The fifth annual Q&A. Or sixth. I can’t remember.

It's the fifth annual Penelope Trunk Q&A. It's not that I don't answer questions. I actually answer almost every question I receive. But only rarely in a blog post. The problem is that most questions suck. Look, here are posts about how to ask good questions.

In fact, I’ve been getting so ornery about questions sucking that I did a webinar about how to write a good blog post and I got pissed off in the middle because the questions were so bad that I walked off camera and half the video is Ryan Paugh telling me not to be a brat.

So, in the spirit of not being a brat, I am answering questions that I think are interesting.

Question 1: Your recent post about Lebron James really resonated with me. [Note: Making a reference to that post I wrote is good. It makes me like you because I like people who read my blog.] I too have been in the quagmire of “interesting” versus “happy.” I’ve decided to go the happiness route and head home to Kansas and settle down. But I'm not sure on how to approach the job situation. I can use a relative’s address on my resume, but I am working in New York so I am technically a non-local candidate to Kansas companies. And we all know how well that goes over with recruiters. [Note: I have written about this topic before. I know that she knows a long-distance job hunt is really hard, so I can't send her to that link, so I had to write a new response. I like when people have already done some research”?it usually helps them have a good question.] I can’t go without a job so it’s a difficult situation. Are there any strategies that are effective in handling this?

My answer: Say you are moving there in two months and in the mean time you are in Kansas every other week, getting things in order.

Something like that. So they don’t feel like they are relocating you. (This, of course, does not have to be true.)

And, good luck with the move back home.

Question 2: How do I become an evangelist? Is the most important thing to getting a good network? Do I need to first become an expert? What is the key to this career path?

My answer: I think a better question is why would you want this job? The highly paid evangelists have big travel schedules. And it’s a hard life. Most evangelists you can think of are people who are trying very hard to get away from that life of high travel. Seth Godin, for instance, focuses on writing and at this point takes (pretty much) only speaking engagements that are a one-day-round-trip flight. Guy Kawasaki is focusing on writing books and speaks only in California unless it is for tons of money. I got paid $15K a speech and traveled every week and would never go back to that life again. So the whole evangelist thing I think might be a myth, not a career anyone wants to sustain when they have it.

Sometimes I think I do not give practical answers. I am trying to be a more practical person. So here is actionable advice: Forget about being an evangelist. Work hard at knowing yourself and being kind to people. The right career path comes from that.

Question 3: [I'm paraphrasing a five paragraph email that was not as crass as my wording.] I'm 22 years old and I have a dream job, the kind everyone hopes for right after college. I love the job. I love my boss. But I also love this guy who is in the US Virgin Islands. I am in Baltimore. He makes a lot of money and I never get to date guys who will make more money than I will. Should I relocate?

My answer: Move for the guy. You can always get back on your feet. I’ve moved three times for a guy, giving up a great network and great job each time. It didn’t always work out with the guy, but I always get back on track with a great career. And I never regret moving. You’re young. You have so little to lose. And being in love is so fun.

[Then I wrote a second answer to her.]

I hate to sound like your mom but just listen: The Virgin Islands is known for really shady business deals. Be sure he’s an honest guy. Not that any of us is totally honest, but maybe hope that he’s in the top 30%. Don’t get kidnapped. Maybe do a background check. Not kidding. I did a background check on the farmer before I went to his farm for the third date. It's not paranoid, just practical.

Footnote to that last answer: For those of you who are naysayers about relocation for a guy, here is a photo that my ex-husband (who I relocated to NYC for) took on the farm (where I relocated for the current husband). It’s my son’s birthday, and we all had a great time, so following men, even if it’s not good for my career I think has been good for my life:

38 replies
  1. AlliG
    AlliG says:

    The most important lesson I have ever taken away from your blog is that if I’m not getting the response I want from others (raise, movement on a project, progress in a relationship, etc), it’s on me. It’s not the other person’s problem–even if they seem completely and insanely wrong. It’s on me to change the way I communicate and change the situation.

    Perhaps that same lesson applies to your approach to the questions you’re getting.

    P.S. Please blog more.

  2. DL
    DL says:

    1. I agree, please blog more. I miss your words.
    2. Love the red walls.
    3. To questioner #3, Yes, do a background check. You’re stupid if you do not. You’re giving up everything to move to the Virgin Islands, which is okay if the guy is right. But not okay, if you’re not sure.
    $. Your boys look happy.

