Are you a cross-trainer or a dilettante?

I told Melissa that black and white photos look stupid on my blog.

Did you know Melissa edits my photos? It started out that she lived with me, and she took all the photos. Her photos are gorgeous. When she moved out of my house I knew I couldn’t take pictures as well as she did, so I asked James Maher to take photos. He brought a gritty street photographer’s eye to the blog.

James specializes in street photography. He cross-trains by taking pictures of me and my kids. He makes us look much more gritty and edgy than I feel. (Actually I feel gritty but not like art-project so much as shower-project.)

If he took pictures of us like we are in a sitting at JC Penney it would be bad for his career–because it’s outside his specialty. It’s always a fine line between helping your cause or hurting your career when you try a wide range of things. Here are three questions to help you figure that out.

1. Do you have a specialty?

But eventually, I had to start taking pictures myself. I hesitated, though, because I’m an expert writer, not an expert photographer. I told Melissa my pictures look dumb and she said I should just take a bazillion pictures and she’ll edit the ones that are good.

When the piano delivery truck came, I saw my son was using their trolley as a skateboard. I had him skate through this frame forty times til I got a good shot.

I thought maybe it was lame that I have to take so many pictures to get one good one, but the truth is that I have to write a lot of blog posts to get one good one as well. So I decided I could take my approach for writing and apply it to photography.

I found that the photos helped me write posts. When I like a picture, I am more excited to write the story. So much so that the only reason to tell you about the day our new piano came because I got this picture of how happy my son was.

Melissa said, “That’s a great photo.”

It means a lot to me when she says that. I’ve had an editor for the last twenty-five years. I never publish something unedited. So I’m keenly aware of the importance of a second eye.

Then when I got the pictures back from her I said, “Why are they in black and white? That’s so pretentious.”

“They’re good in black and white.”

“I’m a writer not a photographer. I can’t act like they are so precious.”

“Right. You’re a writer. So just trust me. The photos should be in black and white.”

I said fine. Because she’s right.

2. Are you addressing specific needs? 

I have the same issues with my son playing piano. He practices an hour a day even though it is not his primary instrument. You know those kids who do ten different things after school each week and they will never be really good at any one thing? I worry he’ll be that.

I coach so many people who spent their 20s doing lots of things. It’s fine, really though, because everyone has to do lots of things to figure out what works. But at some point, you have to examine why you don’t find anything you love doing.

Common reasons why people get to their 30s without finding anything they love doing: They are scared to commit to something: they don’t care about money enough to get to work every day, they don’t trust themselves to choose what’s right.

It’s not good if you can’t choose what you want to do by the time you’re 30. Because for women, it’s time to have kids. It’s pretty much too late to start looking for a career in your 30s if you want to have kids in your 30s. I mean, who has ever worked 12 hour days to establish themselves in a career while they have a newborn, right?

But it’s a problem for men, too. Because people don’t like hiring dilettantes, which is what you look like if you have not found what you want to do by the time you’re 30. Luckily, you can hire a resume writer to fix your resume so you look like you are cross-trained with a specialty rather than a dilettante with no focus. In fact, most resumes that I rewrite fall under this category: someone ends up being unemployable because they have done too many different types of jobs and I have to fix the resume to look like they knew what they were doing all along.

The way I make sure my photography isn’t dilettantism is that I don’t take pictures for anything except my blog. (Side benefit: I write on my homeschool blog four times a week because otherwise I won’t have a visual record of my kid’s lives. It’s a great motivator for me to practice my specialty.)

3. Are you choosing new ways to learn?

The first thing my son played, before the movers even brought the bench, was a scale.

Because he’s focused on the parts of playing the piano that will help him with cello.

To me, he is the ultimate cross-trainer. He is good enough at piano that he was able to get a teacher who requires auditions, but he realizes that if he doesn’t focus hard on the instrument he’s best at, then he won’t have a chance to be great.

I meet adults who don’t understand this concept as well as my nine-year-old does. He knows the odds are completely against him that he will be a famous cellist. But he also knows that he’ll never have a chance at greatness if he doesn’t have clear focus. Playing piano, he knows, is a way to better understand the music he plays on his cello.

Cross-training is essential for greatness—it is a completely new way to approach the specialty you are learning. And, Noa Kageyama points out that if cross-training is a great way to alleviate anxiety about your specialty. But if you get far-afield and forget the purpose of the cross-training, you could end up in the time-wasting dilettante arena.

