Welcome, San Francisco Chronicle readers


It looks like a lot of people are coming here from the article in the San Francisco Chronicle: Big City Blues, Could a more affordable life, away from the Bay Area, actually be better, by Rob Baedeker.

Here are some of my most popular posts about figuring out where to live:

Also, when I moved to Madison, I founded the company Brazen Careerist, which is funded by investor groups in Madison, WI and Washington, DC. Then I wrote this post:

Starting a company in Silicon Valley is stupid

Thanks for stopping by, and I hope you enjoy the blog!


24 replies
  1. prklypr
    prklypr says:

    “I feel like if I just stay in Wisconsin, if I just stick out, then somehow … I’ll just stop being a maximizer. I kind of already see it. I’m in jeans that don’t really fit right now. I buy my coffee at the gas station. Each day there are little things.”
    I don’t get this. The fit of your jeans is somehow an accomplishment? Or am I misreading this sentence? Did you mean: I’m in jeans that don’t really fit, right now…or… I’m in jeans that don’t really fit right, now.
    Either way, what does the fit your jeans have to do with anything??

    • Penelope Trunk
      Penelope Trunk says:

      People in Wisconsin don’t pay $300 to get jeans that fit perfectly. And no one would notice, anyway. In cities where people pay this much for jeans, people notice if you are wearing cheap jeans — they can recognize a bad fit.


      • Barry Adams
        Barry Adams says:


        Are you ok? Should we start a fundriaser for you so you don’t have to mingle with us who buy our coffee at the gas station? Since when is paying $3 for a cup of Joe a good thing?

        Being happy isn’t a competition. It’s a state of mind that is personal.


  2. Angel Vallejo
    Angel Vallejo says:

    It is amazing to see how most people are terrified about moving to a different place. It is specially amazing with people that have previously moved out of their hometown and have succeeded in their new life/town/job.

    Unless you do something totally linked to an asset fixed to the land, technology allows you to move to almost everywhere.

    However, all of us seriously doubt we shall be even able to survive. Why is it like that?

  3. William Bruce
    William Bruce says:

    Since this issue of “optimization” is quite germane to the general conversation, I will (finally) drag out the intellectual architecture for an argument along those lines. Do pardon my rather rambling diction, on account of the nicotine and caffeine inducing this comment…

    To put the question to Ms. Trunk, why should the truth of the “optimizer” paradigm be repeatedly asserted when the entire conception of someone being such an “optimizer” is premised on an overly simplistic dichotomy?

    In these treatments, it is being presented as a vertical binary, and not a multi-dimensional paradigm. However, there is literally no such thing as a through and through “optimizer”; whatever is optimized is done so at the expense of another thing. That is the horizontal dimension in play here, among other things — with the added problem of actually determining which way is “up.” And all of this is true even in the more limited sense of optimization as materialism. Not only can one not have the best of everything, not only could one never possibly attend to the best of everything, but one could not even be aware of what *is* the best of anything (and certainly not everything).

    There may be, in this paradigm, a certain psychological insight regarding a particular class of people who exhibit certain behaviors, but to actually assume that there is any (or much) validity to their conception of “optimization” is to engage is precariously unsound reasoning. This could all be a vindication of American Psycho as much as it is the live-and-let-live, non-judgmental pluralism espoused by Ms. Trunk.

    Already addressing the issue generally, I may as well do so anecdotally: If anyone reports (especially self-reports!) optimization to me, I ask what it is that is being optimized, and how it is measured against other costs and benefits. I have yet to see the idea defended in a semantically rigorous way, although I would be happy to be shown up.

    Please forgive any false Socratic humility in my own assertion, but I cannot, with all my faculties, understand how the richness and daunting complexity of human values could be so gravitationally reduced to “optimzed” or “some-level-of-unoptimzed.” In this semantic context, “good” and “bad” truly are primitive notions — the common assertion of perspectivalists.

    But, as always, I humbly await refutation…

  4. TwistedByKnaves
    TwistedByKnaves says:

    William, try this TED talk for five dimensions you might want to optimise. http://is.gd/5fKi9- .

    Obviously each of us needs to decide on our own weightings and trade-offs. But it seems to me to be reasonable to strive to be somewhere on the envelope, rather than slobbing around aimlessly.

    As always, do what I say, not what I do.

    Hope this helps.

    • Brian H
      Brian H says:

      Bob, I think Penelope was being facetious. But in all seriousness, she has a point. I work for a non-profit and my SO is in grad-school. We just bought our first house. Granted it is 850 sq feet, but this would have been unimaginable had we stayed on the East coast. In Madison our situation is not unique.

  5. mktggrrl
    mktggrrl says:

    This is so true. I am a former mid-Westerner who relocated to San Francisco. I love this city and my life here but figure at some time I will need to “grow up” and that may mean relocating somewhere more livable. However, that same complacency about certain parts of the midWest bothers me as well. There has to be a happy medium somewhere…

    • Cheryl Morris
      Cheryl Morris says:

      I suggest that you read the book “The Nine Nations of North America” to get a feel for the different regional cultures that exist. The book is old, but I think it’s still valid (I’ve lived in Maryland, Texas, Colorado, Hawaii, New York State, and I agreed with the book’s description of regional cultures).

  6. Sean
    Sean says:

    Can I give you some advice? I like you, and I like the fact you moved her to Wisconsin. You can call me a friend ;)
    My first observation is that you have not fully committed to being here, and actually becoming a Madisonian or Wisconsinite. I don’t say you have to forget your roots, but give yourself permission to be ok with it. Jump in the pool. Embrace it, own it. It is a great place with great people. Who are smart, funny, attractive, and many of us look good in cheap jeans. We are not like the rest of the country. And we like it that way. Kinda like the old TV show “Northern Exposure”

    There is power in accepting who you are. There is also comfort and peace. Accept who (and where) you are in your life right now. The good, bad, exceptional, crazy. If you do, I think you will find that happiness in life will come to you.

    Let go. It is great on the other side!

  7. rufusmcbufus
    rufusmcbufus says:

    I’m not getting the whole Madison pool vs New York pool problem. Madison is a lake town. Lakes are awesome. Pools are sterile bore-fests. I pity the poor New Yorkers in their stupid tubs.

  8. rufusmcbufus
    rufusmcbufus says:

    Oh, and another thing…”Maximizers”. I’m a third kind of person. I completely “get” what Maximizers seem to think they want but KNOW (yes KNOW) they are on a fools errand. Don’t know what you’d like to call us, but there is nothing in the world (seriously I live for this) I enjoy more than watching a “Maximizer” crash and burn while attempting to “Maximanize the the Xtreme Paradigm of Multi-Networked Pro-activity” or whatever you types are calling it these days. Please continue to keep us entertained.

  9. rufusmcbufus
    rufusmcbufus says:

    Ok, final thing. You want to feel good about Madison? Just drive 90 miles south to Rockford, IL and spend a week there. Afterwards you will see Madison as an enlightened dream-land of culture and oppurtunity.

  10. Nick
    Nick says:

    I never got the fear of moving. If I have stayed too long in one place I always get itchy feet to try somewhere new. But that’s just me…

  11. Atniz
    Atniz says:

    Nice tips for moving. Also about starting a new company. You are very lucky to get a investor for a new company that you started in a new place. It is not easy to convince investors especially for online business.

Comments are closed.