Climbing the wrong hill

You've captured the Dip described well by Seth Godin. I have long thought about this local optimal trap we fall into in our lives.

Last year I was fortunate enough to make a drastic change and reset my work life after almost 6 months of seeking out a passionate and meaningful calling. I love to write and share, an have been fascinated by the creation and uncovering of latent value achieved by entrepreneurs.

While I work part time at my old position (they want my effort full time for the next few weeks and I'm torn between getting paid now or pushing a project further faster). I really could use the extra capital short term to help wedding costs next year and the nascent startup. As long as I am strict with the duration of my full time return I see it as a viable option.

Poignant post to where I'm at now. Best of luck to us all in finding a path that is powered forward by our inspiration, interest and passion.

Seventh popular post down, 8/10

Hi Chris,

As always, an elegant idea. I had a thought motivated by this idea of "climbing up the wrong hill," as I've been involved in some startups (and a big one right now), one of my advisers said something that struck me: He said, "Hey, make sure you're seen as the glue, not a lego." He was implying that b/c I'm around a lot of scientists, and technologists, etc. that people with more general skills and backgrounds need to make sure they are seen as vital to the connective tissue of the enterprise--and not as an interchangeable part.

premature optimization is the root of all evil (c)

Quoting Warren Buffet...climbing the wrong hill is "like saving sex for your old age. It makes no sense."

Hi Chris,
I really like this blog entry and your observation of people's tendancies to settle at the local maxima rather than heading towards the global maxima. Fantastic analogy. I've been thinking a lot about it and just wanted to note that it applies across different parts of life -- for example, relationships. A lot of people stay in mediocre relationships longer than they should.

Let's say the person you're dating isn't your soulmate - you're not going to spend forever together and get married. So why stay together? It's the local maxima thing again -- it beats being single! But like staying at a bad fitting job, it harms you because you're wasting your time climbing the wrong hill.

Jonathan

P.S. Have you read Steve Pavlina's "why you should never get a job?" http://www.stevepavlina.com/blog/2006/07/10-rea... -- makes some really good points about how trading your time for money doesn't scale and will rarely make you rich. You need to take risks and get ownership.

great comment and thanks for the link - really enjoyed it, especially "Income for Dummies"

I stopped reading after you talked about the algorithm of the hill. Huh? What?

Makes sense after you've reached some sort of peak. Until then, during the time when your post-college friends are busy traveling, shopping and having fun while you feel like a mud ridden warrior who does nothing but trek through this forest....all while all of your family and post college friends who are working for big name impressive companies think you have just lost it... a little glimpse of a peak doesn't hurt. This article doesn't either.

In reality there is probably never a case with 100% visibility - e.g. your friend has no way of knowing if he'd joining next Google or next Webvan. He'd probably enjoy the ride regardless but if we optimize for "height" we'd still be playing probabilities so it is at least to an extent "foggy".

Secondly, implicit in this decision making is that grabbing the short term carrot of getting higher now increases the stick - the "hill-switching costs" longer term. So what is one already on a wrong hill to do? Interestingly, an INSEAD professor published a paper a while back "how to stay stuck in the wrong career" http://www.insead.edu/alumni/newsletter/january... exploring this very issue. To steal her thunder and to save you reading time - not surprisingly she found the probability of hill jumping decreases the further up the wrong hill people get. For those who do jump abruptly the chances of recovery, assuming a multi-hill environment, are rather slim. It is the ones who undertake experiments, to continue the analogy - parachuting on various hills for a week-end hike - who are most successful in hill-switching.

As someone who climbed one of those lower hills a while back, I thought this was a great post. I studied computer science and it's only now, after years on Wall St., that I'm in touch with what I really want to build and want my work/life to be like.

I still recruit from universities and I'll be sure to point to your post when I ask students "What do you want to do?" so we can have a genuine, thoughtful discussion about it.

This was a great post. We often shortchange ourselves by not being patient enough for future rewards and grabbing at the opportunity in front of us. I think at a certain point, time is the one thing that we can't purchase and time wasted on efforts that aren't central to where we want to be in the future is a huge waste and the one thing we can never retrieve or replace.

This was a great post, thanks.

nicely written...

Bookmarking... very insightful articles and first hand comments are all two thumbs up. At the end I agree with David that what matter most is your happiness. Youngster should always risk, you guys got less to loss. In the end it just a matter of discipline and consistency.