  3. barbi
    barbi says:

    Actually I want to re-phrase my last stupid question. (my husband walked in on me and I felt guilty about sitting here NOT working so I hit the send button before I thought…)
    I really did love this blog, I love all your blogs, they inspire me with mine,so anyway I know all about stupid questions and comments…
    I do have a stupid question: I just noticed that all your guest bloggers are men. Why is that?

    (please delete my previous comment)

    • Penelope Trunk
      Penelope Trunk says:

      Wait. I can’t delete your previous comment. The two together are so funny. I also have times when I make everyone get away from me so that I can have time to work and then I don’t do the work I said I had to do. I love that you did it, too :)


  4. Penelope Trunk
    Penelope Trunk says:

    People ask that a lot. The list is just not updated. In fact, maybe I’ll update it today. Jamie Varon and Rebecca Thorman both wrote great guest posts.

    And now, a word to all the people who are going to ask about guest posting. I get asked every day about guest posting, and I’m open to it. But I’m a tough sell. Here’s what a guest post needs:

    1. A controversial opinion on a career-related topic. (Note that controversial is different than sensationalist. The point here is just to be interesting. If your ideas are not controversial then everyone has already thought of it and agrees with you and you’re preaching to the choir so why do it at all?)

    2. You have to give some sort of advice on how to have a good life.

    3. You must have expertise in the topic you are writing about. (Personal experience is fine. No degree necessary.)

    If you have an idea, send it to me before you write it so that you don’t end up writing something I won’t run.


  5. Bill Brent
    Bill Brent says:

    There seems to be a meta-theme here, and I think it’s an important one:

    We’re ALL missing out.

    For every choice we make, there’s at least one other choice — usually more than one — that we don’t get to make. Sometimes things don’t work out the way we hope, and sometimes the choices that seem like bad moves turn out better than we expect.

    Remembering this helps me to keep things in perspective.

  6. tiger
    tiger says:

    (i’m going to guess, just so as to avoid clumsy sex-indeterminate constructs, that questioner #3 is female.) when questioner #3 says she never dates guys who will make more money than she will, is that a complaint or a statement of personal policy? i’d need to know that before i could be sure how to answer her question, since in one case the guy’s (purported) income is a plus and in the other it’s a strike against him.

  7. Penelope Trunk
    Penelope Trunk says:

    Thanks for pointing that out. I made a little edit up there in the post to clarify: a lot of money is a good thing. (Who would not say a lot of money is a good thing anyway? I mean, you can’t make my list of smart questions if you are not smart enough to know that, all things being equal, having a lot of money is better than not having a lot of money.)


  8. pfj
    pfj says:

    The issue of money reminds me of an old saying. Well, I heard it a long time ago, that makes it old, right?

    “Money can’t buy happiness. People with eight million dollars are just as happy as people with ten million.”

  9. Emma
    Emma says:

    I’m going to put it out there that I don’t think moving for a guy is a good idea, if you’ve got a job you love, etc. If you’re questioning whether it’s a good idea (meaning you have your doubts), then you can live without following your guy to the Virgin Islands, and you will almost certainly be better off in the long run.

    I should add some caveats.

    #1: I do not believe in “soul mates.” This 22 year old will find someone else, probably someone better (she’s 22! I’m so glad I didn’t settle with my boyfriend at 22). This will probably happen even if she does move to the VI. But avoiding the move will allow her to keep her career and finances on track without dealing with the VI’s bizarre economy.

    #2: The whole discussion of money gives me the willies. Not because I don’t think it’s important to have money, but here it just seems strange. (I also don’t understand how a person doesn’t “get” the opportunity to date guys who make more than her. Go hang out at the Porsche dealership.)

  10. tiger
    tiger says:

    Well, the possibility *does* exist that a woman would rather make more money than her man, just as some men aren’t comfortable unless they make more money than their women. And there are those people who prefer a simple lifestyle to one whose maintenance requires a high income (and outgo). But then I suppose such people are not likely to read a blog called “Brazen Careerist”…despite the fact that they’d undoubtedly find much in it to interest them too.

  11. celi.a
    celi.a says:

    I usually just lurk here, but this post put a big smile on my face, so I wanted to thank you. Your advice is solid, and the photos are precious.

  12. Irv Podolsky
    Irv Podolsky says:

    Should a gal relocate to be with a guy? I have a story about that.

