I'm 25 years old and I am lost

309 points by mlost ↗ HN
I co-founded a startup couple of years back which got acquired recently. Even though it was termed an acquisition, it was really an acqui-hire. When people congratulate me on that, I know in my heart that it's not true and it doesn't really make me happy.

Now, I've quit my job at that company because I just couldn't work there any longer. And am trying to figure out what to do next.

I know for a fact that I want to run my own business and attain financial freedom but I can't risk another startup at this moment because: 1. Startups are tough and I am afraid 2. I have a few financial responsibilities towards my family which I have to take care of.

Thus, I have picked up another job which I'll join in a few weeks. It is not in a very 'sexy' or 'trendy' industry and I have no idea where it is going to take me in two years.

What do you do when you believe that you can do great things but something that you have no control over is holding you back? You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities. How do you cope with that? Seeing your future as an underachiever pains you. What do you do?

In the course of trying to figure it out, I spoke to my friends about this, I realised that most of them are going through the same thing. But they haven't figured out how to deal with it. I don't know if this is what they call a quarter-life crisis.

Thus, this is as much a distress call as it is a rant. And not having anyone else to turn to, I am posting it here at HN assuming that this is not just a problem for a handful of people but a general problem for people who believe in their ability to do great things (whether it is true or not is irrelevant to them).

The questions I posed here aren't the only ones I have in my mind. But, I hope I have been able to convey the message. Any help would be much appreciated. Thanks!

273 comments

[ 5.3 ms ] story [ 263 ms ] thread
My mom always told me do what you love and the money will follow. Sounds trite but I've spent the last six years going 50/50 between working as a professional skydiver and traveling internationally. Now I am successfully transitioning to web design so I can travel full time.

If it isn't fulfilling then don't do it.

I completely agree with this; however, there is another way to approach the situation. I recently went through almost the exact same experience OP did and decided to cut everything extraneous out of my life and take a remote dev job. This has allowed me to slow life down, re-focus on the things that matter in life and build up my bank account. THIS gives me the freedom to go and create and build and run whatever I want if I so choose.

So, don't feel bad doing a job. Nothing is beneath you, and everything is always a stepping stone between where you are now and where you will be later.

Startups will always be tough and you'll probably always be afraid.

Take care of your financial situation and push on with your new startup.

It is easy to feel panicked when facing a situation you want to change, but I'm sure if you reflect upon your life you've felt that way before and made it through. Problems ahead can often seem insurmountable but few things in life actually are.

There's two ways to look at this that I'll suggest, since I have a certain amount of familiarity with this.

1) You're 25 years old, and already have one acqui-hire under your belt. That's pretty impressive. Considering probably 90%? 99%? of people will never have a startup they build acquired under any circumstances, it seems weird to describe yourself as an underachiever.

There's this weird cult of young entrepreneurship, where it's implied that if you're in your 20s, you must be founding companies or you're just wasting your time.

I'll throw something out there instead - why not spend the next few years working at your day job and trying to learn how to be a better startup founder the next time you do it? Think of it like being in training for the next gig.

2) my other perspective on this:

> What do you do when you believe that you can do great things but something that you have no control over is holding you back? You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities.

That's called "adulthood". Sometimes you have responsibilities that limit your options or make it hard to do what you love.

"why not spend the next few years working at your day job and ..."

I realised recently that my life would be a lot better right now if I worked the so-called soul destroying corporate job because I'd have more money, work fewer hours, have less stress during work, people would expect less from me, I'd have infinitely more holidays, more work-free weekends...

Sometimes its hard to see what you've got until its gone :)

Don't get me wrong, I like being a founder and don't regret it for a minute, but when times get tough I look back and think the soul destroying corporate days were actually pretty good.

Which brings me to this: Life (usually) really is what you make of it.

Yeah, so - I/we started GridApp when I was 23. I didn't have any grand dreams about being a 20-something entrepreneur, I just came to the (accurate, as it turns out) conclusion that it was never going to be easier to completely upend my personal and professional life than it was when I was 23 - no mortgage, no SO, no debt other than student loans, no kids, etc.