Chris, you reiterate the notion that startups thrive on talented CS/engineer whizzes. Assuming they're not programmers, what value do you see in the recent college grad/i-banker/consultant? How and where do you see their skills leveraged to accelerate growth? I think this particular demo is harvesting a pool of talent - it's just a question of figuring out the best way to tap into it.

i really like the notion of adding a bit of randomness. Wish someone could have told me this senior year of college

vey good.. thought.. and nice example to convey it..

This is a very valuable post. I hope this post reaches some of the young and ambitious professionals who are really into "career management". For example, over the years, I have run into many individuals who told me things like "I started my career at McKinsey. After business school I added another name brand such as Microsoft/Google/whatever. Joining a no-name start-up will dilute my brand. blah blah".

Your made a great point of adding randomness to one's career. I think in today's world, career paths are becoming less and less linear. Focus on what you like to do, give 100% in your current job, and it'll take care of the rest. No need to worry too much about your next career move. It'll come if you're enjoying your current job and doing a great job.

Thanks for posting that. It is encouraging, especially since I've continuously searched for that "10-year" goal, which has led to a bit of career meandering but ended up landing me where I'd wanted to go nearly 7 years prior when I left b-school: a startup. Of course, I think it is far easier to make the shift early in one's career (i.e., immediately out of school or a couple of years afterward) than it is to make a move in that middling age (early to mid-30s) when one's career trajectory is being cemented and the social pressures of one's peers are among their strongest.

Great post! I did management consultancy for 10 years, in 5 languages and 7 countries, but I knew this wasn't my future. Probably I should have stopped climbing the wrong hill some years years before taking the decision to look at the right hill. Better late then never ;-)

Topic for another post: How does the highest hill problem interact with the need to truly understand customer pain points to create value in a startup? If every potential entrepreneur goes straight into startups, how do they figure out what problems other people have? Or do all their new business ideas revolve around solving problems for people like themselves?

I'm not sure what the right equilibrium is, but I think there can be huge value in working in some other field to really figure out how screwed up it is, how you could fix their problems, and how you could sell that solution to them.

To put a really controversial spin on it, I would argue that the straight-to-startups phenomenon is one reason why there are too many me-too startups out there (note: assumed for the sake of argument). People often haven't collected enough grist for the mill to come up with an idea that's really out of left field in the startup world but brilliant for some vertical or horizontal market that just doesn't intersect with high-tech that much.

Ok so what kind of methods would you suggest to find ways of getting beyond the me too! (let be known that I think that sometimes the better startups are the me too, they are just iterating around the idea until they hit upon the best mix of what makes the idea good in and of itself)

Scary appropriate.

Like the new theme, much more reader friendly!

I agree, I think the centering and san-serif treats you right! (though I'm am a serif person myself)

Good advice overall. Much like the computer science problem it is drawn from, there are 2 difficulties: How do u choose randomly where to start? How do you know when it the highest hill?

Our starting point is often tied to our past experiences and to a lesser extent the people we know, so it will not be truly random.

The more important point, how can you tell when you are on the highest hill? Maybe you can see higher ones but you will never know when you are on the highest. Its like saying you want to optimize happiness.

Kind of off-topic but the 'Subscribe...' bookmarklet for Google Reader doesn't work for your page. I had to paste the link in Reader to subscribe to your blog.

huh, i've been trying to fix this but can't seem to. i'm using off the shelf wordpress so you'd think it would work. any suggestions would be very much appreciated.

It was easy to read this post, as someone in a startup, and to assume that the "higher hill" is the startup. Of course, I think you have made clear in comments (and it is clear if you think about it) that which hill is higher depends on the person - beauty is in the eye of the beholder right? :) And the Z axis therefore is not necessarily $, but you could say, self-actualization or some such.

I think the real trick is understanding what you care about - not just which career - but why each career helps or doesn't help you achieve your own personal goals. Understanding how you compare the height of each hill is pretty important - otherwise you may pick based on some external, measurable metric ($$) and not on something that may turn out to be more important (making a difference in the world? mentoring others? family life? lifestyle? etc.)

Good food for thought.

Good comment. The z axis is happiness.