Ask yourself how you reacted to that paragraph. If it bothered you, if you said “people should be able to learn a wide range of things,” remember that greatness comes from a combination of hyper-focus and careful cross-training. If you are constantly learning in the same way, it’s like constantly lifting weights the same way: benefits start to diminish. But if you are aiming to be a faster runner and you get obsessed with your arms, you are losing the benefits of building whole-body strength to promote fast legs.

There’s an article in the New Yorker about Carl Haber, a physicist at Berkeley who started investigating how to listen to outdated, unplayable recordings, like Alexander Graham Bell’s. Colleagues in his lab thought he was nuts to be thinking about something so weird and unrelated to his specialty. But what’s interesting to me is that he was already at Berkeley, at the top of his field, so his investigating into reproducing sound was cross-training rather than dilettantism, and it got him a MacArthur grant.

I let my son test pianos and he picked a Steinway baby grand. At first I worried that I’m an insane person spending so much money on a piano but this picture is when I realized I got my money’s worth: The piano is like art in my house that stands as a metaphor for how much I believe in focus, and specializing, and cross-training with purpose. I’m happy I took a picture because I’m not sure I would have noticed that moment.

48 replies
  1. Cyndi
    Cyndi says:

    Excellent, insightful article but I have a question. What happens if you reach your 30’s, have disciplined yourself enough to have worked in the same field (business operations) and acquired more responsiblity and pay with each transition, yet you still don’t know what you want to do? At 31, I find myself very unhappy with my job. I’m currently reading “Finding Your Own North Star” by Martha Beck. I’m really putting out a concerted effort to change the things I don’t like about my work life. I don’t want to have kids so that’s not really an issue. Your post today is striking at the heart of what I’ve been thinking myself. Thanks for sharing! And by the way, the photo of the piano with your son playing is really cool.

    • Barry
      Barry says:

      I really liked Find Your Own North Star. I also suggest Brene Brown’s book, The Gift of Imperfection. But the best is Fail Fast, Fail Often. I love it and highly recommend it. Good luck.

    • Stephanie
      Stephanie says:

      Echoing your sentiment. I’m 33 and have been on a path of healthcare sales and marketing since my first job as a pharma rep out of school. It has been a wonderful career for having kids, but not for mental growth and challenge. When I drop them off at daycare and I reflect on is what I’m doing a good enough reason to leave them? The only thing I can think of as a positive is the money, which doesn’t really feel good.
      So what next? I’ve read the Martha Beck book too, a long with a zillion others. It seems as if there are two camps, one side saying to get a portfolio career and try a bunch of different things
      . The other side says to specialize and get laser focused in on one thing. Adding cross training to specialization sounds like a really great solution between the two.
      I’d also recommend Choose Yourself by James Altucher. That’s one I keep going back to.

  2. C.A. Lewis-McCarren
    C.A. Lewis-McCarren says:

    I happen to like your raw pictures. Beauty is where you look – and real beauty comes from real life. So I’m just going the simple route and enjoying your captured moments as they happen – not pick them apart.

    Oh, and you INVESTED in that piano… didn’t spend too much. It is beautiful too.

  3. Grace Miles
    Grace Miles says:

    Penelope, I’ve said this about a few of your articles, but I love this. The idea of training in piano is practically a standard to string players but no one ever calls it “cross training.”

    The last photo is extra fantastic– the saying, “Our character is what we do when we think no one is looking” should be applied to passion as well.

    It’s interesting how he picked a Steinway baby grand and the metaphor it stands for you; I read an article about how in China, Steinways are popular status symbols ( and you just destroyed that– anyone who bought a Steinway as a status symbol should read your article.


    P.S. Your link to the JC Penney sitting is broken.

    • Penelope Trunk
      Penelope Trunk says:

      Thanks for pointing out the link, Grace. I fixed it. And it’s such a great link. A chic-chic high-art photographer went undercover as a JCPenney portrait photographer.


    • layla bb solms
      layla bb solms says:

      i was told to and did learn piano to help with my violin playing, though i’ve let both fall to the wayside. i suck at the piano. i can’t accompany anyone else to save my life.

  4. Lara
    Lara says:

    WOW! Love the last photo. The piano looks gorgeous in your home and your son loves it! Well done. Melissa was right… Black and white.