When we got acquired, I assumed that I would leave as soon as I could and do it all again - but yet, I'm still here. It's interesting work, and while I miss the ability to just get things done, I find that I've been getting a lot better at dealing with problems at scale. So, for example, how DO you launch a new product to a sales and support organization with hundreds of people?

I'm not saying I'll never start a company again, because I really want to, but I'm enjoying feeling like I'm learning how to do things better next time.

I do like your titles; CEO, CTO, Chief Scientist, Director of Development, and Mr. Database.
A lot of that was an artifact of how we got started - it wasn't quite clear who would be doing what, and so other than CEO, everyone's responsibilities were pretty amorphous.

I got saddled with "chief scientist", but practically speaking it was "technical field operations and product management", which just ends up being a lot to put on a business card.

AFAIK "chief scientist" title assumes that you, or your team of scientists are doing academic research. And that you publish results of your research.

Taking a title like that, while actually not doing it is a borderline fraud. If I'll get a resume with "scientist" or "researcher" in the title, the first thing I would look at would be published academic papers. If there are none, I will not consider this resume.

Well, the origins were far more benign than "borderline fraud" - my original role was doing product research in distributed database design and performance. I gave a lot of talks and wrote a couple of (non-acaddemic) papers on how to build widely distributed database systems, focusing on Oracle RAC.

My job evolved to be more of a business-focused role, but my title did not. The intention was never to mislead, and indeed, when asked, I never claimed to be an academic.

> Taking a title like that, while actually not doing it is a borderline fraud

That seems like a strong conclusion to draw. My title now is "Product Architect", but I'm not an architect, nor do I exclusively design products.

A quick skim through Crunchbase yields:

http://www.crunchbase.com/person/jeff-hammerbacher (bright guy, not an academic)

http://www.crunchbase.com/person/bram-cohen (not an academic)

http://www.crunchbase.com/person/chris-slowe (not really an academic)

And that's in the first 10 results. "Fraud" seems strong.

On the flip side, founding a company can actually give you more time back, depending on the company. I started a consulting biz last year, and have a ton more vacation, slack days by choice, evenings and weekends than I did when working my previous full time job.
How do you started it? How long it took for you to find first clients?
I was vital enough to my full time employer that I knew they'd give me some contracting to hold them over. And, I had a couple of contacts who I knew were interested in my doing some work for them.

I started planning 3 months before I gave notice. Made sure I had 6 months' savings. Formed an LLC, talked with a business attorney and CPA, and lined up projects before my quit-date. So I was basically ready to go from day 1.

So true. I have been working in a corporate job (finance!!) for 9 years. I often dream of saving my soul and working on/founding a startup. The appeal of building something, working for myself, etc is great. But, so is the regular paycheck and benefits.

On which side is the grass greener?

(comment deleted)
"Think of it like being in training for the next gig."

Amazing way to put it. I'm 25 myself and this is the only reason why I'm still working for my big corp. Payed school.

The other thing is, "working for my big corp" should teach you a lot of things, including useful stuff for a startup. With much less responsibility (e.g. you're not worried about making payroll), you have the luxury of observing and thinking about it.
This is my plan as well (also 25). I want to learn from some of the best so that when I'm a bit older I have enough world experience to build something myself. Sure I could build all sorts of apps now, but that is only fraction of the work that goes into building a sustainable business.

I used to think life was a race, but I'm really enjoying the growth and learning parts.

Learning the ins and outs of some particular industry is a great way to get ideas for the next startup. Every industry has pain points, where is the pain in your new company?

Also, 'great things' can mean different things to different people. Like building a marriage and raising children. Everyone does it, so it can't really be that big of deal. Can it? Try and see...