I probably should have made it clearer that I meant the Z axis to be personal utility or something like that. I personally have a clear bias toward startups but that is beside the point I was making in this post.

Look up your ladder. Do you want anyone's job up there? If not, move on.

Interesting post, Chris - indeed, I saw the same issue working at two major law firms in New York City: bright, talented and ambitious young lawyers who hated their jobs, but didn’t have the kahunas to quit to pursue their dreams. Why? For a number reasons – “golden handcuffs,” inertia, fear of the unknown – but I think the number one reason is societal pressure – i.e., pressure (whether express or implied) from parents, teachers and peers to stay on the “accepted” path -- the path to “status” and “prestige” – the well-trodden path.

Fortunately, I found the strength to walk away from the big-firm partnership and move to California to launch my own law firm - but it wasn’t easy on a personal level (and I had to cut-off a lot of naysayers). My advice to all the young, bright and ambitious students is to read Nietzsche (one of the most misunderstood philosophers who ever lived). As he wrote in The Gay Science: “[B]elieve me: the secret for harvesting from existence the greatest fruitfulness and the greatest enjoyment is—to live dangerously. Build your cities on the slopes of Vesuvius! Send your ships into unchartered seas! Live at war with your peers and yourselves!”

Cheers.

chris - great post and great advice. but mostly i stopped by to say i am really digging your avatar. it's excellent!

thanks! my coworkers say it looks like a cooler version of me, which I guess is the goal of an avatar :)

that's why i use the one i use

Yup.

Would be interesting to poll successful entrepreneurs that spent 5+ years in "industry" before going the start-up route. When did you go start-up? When would it have been optimal? I worked at Accenture for 5 years before getting into the software sector and it was 13 years before I started my own company. I don't regret any of the experiences, but could have done better for myself if I cut both numbers at least in 1/2. I bet others would feel the same way.

I spent 4 years working at a startup instead of starting one. Honestly, I wish I had just started starting things right out of college.

Very interesting thoughts and a great post. I often advise younger people that their first years out of college are the time where they invest in themselves and that that initial investment of time will yield dividends when they are in their late 20s or early 30s. Smart plus experience and wisdom is almost always better than just smart alone. Then the question comes back "where should I invest my time?" and I give a similar answer - preparing to do something you will love to do for forever. I was lucky enough to have the example of my father who has loved his job every day of his life and therefore have seen what a difference it makes. Life is way too short to not enjoy what you do for a living since it's what you will spend a vast percentage of your life on.

If you want to be a wall street quant above all else - definitely go to wall street and get started ASAP. But if you really want to be creating something new - VS living off the buying and selling of others - companies that make products and services - both large and small - are the place to go and go there now. Learn as much as you can about what really makes these companies successful. When hiring I'm a big believer that a great athlete is more important than someone who has N years of experience in a particular discipline. But that's only true when all other things are equal. If I can work with a great athlete who has spent 10 years in I-Banking and has therefore become the master of selling powerpoints and financial model assumptions or I can work with a great athlete who has been intimately involved with creating products and services that people actually want to use, it's not even a tossup. No matter how fancy the wall street resume, no matter how high the SAT scores (yes, some people still show them and some people still ask for them on their resume 10 years out of undergrad) or GPA, the person who is smart and also experienced in a directly relevant way is much more valuable. And the same applies for consultants - if you really want to create - do NOT become a consultant as your foundational experience out of college. Consultants are the 180 degree opposite of entrepreneurs and entrepreneurial companies BC they don't have to live with the consequences of their advice. Further, most startups are 10% strategy (or less) and 90% execution and consultants are some big percentage selling to clients to keep them happy and some other percentage - perhaps smaller - thinking up strategy; there is little to no execution in the mix. Don't get me wrong, strategy at a startup is incredibly important but if you can't actually execute on the strategy, the strategy is just a piece of paper.

