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25Y Male making over $250K+ annually. Still stuck. Help?

32 pointsby frankphilipsover 11 years ago
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't a showy family. They both drive used cars, cook at home, max out their 401K, etc. However, my friend still feels "stuck". 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. What kind of advice can I give him?

39 comments

daviduover 11 years ago
He doesn&#x27;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.<p>His expectations are either unrealistic, or he&#x27;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.<p>Silicon Valley can be a totally distorted place where there is always someone doing better. It&#x27;s important to look inwards for satisfaction, and not externally, or some arbitrary barometer of success.<p>Plus, the people around him who appear to be winners, are often chock full of their own problems.
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austenallredover 11 years ago
Honestly, have him read &quot;Walden&quot; by Thoreau. Here are a few of my Kindle highlights.<p>&quot;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.&quot;<p>&quot;This spending of the best part of one&#x27;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.&quot;<p>&quot;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.&quot;<p>&quot;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.&quot;
zobaover 11 years ago
I deal with this concern myself, and the answer I&#x27;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)<p>In the Bay Area, things are very expensive and its hard to put money away, and its also hard to feel like &quot;you&#x27;ve won&quot; because other folks are so dramatically more successful than you. However, after visiting home for Christmas I realized that I&#x27;m actually quite successful. So the problem is that I&#x27;m a small or medium fish in a very large pond. So I don&#x27;t ever feel like I&#x27;m free because I&#x27;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).<p>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&#x27;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.<p>Thats where my thoughts are right now, it&#x27;d be great to hear an update on what he thinks about it.<p>EDIT: I wanted to add this follow up. One of the interesting things about this conundrum is, for me, not being as successful&#x2F;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&#x27;m not successful enough, but the worry depresses me enough that I can&#x27;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?
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tomrodover 11 years ago
There are a number of things to consider. Finding accomplishment in life is something many struggle with.<p>Perhaps your friend would feel some accomplishment by:<p>* Mentoring new startups<p>* Mentoring disadvantaged youth<p>* Religion<p>* Community service&#x2F;projects<p>* Becoming involved in local government service<p>* Horticulture<p>* Woodwork&#x2F;old car restoration&#x2F;old computer restoration<p>* Adopt an elderly neighbor as a &quot;grandparent&quot;, that he goes and speaks with on a regular (at least weekly) basis<p>* Read the works of the greats, genre open<p>* Pick up painting or other artistic ventures<p>* Set a goal that&#x27;s a lot of fun. For example, I know of a friend who has a life goal to hike each US state&#x27;s highest peak or point. He&#x27;s made it about 15 in, and has a lot left to go.<p>* Get involved with the local Boy Scouts&#x2F;Girl Scouts program (related to mentoring), if Boy Scouts go through Woodbadge (extensive leadership training)<p>* Join a nonprofit board<p>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&#x27;t always going to be an avocation. When avocation and vocation conflict, I believe a lot of people get dissatisfied.<p>Of course, I could also be completely wrong and a therapist is advisable. But it&#x27;s something to consider.
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Haul4ssover 11 years ago
Quarter-life crisis. He&#x27;s asking &quot;is this all there is?&quot;<p>Not everybody feels compelled to a higher calling. In fact, I&#x27;d say most people don&#x27;t. That doesn&#x27;t mean life isn&#x27;t worth living, it just means he hasn&#x27;t found something that he can pour all of his extra energy in to.<p>Edited to add: Trevor Blackwell used to have something on his web site about founder&#x27;s stories. I can&#x27;t find it now. Basically, he was saying that people want to hear inspiring stories from founders about their &quot;a ha&quot; 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&#x27;t make for a good story.
USNetizenover 11 years ago
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.<p>I wish I had followed that advice at 25.
quaffapintover 11 years ago
Just let him know that I&#x27;m nearly twice his age, make half as much, fail at startup ideas and feel stuck, as well. That should make him happier.
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epipsychidionover 11 years ago
What kind of job pays a 25 year old 160k with flexible hours? Genuinely curious.
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rthomas6over 11 years ago
Maybe this will help:<p><a href="http://www.mrmoneymustache.com/2011/10/02/what-is-stoicism-and-how-can-it-turn-your-life-to-solid-gold/" rel="nofollow">http:&#x2F;&#x2F;www.mrmoneymustache.com&#x2F;2011&#x2F;10&#x2F;02&#x2F;what-is-stoicism-a...</a>
codexover 11 years ago
Does he live in SV? The culture of SV is the rat race with a small but showy percentage breaking free.
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PaulRobinsonover 11 years ago
When you earn a decent wage, most people assume you&#x27;re set for life, however you&#x27;re not. In fact, it can cause problems that most people can&#x27;t perceive.<p>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&#x27;t have quite as much left over as you would expect.<p>You don&#x27;t need to be showy for this to happen. I know people on equivalent salaries who don&#x27;t own cars and live in small flats who don&#x27;t have a lot of spare cash.<p>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&#x27;re not too happy with in order to just stay where you are. Meanwhile, the industry moves on and you feel as though you&#x27;re stuck in the same place and eventually you&#x27;ll get eclipsed, so you throw yourself into staying ahead and all you&#x27;re doing is running on a conveyor belt.<p>There&#x27;s no easy fix. What I suggest for your friend is to focus on that concept of freedom.<p>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?<p>Live on less. Stockpile the cash. Realise you can buy a home outright with a few year&#x27;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&#x27;re spending virtually nothing and you can live on that stockpile for 5 years. Then 10 years. Then 20 years. Then realise you&#x27;re free. Stop working for somebody else. Throw yourself into something you love.<p>I&#x27;ve been in a similar position to your friend - the only way out realistically is to live on less. Chasing more is a fool&#x27;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.<p>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.