  5. Kim Leggatt
    Kim Leggatt says:

    Excellent photos you should take more – at the end of the day you’re the best person to photograph your life – only you know what truly matters to you and that’s what readers care about.

  6. Kathy Donchak
    Kathy Donchak says:

    I found my specialty way after my 30s in my 40s, and have decided after reading this post that I am going to remind myself daily that I found it. I just kept thinking if Julia Child could do it, so could too.

    I too read Martha Becks book, Finding Your North Star on my own personal road to finding my best work. I find that posts like these and her books are the stepping stones getting those that need a nudge a little closer to their answer.
    Your photos help us feel as if we were there in that very moment.

  7. Jana
    Jana says:

    What do you do when you had two kids by 30 after getting your degree. And now they are adults and your degree. Marketing. Is outdated and useless? I should be enjoying retirement but I feel unproductive and lost not knowing what to do?

    • Penelope Trunk
      Penelope Trunk says:

      Maybe you can console yourself with the fact that anyone who got their degree in marketing even five years ago has all outdated information.

      A degree in marketing doesn’t real mean anything in the workplace. Experience does. And you can get experience by teaching yourself. Using social media, using online brands, etc.

      Marketing is moving online fast and online marketing is changing fast. In order to do marketing today you have to maintain a very high learning curve… Actually I think this is true of any field that is growing. You need to learn fast and you need to be able to teach yourself.

      So really, Jana, you should feel better that you’re in the same spot everyone else is in terms of having to learn on your own. The only thing that’s stopping you is you.


  8. Jacque
    Jacque says:

    B&W are my favorite, so of course I am biased about these. I also like your photos as much as Melissa’s, but it’s great that you have her to edit and give feedback.

    Last week, someone made me feel really good for the first time ever about being 46 and barely being a step beyond an administrative assistant. She said she didn’t regret not being further along in a career, because the time spent at home raising her kids was invaluable. I didn’t get to stay home the whole time, but I did make work choices that cornered me in the admin asst. realm so that I could be home with my daughter and not have her in daycare 10 hours a day with no parents. It felt good to hear my daughter say that she remembered me being mostly there as opposed to absent.

    Meanwhile, I am 46 with college degrees in liberal arts and a mass of student loans. Still don’t know. Still stuck in admin world and watching my potential as it turns into a raisin. I get this post. Completely get it. But, it still makes me sad.

  9. Jim Grey
    Jim Grey says:

    But what if I don’t want to be the best at something? What if I just want to pursue a handful of things and enjoy the process of discovery and learning and growing? That’s what I do with my writing and my photography. The journey is fun.

    I’ve mastered skills around what I do for a living after 25 years of doing it. That journey isn’t as much fun anymore.

    • Penelope Trunk
      Penelope Trunk says:

      I dunno. It’s hard for me to understand, frankly – to be okay being mediocre at everything.

      Also, I have found that I force myself to grow at a more profound level when I force myself to stick with something and learn more. Go deeper. If you go deeper with knowledge you go deeper into yourself, and that’s interesting to me.

      Being a dilettante is like going on 1000 first dates.


      • Jim Grey
        Jim Grey says:

        Hm, I think we’re more on the same page than I thought. These are no first dates I’m on. I’m going deeper in these areas and therefore deeper into myself and I am loving it. I think the difference is that I’m enjoying the process and not thinking much about whether I’m going to be great at it. Perhaps being great at these things will just happen.

  10. Logan
    Logan says:

    In our current technocratic era, the US market doesn’t value generalists as much as we value specialists.

    Generalists are the people who start companies (if they find the right resources), whose vision inspires others, who can wear many hats, but during the expansion stage of a company, specialists become more valuable.

    Generalists are also the liberal arts majors who became displaced when their dreams of a secure job were dashed by the fast-moving financial and technology companies that required yes-men/ yes-women idiot savants.

    Highly specialised people are an asset, but our market moves at a fast pace, and people who do not keep up their skills become obsolete. A lot of people in their 30s find that they went into their careers for the wrong reason: money. It’s not that they cared enough about money, it’s that money blinded them from finding their true calling. That is why we have so many unemployed and displaced lawyers and software engineers in our society.

    Also, Penelope, since you are in the start-up space, you’re probably aware that most people who start companies are in their 40s and 50s. Sure, we have scant numbers of college kids who had the luxury of going to Stanford, Harvard and MIT, and drew the attention of VCs in those areas, but the vast majority of people who start companies do it after they have explored other career options and have insights and experiences that trump specialised skills.