    I met a nurse when I was 25. I really, really, really connected with her. From the moment we found each other we talked and talked and talked (and did other stuff around the talking.) About 12 days into our joined-at-the-hips connection, I began to think, maybe I had a future with the nurse. But I was leaving for New York City in a few weeks to start a new life, a new career, a wild adventure. So when the nurse asked me if we’d stay in touch through letters once I moved, I said, “Well… No. Long distant relationships go nowhere.” The nurse cried. And then I knew, I should be crying with her. So a few days later I asked the nurse to come with me to the Big Apple and she said, “Irv, I’m not a camp follower.” I spent another 72 hours figuring out what she meant while we talked and talked and talked some more. So now it’s like, three and a half weeks into our relationship. It’s midnight, we’re sipping hot coco and munching iceberg lettuce with blue cheese dressing in a Waffle House. In five days I’ll be taking off, meaning, for the nurse and me, we’re facing a choice about ALL or NOTHING. I went for ALL and put a ring on her finger. She then said, “Yes, Irv. I want to marry you too. Where ever you go, I’ll go.” And she did.

    That was thirty-five years ago, and we’re still tremendously in love. But now in our sixties, we know we’re heading toward an eventual sad, sad separation. One of us will die first. We talk about that because we we don’t feel whole being apart anymore. But the nurse has stated more than once that she’ll wait for me. It’s a promise. And I have promised I will do the same for her, even if it means relocating to Heaven.


  13. Tzipporah
    Tzipporah says:

    “Work hard at knowing yourself and being kind to people. The right career path comes from that.”

    Thank you. This is the best advice I’ve gotten from anyone in a year. Seriously.

    Also – how great is it that your ex comes out to the farm for a kid’s birthday and you all have a good time together? For someone with social skills problems, you’re doing better than most of us at maintaining good relationships.

  14. Kristin
    Kristin says:

    Irv, your post made me cry. You and your wife are extremely lucky to have each other.

    My boyfriend relocated to my home city (Brooklyn) with nothing but a laptop and a few pairs of jeans and t-shirts to be with me, and now we are relocating to his home city (Austin) to continue our life together. Love is more important than any job.

  15. Irving Podolsky
    Irving Podolsky says:


    What I didn’t mention in the story, is that I was a waiter at that time, moving to New York to restart my movie career. When the nurse first asked me, “What do you do?” I answered with a hint of vanity, “I’m a filmmaker.”

    The nurse answered, “Filmmaker… Can you make a living at that?” And although I was a starving waiter at the time, she married me anyway. I will forever thank her for that. And I’m also grateful that today I’m no longer serving tables in restaurants, only my wife cappuccinos in bed.


  16. Mariane
    Mariane says:

    Dear Irv;

    thank you for sharing your wonderful story! I have found through listening to peoples life stories that the couples who started out in an adventurous way – and have kept it that way – are the most happiest, easygoing, fun, life-affirming and encouraging folks to have around. So: Well done!

    now, for that 22yo.
    completely agree with Penelopes advice. go girl, go…! and surely you have a whiff of what tier he is in regarding values. Just make sure they are on the right side of decent or you might be in for a nasty suprise. In any case keep some retreat money at the side;) as for career; well, if he is up and about there are a lot of lessons to be learned just by hanging out and listen…

    I have relocated a few times for a guy myself… it demands faith, courage and an adventurous mind – like Penelopes!

  17. Jonha @ Happiness
    Jonha @ Happiness says:


    I like it when you answer questions or talk in general about love, being in love and simple believing in the power of love. It makes you more human, more real and more genuine (just as you already are)

  18. carak
    carak says:

    Penelope: I love your blog and your advice. Particularly like your answer to Q3. Both answers. I’ve relocated for my husband and couldn’t agree more.

    On a related topic, I feel that so many times in the business world, particularly for women who hold upper management positions (read: my bosses), they expect you to make a choice that is either family or career. I've found very few managers who value both. It's an issue I struggle with, and it's unfortunate because women in senior management have the power to change the perceptions, but (in my experience) they've only reinforced the division. Makes me want to start my own business.

    I really appreciate that you give career advice while also addressing the reality that is personal life, relationships, love, family, etc.

  19. Missa
    Missa says:

    Thanks a lot Irv… You made me nearly shed a tear at my desk. This comment should have the disclaimer, “Do not read if you are 37 weeks pregnant and totally in love with your husband”.

  20. Sean Masters
    Sean Masters says:

    Have to jump in on the relocation discussion. A few years ago, I relocated to follow my girlfriend at the time as she got a can’t-pass-this-up job offer on the other side of the country. I found a job (using the tried-and-true “I’m relocating myself by the end of the month” line, which wound up being true anyway), moved out to be with her, and we split up 3 weeks later.