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jackgaviganover 11 years ago
Freedom comes from within.<p>Your friend&#x27;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&#x27;s important that he realises that he&#x27;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.<p>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&#x27;t feel free to do now.
minimaxirover 11 years ago
&quot;High paying salary&quot; and &quot;continues to fail&quot; are contradictions and very unusual.
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joshbaptisteover 11 years ago
I don&#x27;t get this rush to have a full blown family in your early&#x2F;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&#x27;t have this void feeling inside and ready for whatever my current long term relationship brings about.
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blahwoopover 11 years ago
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&#x2F;life at age 25 but he has the luxury to balance it with what his household income is at the moment.
nicklerover 11 years ago
He&#x27;s stuck in the success trap. You&#x27;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.<p>I wrote a couple pieces on this at startupathlete.com.<p>Protip: millions of $ =&#x2F;= success. Ask any millionaire what they would wish for and it&#x27;s not another million $.<p>That being said, one of the best questions to ask when someone is in a rut is, &#x27;if money was no object, if you had millions in the bank, what would you be doing&#x27;. The follow up, &#x27;why aren&#x27;t you doing that&#x27;, will always have some excuse about money, which is bullshit. It&#x27;s about fear, security, and risk tolerance.<p>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.<p>Wish you both the best of luck.
garyfirestormover 11 years ago
I think, in his situation, he is doing his best. Not a lot of people earn so much money. Not a lot of people&#x27;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 &#x27;founder - millionaire goal of life&#x27;. People who criticize such goals, I believe do not have big dreams, or for some reason, they can&#x27;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&#x27;t decide his goals, or can&#x27;t call him stupid for chasing million dollars. I guess that answers the question.
joeboover 11 years ago
Just wait until the newborn gets a little older. I have two kids under 3 and found a renewed sense of purpose as they&#x27;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.
michaelrhansenover 11 years ago
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&#x27;t done to be the next big millionaire, but b&#x2F;c they felt compelled to create something awesome.
hariisover 11 years ago
What he needs is the &quot;big picture&quot;.<p>This can be acquired in several ways, depending on the personality of the person, from what I have seen.<p>So a few different things:<p>Recently, I saw a good talk by MindValley CEO, <a href="http://www.mindvalley.com/goal-setting-redefined#sthash.aYjqm9Dq.dpbs" rel="nofollow">http:&#x2F;&#x2F;www.mindvalley.com&#x2F;goal-setting-redefined#sthash.aYjq...</a><p>Basically, the mind is what feels &quot;stuck&quot; 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.<p>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.<p>Hope this helps.
kinover 11 years ago
Since you said he&#x27;s always working on some startup to become the next millionare I&#x27;m assuming he is surrounding himself in that culture. Wouldn&#x27;t he also be on HN?<p>Anyway, although it&#x27;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.
InclinedPlaneover 11 years ago
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&#x27;s not about making enough money to demonstrate your status and live a life of ease, it&#x27;s about making enough money to be free from having to do work you don&#x27;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.
herewegoover 11 years ago
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&#x27;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.
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jshq111over 11 years ago
I hit a similar psychological patch a bit later than your friend (low. 30s). I would never tell someone to have kids if it&#x27;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&#x27;t something I dreamt about either and I had the standard fears&#x2F;reservations). It&#x27;s not 100% but I have vastly less angst now that I&#x27;m not fulfilling some grand cosmic mission with my life. I&#x27;ve found happiness a different way.
rbchvover 11 years ago
<a href="http://helloimnadia.com/post/68175306402/how-to-ensure-financial-independence-in-the-long-run" rel="nofollow">http:&#x2F;&#x2F;helloimnadia.com&#x2F;post&#x2F;68175306402&#x2F;how-to-ensure-finan...</a><p>The above article seems like a good point of view. Basically achieving the top 1% is an ideal that&#x27;s sold to us but very very unlikely to become reality. A much better approach would be to find contentment in what you&#x27;re doing.
codvaover 11 years ago
He&#x27;s 25. His life isn&#x27;t even 1&#x2F;3rd done. It&#x27;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&#x27;t have an answer on how he gets it. A lot of it comes maturity I think.
plcancelover 11 years ago
&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.&quot;<p>Is the calling to be the next millionaire or is being the next millionaire a substitute for what he thinks might be his calling?
erichurkmanover 11 years ago
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_ellulover 11 years ago
I would suggest he looks for a Life Coach. They will help him find the source of his feeling &quot;Stuck&quot; and help him find some objectives that will help him find meaning and purpose!
rajacombinatorover 11 years ago
What are you trying to fix?<p>Is he supposed to just accept a mediocre wage-slave existence and settle into obscurity?<p>That works for some, but if he wants to strive for more, let him.
yachtintransitover 11 years ago
Your friend (and wife) needs adventure not success.
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AnimalMuppetover 11 years ago
Maybe the problem is that money can&#x27;t buy what he&#x27;s really wanting, but he doesn&#x27;t realize that that&#x27;s the problem.
grokasover 11 years ago
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.
wandaover 11 years ago
some nice walls of text here. If you can&#x27;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&#x27;s plenty of time to get that winning idea. He isn&#x27;t some freak from a Stephen King novel and he doesn&#x27;t need therapy or any tibetan bullshit for dead people.
seijiover 11 years ago
Yeah, sure, &quot;friend.&quot;<p>I&#x27;m curious where you&#x27;re from. Who refers to people as &quot;25Y old male?&quot;
virtualsueover 11 years ago
Why not tell him to keep at it. He&#x27;s only a failure if he gives up on his dreams and stops trying.
Aprecheover 11 years ago
Stop reading startup sites every day.
xeroxmalfover 11 years ago
Sounds like perspective is needed.
zonerover 11 years ago
Tell him to start paragliding :)