The next job can absolutely be used as training for your next gig. Also, the next job can be your financial foundation as you start your next gig on the side. Running a startup should not put your family's livelihood at risk. My father is an entrepreneur and frequently had several small side projects going on at any given time while I was growing up. Right now, he's focused on building up one business, but another business he built up previously is still bringing in solid income. Several great companies started as side projects while the founders were occupied with some other "real" job: GitHub, Google (perhaps debatable, but it started while the founders were full-time students), Facebook, Basecamp, and the list goes on and on. I once read James Altucher explain that he stayed at his "real" job for two years while he built up his side business. By the time he quit to work on his startup full-time, the startup was already extremely healthy with several full-time employees and enough customers to profitably pay everyone a great salary. Of course, you'll have to talk to your new employer to work out the legality of creating side projects. But if you pursue building something up on the side, you'll be joining a long tradition of entrepreneurs who have done the same, some of whom have built companies that will be remembered for centuries.
This is good advice OP. I'm 28, have co-founded three startups, first one was "acquired" for the technology for an "undisclosed sum" (we all know what that means). I used to feel a little weird about it too, particularly because it chased the splitting of my cofounder and I; ya know what though, I built that technology and it was valuable enough to one of our customers to buy it.

That is definitely more than most founders can say. Don't let startup hype get to you.

The parent commenter said something else I want to echo: take some time and learn from other leaders right now, make money, get a good emergency fund AND a "startup fund" built. Get your hands dirty in other businesses and see what they're using spreadsheets for and what they are doing repetitively -- that's where you'll (most likely) find your next product opportunity.

I don't :) What does "undisclosed sum" mean? Does it mean you got a year's salary, 10 years', or a nominal sum like $1 for the tech and a job?
I legally cannot talk about the details of the acquisition, but it usually means "not glamorous" :)

There's much more to the story, I had blogged about it but svbtle deactivated my account for no reason and is unreachable. If you're really curious about the story I'd be happy to converse privately over email.

> it seems weird to describe yourself as an underachiever.

It is really not that weird.

http://en.wikipedia.org/wiki/Impostor_syndrome

What I hate, however, is knowing about imposter syndrome and letting that screw with my mind. I think, "maybe I am using imposter syndrome as a way to sneakily support my ego that is only partially supported by reality. Reality does not support my ego at the inflated levels I want to believe in." But then I think - well, I suppose I have to be smart to trick myself in such a ridiculous way, and conclude I actually am smart. That leads me to think that I am actually an intellectual imposter, and it's traditional that I take that as a truth, which my ego has temporarily decided to not believe in, for certain problem kinds.

Lately, I build on top of externally developing habits - like studying, running, meditating, eating healthy, sleeping healthy, working at a normal pace, and having confidence in my own opinions about computer science, logic, mathematics, and programming. This helps me think less about how I perceive myself and how others perceive me, but I can get knocked off my horse once in a while. I just try to remind myself that it's just time wasted that I could use studying, working, or helping other people - which is more thinking about the long long term, rather than each individual achievement.

You just described my life so well. Thank you.
You have more freedom than you think to do great and interesting work in the job you have now. Just don't wait to be asked, you just invent without being asked to invent.

You just need initiate and bootstrap the idea yourself on the side quietly, then when ready for demo, show it to your boss and ask for some sponsorship to keep working on it (you gotta make sure it has clear business impact for them) Most reasonable bosses will allow for some time invested in new and interesting ideas. If your boss always shoots it down then find a new boss.

>meant for great things

This part of your post sticks out like a sore thumb. What "things?" How will you know when the "things" you have "done" are "great" enough? What makes you think you are "meant" for them? What does "meant" mean? Was your birth heralded by a double rainbow or something?

I'm betting that "great" is defined relative to some imagined ideal that you can never reach, or which you will constantly shift to ensure your own continuing dissatisfaction.

Decide what you want.

Yeah, that stuck out to me as well. Thinking like that is a sign that there may be larger issues at play here. Truly satisfied and happy people don't believe themselves to have been destined for greatness in any such manner - even though they may or may not be as "great" as anyone else. And conversely, truly "great" people, are often the benefactors of circumstance and luck more than anything else. Focusing on attaining the greatness that you were destined to achieve is a recipe for lifelong disappointment.
Not attempting greatness, because of risk of disappointment?...I feel something is missing there. I don't have any answers yet though. There must be a third way.
There's an important distinction between simply being ambitious about achieving greatness, and feeling as though you were destined, or meant, to achieve greatness. The former accounts for failure, while the latter does not.
This makes sense to me. In a lot of way, the current generation seems to have a lot of folks suffering from 'special snowflake' syndrome. It is drilled into people at school, 'you are special! You are destined for greatness!" But the reality is that they don't tell you theat most of the great things in life are free...