    Not a day goes by that I regret my decision to follow her. The job was amazing, the co-workers and connections I made were fantastic, the friends and dates and all of the other experiences I had throughout that 22 month stretch were spectacular.

    I wound up moving back across the country for my current job, which leads me to my second point: the money won’t always follow you (the Pac NW IT market was hit insanely hard at the end of 2008), so make sure you’re able to follow the money ;)

  21. Christy
    Christy says:

    Ha ha, I totally read question #2 as a guy who wants to be a televangelist. You could just start out with YouTube videos these days, right?

    Also, question #3, if you uproot yourself and move to the VI then make sure you can be totally independent if you have to be. In case he turns out to be a douchebag in the first five days and you decide you either want to get the hell outta there or give the place a try on your own.

  22. Mark W.
    Mark W. says:

    I’m thinking one or more of your posts on asking good questions belongs on the /rants page of this blog.
    I liked your blog post(s) on how to ask good questions and I liked Seth Godin’s approach as discussed in your webinar with him to answering questions – good or bad.
    I wondered at first why you included the first photo of your son carrying the cake since it was so blurry. However, as blurry as that photo is, it’s evident how excited he is to get it to the table and get on with his birthday celebration!

  23. Michelle Drea
    Michelle Drea says:

    This topic is endlessly fascinating. When to jump and when to stay? I left a dream job to move across the country and become an unemployed wife and stepmom. My brood has since grown by two…leaving me with the four loves of my life. No more dream jobs so far…but I wouldn’t change a single thing. Not only did the jump allow me to redefine myself…risk taking is important to feel alive (risk taking with background checks to stay alive…of course).

  24. John Carraway
    John Carraway says:

    I found your points about evangelists to be very honest and truthful. Not many people with a family want to be on the road most days of the week. Also, most experts aren’t really experts, they’re really just marketers. Even when evangelists are supposed to be experts on marketing, they’re really just experts on marketing themselves and not much else. But I guess it helps them push their latest books, trinkets and wares.

  25. betty in munich
    betty in munich says:

    Here’s my move for a romance story (I can’t top Irv!). In 1999 I was just finishing a 2 year ex-pat contract working for a german car company in Munich. I had just started dating one of my german colleagues and thought I would be able to extend my contract. Instead, I was offered a great job (with same company) to return back to the USA. It was such a great job it made my head spin. The romance on the other hand was just starting. What to do? I called my mom, fully expecting her to say don’t be silly go for the great job. Instead she said, you are so talented you can get a great job anywhere – Love…that’s not so easy to find. So I stayed in Munich for the new romance. Penelope and my mom were right. I found a great job with another big german company and went local so to speak. The romance? Still going strong! My advice, if you do decide to move for a partner, make sure your finances are in order and you can land on your own two feet if things don’t work out. I always kept a back up savings plan that I didn’t touch just in case I found myself having to relocate etc.

  26. Sarah
    Sarah says:

    As far as the moving girl goes?

    Kind of sounds like she loves him for the money. She should go ahead and move, and once the guy and all his money are gone, maybe then she’ll re-evaluate what’s actually important in life.

  27. Jovit @ Sytek MN Directory
    Jovit @ Sytek MN Directory says:

    @Irv That was a touching story.

    @Penelope You know what I like about reading your blog, its the way you “talk” to us. Anyway, the 22year-old girl doesn’t seem to be in love with the guy indeed. I don’t want to judge her but based on what she said that she never get to date a man who makes more money than she does, it sounds like the man is a good opportunity for her that she doesn’t want to lose.

  28. Annabel Candy, Get In the Hot Spot
    Annabel Candy, Get In the Hot Spot says:

    Oooh, I love this. I think my dream job would to be an agony aunt and answer all people’s questions to help them solve their problems. The only thing is that some people do not listen to advice no matter how good it is and even though they asked for it! But some do. I suppose we all have to follow our intuition in the end. My son turns 9 tomorrow. The cake is made, the candles will be blazing:)

  29. Elizabeth Harper
    Elizabeth Harper says:

    I left my whole life, a home, career, friends, and family and moved to another country because I fell in love with a British man. It was the best and easiest decision I ever made. Plus, during our early courtship I was offered an amazing job by a company that contacted me. I made the decision follow my heart only eight weeks after we met online. Almost three years after our first meeting, we’re married and he’s even more wonderful than when we first met.

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