I really like your point about the lure of the current hill. One thing I've observed in startups is the temptation of viewing the most important hill as the fundraising hill. Fundraising is hard and you get to talk with a lot of smart people (VCs) who may or may not validate you (risk and competition as the psychological urges). Further, the tech/startup press world writes about fundings as if they are an accomplishment onto themselves and the press often celebrates those companies that have raised a lot of money. The reason for this is because the press needs news and fundraising stories are news - it's not the presses problem 3 years down the road that the company is living with the high water mark 50M of invested capital. As an entrepreneur, it's important to realize that raising money is simply a means to an end. If you don't use that money to make a lot of money - you don't ever build value. And when the money raised is equity, it's money that is on your balance sheet forever - you can't ever pay it back and have it out of your life. Raising money is hard and it's often gating to growing a business but in and of itself, it means absolutely nothing. I've seen it become the "current hill" that you refer to and captivate an entrepreneur far more than it should. Every minute you spend raising money is a minute you don't spend being creative and building products that people want. That's an opportunity cost that has to be in the mix when you evaluate your fund raising strategy. A higher price that takes 6 additional months to get may not be worth it.

Ellie - great comment. The part that really struck a cord for me was about how entrepreneurs talk about the amount of capital that they have raised over their career as a badge of honor. As a former VC, it would internally bother me when an entrepreneur talks about how he has raised "$xMM in capital" (and normally the number is above $25MM). All that means to me, especially if they don't have the total $s achieved on exits, is that you have prior experience in burning through money. I never saw it, but I was always waiting for the CEO who came in and told me, in aggregate, that he has raised $3MM and exited for north of $50MM. That would be much more impressive than having raised huge amounts of capital. Anyway, off topic, but Chris that could be your next blog post (great job lately btw).

Great comment and great blog

This doesn't solve the inherent problem. How do I, nice student girl, who has 3 months left of classes in a non technical major, and suddenly realized this is where my life is going, get there. There are a number comments here about being sidetracked. Beyond these posts (which are really helpful), what steps do you take? That's hard. I don't know. What would that powerpoint look like?

Elie - Great comments. Particularly agree with your point about consultants and the not "liv[ing] with the consequences of their advice" (many of my friends are consultants, I'm an entrepreneur). However, I think we can extend this idea beyond the realm of consultants, and think of anyone who is not a founding entrepreneur.

Just as it is easy to give advice to others (but hard to follow your own "do as I say, not as I do"), it's very easy to spit-ball ideas for someone else. Whether it's friends, family, investors, etc - if they're not directly working on or invested in your company, their advice should be taken with a grain of salt.

You know your business better than anyone else. Don't let a stranger start you up the wrong hill.

Completely agreed.

Thanks Elie.

Looking at my comment again, I forgot the group of people we should listen to: our users.

Elie - as usual, agree with everything you say, and don't anything smart to add.

also, why do people think there is no entrepreneurism in finance? this is an absolute misnomer

I don't assume that. one of the entrepreneurs I admire the most is Mark Gerson, who started Gerson Lehrman Group, perhaps the most successful NYC startup this decade. when I say "finance" here I am using it as a proxy for "big financial firms." I should have been clearer about that.

Along with Warren Buffet, Ken Griffin, Paul Tudor Jones, David Einhorn, etc etc... the list goes on and on, but I should hope to assume that you include people like this in the mix as well? GLG is a poor example of what mark is referring to I think.

sure, agreed. i am talking about a junior guy at a major investment bank. if he goes and starts a new venture, i consider that a startup whether in finance or tech.

Presumably you speak from the top of the hill?

no, not at all. but i've found a hill I want to climb.

practice is important both for accomplishing your ultimate goal but also for getting the most out of it. i think climbing one or a few smaller hills might be excellent preparation for the big climb. meaning...nothing wrong w/ the short term/nearest small-hill climb, imo

yeah, i think it just depends on how much time you spend. 1 year at any quality institution in any industry is probably useful no matter what you do. beyond that, i'm not sure.

Chris,

I'm battling the same decision (although with Consulting not I-banking). My problem is finding quality startups that are willing to hiring individuals with a business finance/consulting background and 3 yrs experience. Founders seem to want technical experience only.

So then the question becomes: Is it better to take another step up the hill in consulting (or I-banking) and gain more business experience in the hopes a fatter resume will make you a more appealing candidate?

It's easy for we technical founders to undervalue the non-technical. Most of what we think about is solving the problem. If you can't directly contribute to that, you're facing an uphill battle to get into most technical startups early. You need to bring something to the table that has demonstrated value. Whether it's some deep industry experience/knowledge, great sales skills (proven carrying a big/tough book), killer strategy/planning, or product management (NOT project - very different). All of these are "non-technical" and can have a greater impact on young startup than most developers. If this wacky startup life is really what you want, find the way you can add value and jump in.