A good family and children, personal happiness, friendships, love. These things make a person happy and satisfied. Even relationships I've had when waiting tables and the pride I took in doing that work was extremely satisfying (even if the hours were bad and the pay mediocre). But that was because of my attitude and goals, not because of the work.

Now, I work at a very very large software company doing interesting, challenging work and am paid well for it. Despite all my great coworkers and satisfaction in doing my job, they are not going to keep me company or be my real friends at the end of the day.

Work to live, my friend, don't live to work.

> I have no idea where it is going to take me in two years

No one knows the future. The best experiences of my life have been things I hadn't even thought about a year before they happened.

> You believe that you are good at what you do and are meant for great things but you have to do your job even though it doesn't do justice to your capabilities

Spend one hour per day working on your own project idea. Maybe it will turn into something, maybe not. But at least it will be something you own and you'll learn a lot from it. Does it suck that progress will be slow? Yes. But 1 hour per day over the course of two years can add up to something pretty impressive.

I have 2 kids under 2 and I am working on 2 startups at once. That is basically like having 4 babies. I don't believe you should necessarily wait for the right time, for any kind of baby. There may never be an ideal time. If you have something you are passionate about you go for it. If you don't then you bide your time.

I have gone through periods of burn out and extreme passion about my startups. Sometimes it's nice to have a steady paying job and be stress free for a while. That's you biding your time until the right idea/opportunity comes along.

I went through an acquihire myself. Don't feel bad, startups are a longshot, and to see any positive outcome is much better than nothing. I worked for that company for 2 years, became frustrated, had an idea I was excited about, and then started something new.

So my advice is, take the stress-free job until you build up the passion to work on something new. And then do it.

EDIT: typo

Are those two actual startups, or more like two mirco "startups"? In other words, are you trying to get both of these startups to grow massively fast, or are these just businesses to cover your living expenses?
This is not a definition of "actual" startups, just of those who have an imperative to grow "massively fast", usually because they have taken external, primarily VC, funding.

A startup is a new business that is still investigating what kind of product it is going to sell, and to which audience.

Genuinely curious, why do you think this is an important distinction?
Sorry for the delay in response... I would call them actual startups.

For one I raised $1.7m in money over the years several years ago, but then had to scale it back due to lack of success. I pivoted it to a site that now has millions of visitors per month, but I run it solo trying to figure out how to make money and grow it.

The other company is just two us, my cofounder and I created a social media analytics platform and we have done about $150k of revenue in bootstrap mode in the past year or so. We are now trying to push a product to the masses and may look for funding soon.

Don't beat yourself up too much. Doing great stuff takes time, you learned a sh*t load from your last company and next time you can avoid some of the mistakes. As irritating as it is to endure - doing a mediocre job should give you some respite, time to think and the ability save some cash.

Aim to save the maximum humanly possible (reduce spend/be frugal) to give you potential budget or run-way for your next project. Start it while you are employed, work on it when you are at work. Be a terrible employee while more-or-less still looking good... but vest your time in new projects or ideas, or exposing yourself to where you might find them (not pointless crap like most other bad employees do).

Personally, I am in the latter stages of 'medicore job' period after a very similar gig at a fairly similar age (few yrs older). I am hitting 70% net wage savings rate and have one project in-hand progressing reasonably well and a bigger/ambitious project in the works. I spend the majority of my work day working on these projects while still delivering for my job - I really dislike working for someone else but, as a means to an end, this is pretty cushy.

Hunker down in the new job for a couple of years, don't fall for needless lifestyle upgrades just because you have a salary now (Mr Money Moustache methodology) and come back to a start up in a couple of years if you want to with a bit of cash under your belt and a new perspective.

Good luck what ever you choose, it's likely that there are no bad choices right now which is why you're feeling like this.

I'd say there's 3 things to consider

* You should be really proud of your achievements so far, an acqui-hire is no joke.