    Women are brainwashed into thinking we need to have children by age 30. There are many reasons for this, which I won’t go into here, but a lot of the reasons why women become infertile in their 30s is due to the overuse of birth control pills that send their ovaries into hyperdrive, into premature aging. Back in the good ol’ days of the 1700s/1800s, women had up to 7-12 children, and bore them successfully into their 40s. That was the norm then, but our society wants to tell us that as women, we are over the hill at 30, when really that is where life really begins.

    Who knew what they wanted to do at 21? We graduated university, and blindly fell into a career because we were promised a 60K starting salary, without having experienced life, of knowing what we wanted to do, but that our life goal was to work for some corporate giant and buy houses that banks would eventually own if we missed one payment.

    Women got suckered into thinking they had to have a child by 30, when they didn’t really want one because they were busy with their careers and never found the right guy. So I disagree with you that we need to be settled at 30. People in the post-war era thought we had to be settled by 30. I know lots of women who have defied that contemporary norm, but rarely do we hear about them in the news.

    • Sam
      Sam says:

      From a physiological perspective it is not the same thing to have your first child at 40 as having your third child at 40.

      The first “generalist” you describe sounds like a visionary specialist. I’m prepared to bet that they need to team up with someone who can plan and execute things if there is ever going to be a product from the company they started. This is exactly the strategy Penelope states she has used.

      The second type of generalist that you describe sounds like someone who is a pain to work with and who lacks any other redeeming properties. Penelope has written a number of blog posts on being likeable and they are all well worth a read.

      The reason I recognise someone who is a pain to work with is because I am a pain to work with myself. I relentlessly keep pushing and always ask for more. People tolerate that to a greater extent since their work turns out pretty OK in the end and I expect no less from myself.

      I’m a specialist and I’m reluctant to the idea that skills constantly need to be updated for people to not become obsolete. Most new things are variations of old things and not something fundamentally new. Let’s take Penelope as an example: one of her specialities is writing about career-related things. How much training will she need to be able to write about home schooling? What are the chances she would miserably fail at the second thing if she is successful at the first thing? I realise that typical job adverts would ask for five years of experience in writing about home schooling, but she’d still kick ass in that job. I would not be surprised for a second if she was turned down for such a job though; companies seem to want someone who has done exactly the same thing for the past years. I find that puzzling given that jobs change over time, so it would make sense to employ someone who can adapt to the new situation.

      • Logan
        Logan says:

        Hi Sam,

        We already have a word for “visionary specialists,” they’re called ophthalmologists…I honestly don’t think when people decide to start a company, say to each other, “hey, we need a visionary specialist” ;) no, they prefer to go by “Co-Founder.”

        But don’t get me wrong, just because I’m not a gushing sycophant doesn’t mean I don’t like Penelope. There’s something so satisfying about reading her blog, even if I happen to think differently on many issues that she brings up. She’s a bit like Selina Meyer on VEEP.

        I suppose the problem with most job adverts and recruitment specialists (who are mainly female) is that they favour men over women, period. There’s nothing that infuriates a female HR manager than a woman she immediately loathes and feel jealous of when reading the résumé of a candidate that she wants to be like. “How come these women are doing exciting things with their lives when I’m stuck as a low-level employee for this faceless organisation for life?” So they choose men instead. But we also all know that HR people would never have hired any Co-Founders when they were young, not only because Co-Founders most often have the “outlier” personality that HR Managers hate, but also because Co-Founders often decide to launch their own business, and Co-Founders know never to connect to any organisation via the HR manager, but directly with the CEO.

        Let’s also remember that the specialists we had in the post-war era used to simply go by “factory worker.” They were all specialised to do exactly one thing. But we all know what happened to those jobs.

        When companies such as Google’s acquired DeepMind replaces software engineers with humanoid robots in the next 50 years, what do you suppose will happen to these specialised engineering jobs?

        But you bring up an important point, that adaptability is the key to survival. And that is one of the reasons why I also like reading Tim Ferris books.

        • Sam
          Sam says:

          HR departments seem uniquely dysfunctional in the US, but the rest of the world are racing to reach the same level of madness. I don’t think it’s just a matter of staffing or gender–discrimination against women is pervasive in our society and it’s both women and men who discriminate.