Allen's problem underlines a fundamental issue: it's much easier for tech people to pick-up financial concepts than vice-versa.

David
I agree to you completely on that point.

I think the only question you should ask yourself is "What do I want to do in 10 years?". If you aren't sure about the answer, go talk to people and try to learn. But don't waste time on jobs that don't get you closer to whatever that goal is, if you find it. (Took me many years to find it btw).

Also he should consider the fact that he has effectively bribed his employer to get the raise. His bosses are probably already looking for his replacement, knowing he will be gone in six months anyway. Co-workers now look at him knowing he got a raise (by resigning) and they didn't. What is the probability of getting the plum projects when the risk of him leaving is high.

He has shown his hand and now the best option is to move on. The longer he waits the harder it will be to move to a startup. This is a test. If he succumbs to the counter offer, then maybe he is not the startup type after all.

In my opinion, it's a little more complex than that. Yes, you risk bad blood by bringing in a competing offer (or even just a different career path). At the same time, most high-achieving employees are by definition under-valued at their current salary, which tends to be more of an average. It might not be as true for a trader, for example, but it's definitely true for a banking analyst or consultant. Bringing in a competing offer is just a way of arbitraging your way closer to your true value. It's somewhat risky, but every reward has its risk.

That's all a separate consideration from whether you're climbing the right hill in the first place.

I think in every other industry people think that way, but on wall street they might actually respect the fact that he bribed his way to get more money. And also that he responds to more money. They know that's the one motivator they have so need people who love money.

Given what it takes to work at a startup--something not everyone is cut out to do--I wonder if the siren's lure of the finance world is a myth. I know plenty of folks that have made that jump, as I did--and so when I hear someone hesitate, I wonder if maybe they don't *really* want to work at a startup. It may sound nice, but finance is comfortable, even if it's miserable--and a lot of people want comfort and security.

That's why I question a lot of the city's efforts to turn former bankers into entrepreneurs... There's a reason why someone agrees to work at Goldman and get treated like dirt--and if it's the money, working at a startup isn't quite going to solve that problem.

Now, one reason people do wind up here is the information problem that we tried to tackle at Path 101--that people know about finance because it's a recruiting machine. The way people see career paths early on is basically through job postings and little else. The tech world is very foggy--and not foggy because you don't know where the jobs will lead, but literally because you don't even know it exists. I grew up here in NYC and didn't realize there was a tech community here until 3 years *after* I graduated school.

Its funny that you say that you didn't know the tech world existed for so long. I also went to school and grad school in NYC. For me it was the exact opposite, I seem to have been blissfully unaware of the finance world until about 3 years after I graduated.

The finance industry seems like a very big deal right now, but before the industry blow-up last September, I had no idea how much the investment bankers were making, (and I don't think the other people that graduated with me did either).

I would have also said that what you might find behind the closed doors of the finance world was a complete mystery. Also the few investment bankers I met while I was going to school seemed utterly miserable. Tech seemed way more real. The idea of putting together a circuit or an electro-mechanical assembly felt more tangible.

In retrospect I wish I had known a little more about finance, and investment is definitely interesting in its own right, but I am glad that I chose to continue with robotics. Our own biases probably clouded the information that was available to us on alternate career choices for a reason I suppose.

I'd love to add my color on this, because I work @ a startup, and I want to go back to finance once I get the chance. My reasons are as follows:

1) Adding value to the world: a) most startups don't really, and b) it's just not that important to me right now. I care more about adding value to my family, monetarily, than I do to the world, at the moment. Being able to pay for my parents' retirement, my children's tuitions with ease, my extended family's needs, etc etc. Being valuable in this way is far more important to me, at least at the moment, than being valuable to everyone else, and I guess that is the bottom line for myself right now.

2) Enjoy finance: I genuinely enjoy looking @ and analyzing companies. I enjoy investing. I enjoy learning about different business models in different industries, and how they work. I enjoy the prospect of putting capital into those businesses, and earning a return. I like finance. The allure of being at a startup obfuscated this, for the past 2 years.

3) Getting wealthy: it's just quicker in finance. Less than a few percentage points of startups see any kind of exit, and of those, even fewer return anything meaningful (over a few million dollars) to their founders (let alone employees, which is what I am right now). I didn't realize this going in, but I sure am glad I realize this 2 years later.