* I understand you may be afraid of starting or joining a risky startup. But what have you got to lose? At age 25, you can live a scrappy life, there's no social pressure not be a salary man anymore these days, especially in a startup scene where it's so normal. You're young and can take the risk.

* Third, the only point that really matters in my opinion, is the people you have to provide for. If there's no way around it, there's no way around it. I know what that's like and I respect that. Just make sure to check your assumtions carefully. I'd had to take care of my sick dad for a long time, but wouldn't throw away an opportunity I really believed in, as he'd hate himself if he was an obstacle, and he'd still have my mom and my bro, and I'd still be able to support him partially. Talk to those who you support, and consider if they really depend on you. Sometimes there's room to juggle both, sometimes it's possible to find an alternative caretaker.

Lastly, there's quite a few startups that are challenging and do pay decently from the get go. Bitcoin is a fun space for example, and Bitpay and Coinbase pay well, yet exist in a challenging and ever in-flux ecosystem.

(comment deleted)
Sounds like you are a perfectionist in nature :) Perfectionist tend to be rarely "happy" with their achievements and are always striving for more. It is very hard to be fulfilled with such a mindset. I would suggest checking out this book with some more information on being a perfectionist http://www.amazon.com/gp/product/B004BKJB6Y/ref=oh_aui_d_det...
You're so young, enjoy the ride.

Cultivate a rich life and identity outside of work. It's hard but what we do doesn't have to be what defines us.

When I was 21 I started a company with 4 other people that lasted about 2 years before we ran out of money. After that I went to work for an insurance company. At the age of 26, the contacts I made from my startup started to blossom, and I got back into a trendy company that I stayed at for 6 years before breaking off on my own again around the age of 32.

Here's the thing, I was worried about going backwards in my carrier when I went to work for the insurance company, but instead it taught me discipline and gave me the chance to learn from veteran programmers. I would not trade in those years for a new startup firm.

Don't feel like you're giving up just because you have to step back a bit. Use it as a chance to get a different perspective on our industry.

Holy crap man, this is almost the exact same boat I'm in (except I'm 26) and I feel the exact same way.

I find my biggest problem is a lack energy / motivation to start that next thing. I really have no clue where the fuck it came from... a few years ago I could work endlessly...

You're burned out. Be very afraid of this.

If you can afford to, take a long vacation. If you can't, try to find something that brings you joy and do that thing every single day, without fail. Beware of burnout, it can cost you years.

Stop the presses. Go travel for a bit. See the world.
Why do you want to run your own business? What are the positives you hope to gain from doing that? I spent my mid-twenties convinced that I wanted to found a startup and live that life, but having recently emerged in my 30s I've realised that what I actually wanted was the freedom to make my own choices about what I work on and how. I never cared about entrepreneurship.

I left the startup world behind and my life satisfaction went through the roof - I no longer felt guilty for not crushing it 100%, or that I hadn't sold a successful company by the age of 24. I'm not saying this is the answer for you, but it's never a bad thing to get some perspective. Get out of the bubble - take a road trip around some states, maybe. Take a break from Hacker News. You and your friends might be chasing the wrong thing.

> I've realised that what I actually wanted was the freedom to make my own choices about what I work on and how.

What are ways to accomplish this without running your own business?

Not OP, but not every business is a startup. Freelancing or building a consultancy might give you freedom without a 90% failure rate.
Welcome to the human condition.

I received some advice a number of years ago which has stuck with me, and served me well.

If there's something you want to do with your life... Don't talk about it. Don't think about it. You'll do so forever.

Just do it. You'll be 50 before you know what the hell happened.

Exactly this.

Another advice from a book, which stuck with me: "If you have the desire to do something, do it, because if you wait too long, you will find that the desire has left you long ago."

I have done everything I wanted to do in my 20s. I have a technical/developer background but left my startup career, with no job offer or backup nets, became a SAG actor, and a whole lot more. I even wrote and published a bunch of eBooks on this too.

BEST MOVE EVER.

I now have professional resumes in 3 different industries. Acting, Sales, and Startups. Great diversification. I even joined another startup years later doing something much more fun. The career gap came up, but I just told it like it is. You will find open-minded people who want to work with you.

