25Y old male?"

------
virtualsue
Why not tell him to keep at it. He's only a failure if he gives up on his
dreams and stops trying.

------
Apreche
Stop reading startup sites every day.

------
xeroxmalf
Sounds like perspective is needed.

------
zoner
Tell him to start paragliding :)