4) I don't need to build value myself, to create value: I'd love to be a seed investor, in 10 years, when I've established some wealth independently. Not necessarily a principal investor, but I'd love to back established entrepreneurs, who are looking to raise capital to invest in good ideas (beyond their own). Reason being: I do care about creating value in this world, but not as much as I do, about creating value for myself, and my immediate significant others. Maybe it's because I'm not rich myself, by upbringing, and neither is my family. Whatever the reason, I have come to realize that this is my sentiment.

I've both encouraged, as well as discouraged, a few would-be tech entrepreneurs coming from finance, simply by giving them the reality: if you genuinely care about creating a new product that fits an underserved need, and selling that product, regardless of the comparatively low pay check that comes along with it (for most likely your entire life), then definitely join a startup. Otherwise, think twice.

Brad, that is an amazing comment.

As someone who spent well over ten years in (non-tech) finance, and is now living the dream, your comments resonated very strongly.

The key issue is this: if you're happy in what you're doing, you'll do it better. I was ok at selling stocks to institutional investors. I could have gone on and made a lifetime carrier out of it (and put my kids through college) but my liver would have exploded when I was 50.

Instead, I took what I learned from finance, combined it with my earlier tech ideas and created a business that can really make a difference.

I'm very happy with my life at the moment (apart from the money) but am very optimistic. My optimism is worth more to my kids than just being able to buy them whatever they want.

If you're happy in your finance job, then that's ok. If you're happier changing the world (whilst giving up some security) then that's ok too.

The key thing is to be happy.

David-
Awesome comment. I'd love to chat about your experience and your optimism sometime!

The conversation on this blog is better everyday!
Cheers,
Ryan

Thanks Ryan, happy to chat.

I'd agree finance is a faster and more likely way to get rich. I think my hill metaphor applies equally well in reverse (finance over startups).

yes, i think the analogy is a smart one either way. btw, great topic, thanks for bringing it up.

Hi Charlie - I also question the effort to turn bankers into entrepreneurs in the sense of 10 year banking veterans who have internalized the norms of wall street. But I think the kids out of college or 2 years out who are in NYC are prime candidates for the next wave of entrepreneurs here.

Agree also about the information problem. The startup world is murky - most information travels word of mouth and is in little pockets. That's one reason I was arguing for a nyc tech blog - which i believe you disagreed with me about ;)

Excellent post. I was in this guy's shoes 10 years ago and spent another 3 years in investment banking, which I regret. It's valuable basic training for finance and builds a strong corp dev network, particularly if you're in an appropriate industry group. The initial learning curve is steep but plateaus quickly. He should get out while he's young and can explore new opportunities with limited risk.

Yeah, probably the first year is useful in almost any industry but smart people tend to have significantly diminsihing returns in terms of inter-industry learning.

Hi Chris- I like the computer science analogy you give, this helps my analytical brain...., As a former Psychotherapist I can add another anology; This young man has chosen the hill he knows best. This is the safer option which his subconscious mind has directed him to pursue. Not necessarily the hill that will gethim the topmost vantage point but one which he feels more confident in climbing without falling in the shortest time frame. Did he make the right choice? Who knows?

In business so often it boils down to simple maths: opportunity vs risk. Your friend here has made the calculation that the total opportunity for joining a tech start up was less than the total risk involved. We can't fault him on that decision. If you're going to start up in business you must be convinced that the opportunity outweighs the risk.

Personally, I just get so bored with choosing the "safer option". Too many times in life I've chosen the perceived safer path only to find life has a funny way of surprising us. Regrettably, I've missed opportunities I should have acted on.

It's interesting here that the "safer" option is a job in finance. Come on folks!!!, in this economic environment how safe is any job, especially one related to finance? I would rather be in control of my own destiny than rely on the false assurances and prospects of a "safe" job in the city. In my view, there is no better time to start up in business than at the present time.

take care, David

Agree on all points. Especially that people over estimate riskiness of startups, see http://www.cdixon.org/?p=181=1

Thanks for that link to your blog back in May-that's a great article- we see eye to eye on this one.

Neat post! Yes, not mistaking the local maxima for the global is the key to hill climbing.

Nice. This is the first time I've seen simulated annealing being applied to careers. Makes sense.