Now I'm in my early 30s, happily getting ready to settle down. Just follow your heart. It's healthy and normal to yearn for great things. That is because YOU are pure greatness. Those who take action will distinguish themselves from those who don't.

What do I want to do in my thirties? Be a life coach to share my experience to those who find value. Be a great father/life partner. Learn to surf.

Make 'peace' with your 'current' situation.

This does not mean 'accepting' it and 'acknowledging' that mediocrity is all you're bound to. This means that for the time being, you will make the 'best' of the opportunity 'at hand', you will work for a better one to present itself while eliminating all the negativity and irritation associated with the present.

Changing your mental state, to become a catalyst for progress instead of a shackle, is the actual problem and the real challenge. Work on this point, the rest is relatively clearer (side projects, another startup, better offer, fancier pay, more exciting challenges/problems to solve etc...).

I'm in the same position, at the same age, battling the same demons. The above is my realization after a prolonged phase of depression. 'Work with what you have to reach what you couldn't before'.

You might have Imposter Syndrome. Take a step back, and make a list of all your accomplishments. This is not about being self-centered, it's about taking a honest view of your life. During the day-to-day shuffle, with short-term deadlines and other obligations, it's easy to forget about the long path you've taken to get to where you are.

You co-founded a company that was acquired - how many people can say that? Even if it was an acqui-hire, does that really make a difference? Why do you feel that this accomplishment is not worthy of praise?

You didn't like working at the parent company and so you left to find different work. What is wrong with that? I would bet that most people on HN have been through a similar circumstance. If you don't like working at a certain place and don't fit it, it's not necessarily your fault or anyone's "fault".

Furthermore, you had the ability and confidence to leave a job you did not like and take a job that perhaps will be a better fit. Why does it matter that it's not in a "sexy" or "trendy" industry? Reading just the big headline stories on HN or other tech websites will leave you a bubble where it seems like everyone is working for an ultra-trendy hipster startup that will be "the next big thing", when in reality many software developers work in more mundane industries but are still very technically astute and have a fulfilling life.

If it's something you can do day after day and it doesn't bother you, in my mind that is great. Don't compare yourself to what others want, compare yourself to what you want.

Which leads me to my next point: Why do you believe that you are an underachiever? Compared to what benchmark? There is nothing wrong with being ambitious - motivation often provides the drive to succeed. But if you are always left wanting more, then you never really get to savour the reward from your efforts and hard work.

Take a step back and try to figure out what really fulfills you in life. Work is often treated as a means to an end, and there's nothing wrong that. However, some people really do relish work and for them, that is an end in an unto itself. But if that's not what fulfills you, you shouldn't try to pigeon-hole yourself into someone else's goals by way of comparison.

A guy with an acqui-hire under his belt describes himself as an underachiever -- I don't think you realise how insulting that might be to other ambitious people who are in much, much humbler places :)

Grab that bag of money and go travel if you can. Have a good time, you deserve it.

I think reframing the way you're thinking about this would help.

Instead of saying "I'm annoyed that I can't do these things arg" why not say "I've made a decision to do Y because, and I'm going to make the most of that." Next, try to evaluate whether you are succeeding in that role. Are you learning? Growing? Maybe you're not coding as much but you're learning a crap-ton about how NOT to do things, or about a business domain that has a bunch of meaty problems you can solve later.

Look hard at the things you really want that make you happy (spending time with family, creating things, etc) weigh them, and use that as a new target.

Unfortunately your conundrum is a constant struggle throughout life for those that want to have an impact. First, breathe and relax, and know that it is impossible to do everything all the time. Second, realize that you have a bunch of time left, and there is no formula that determines when in life you can have an impact or be successful. You'll be just fine.

Just because your current job isn't in a sexy or trendy industry doesn't make it bad. You can learn a lot about working with people and business even if you're somewhere in the bowels of a large multinational corporation. I know I have. Also, there are really excellent developers in companies like that, too, not just in startups in the valley. Even if this job isn't for you, a couple years in a place like that isn't very long in big scheme of things. You might get ideas for some sort of B2B startup that you wouldn't have otherwise.