          Calling an assembly line worker for a specialist contradicts my understanding of the word. My dictionary says a specialist is a person who is highly skilled in a specific and restricted field. I agree that assembling the left front door on a car all day is highly specialised but I question whether that task is complicated enough to distinguish people who are highly skilled at it.

          Since I’m an engineer and know a bit about software engineering. I can tell that it’s not at all like engineering. Maybe 50 years is enough for replacing humans in those positions, but I’m not convinced. The first problem is that we don’t really understand human brains. Even if we did understand human brains, that knowledge would still have to be transferred into a working computer program.

          Researchers have been touting general AI since the 50’s and while there has been tremendous progress we are still nowhere near the point where a computer can take a partially defined problem and tell us the solution we are looking for. The current state of the art is that computers can verify that carefully written programs on special forms do not violate a mathematically rigid specification. Generating a program from a less detailed specification is still at the level where the computer would not pass the first year programming course.

          *If* Google manages to replace its own workers with computers within 50 years those capable workers will do something else. I see people talking to their watches today but I don’t see the flying cars outside my window, so us guessing about the job market in 50 years is just random guesses.

          • Penelope Trunk
            Penelope Trunk says:

            Sam and Logan, people are always telling me that I need a voting system in my comments section so that we can give a thumbs up. I don’t add that because you can only do it with software that makes you log in. (Wait: can someone find a solution to this???) But anyway, today is the day that I, too, clamor for a thumbs-up button so I can tell you guys how much I appreciate this conversation between the two of you. So much insight.


          • Logan
            Logan says:

            No, it’s not a random guess. Singularity is an ongoing movement. I’m not an expert on Singularity myself, but this is a book you might be interested in:


            I think you’re coming from a skeptical POV that the human mind cannot be known. I tend to take the position that it can. AI from the 50s can do simple tasks that surpass human intelligence: playing chess for example. Financial firms are heavily dependent on trading algos. I think our technology has far surpassed those binary decision making AI machines, and we are moving towards a more advanced species of AI that may not be readily visible within consumer spaces.

            In terms of specialists, I think you are moving towards an argument in semantics. Can you assemble a car door from scratch? I don’t particularly think writing code is difficult either. How hard is it to understand C++, Python, Ruby et al that we can’t program a computer to do? AI can do much more complex jobs: navigating warheads and assimilating thought control. We choose not to replace software engineers with AI at this current time, because our economy is driven by technology companies.

          • Sam
            Sam says:

            I said we don’t understand the human brain today. I also said that even if we did understand it we would still need to translate that knowledge into a working computer program. I’m convinced we will understand the human brain some day, but I have no idea when that day will be.

            It was in 1997 that someone had written a computer chess game that beat Kasparov, which is roughly 40 years after the 50’s. Chess is a structured problem so conceptually the computer can enumerate all possible moves in the next step, all possible countermoves to all the possible next moves and so on. That’s a huge search space even for a computer. The programmer reduces the search space by making sure that entire branches that are outright bad/not very promising are eliminated early. Another trick for speeding up the search is to exploit symmetry in the search space. The endgame in chess is fully analysed with databases available containing the best moves.

            Compare this to Go which is also a board game that the wikipedia page takes a couple of pages to explain the rules for. There are no computer games that play at the level of the best go players. Playing board games is still a restricted scenario compared to programming in general.

            I’m not sure if I could assemble a car door from scratch since I’ve never tried it. I could write a C++ compiler from scratch though.

            Your notion of what hard means is interesting given the amount of evidence that software is buggy. Why do we (humans, including NASA) keep making things that don’t work if it’s not hard? There’s even a wikipedia page called “List of software bugs”. Both (american) lives (MIM104-Patriot, 1991, 28 dead) and money (Ariane 5, 1996, $1 billion) could have been saved if the software had been working.

            Controlling a warhead consists of two tasks that by now are well understood. The first is to keep the rocket from rolling over and crashing into the ground right now and for that we use established control theory. The second task is to figure out the relative position of the rocket compared to the target. Figuring out where we are right now can be done with a GPS, and once you know that it’s first year linear algebra to figure out where you should go.

            The company that replaces programmers with computers who perform at the same level will have a tremendous competitive advantage. It sounds like a perfect startup–instead of having 5 sweaty guys working 80 hour weeks for little compensation you can have 10 computers working 160 hour weeks for free. The computers don’t smell as an added benefit.

  11. Andrea B
    Andrea B says:

    Nice cross-training work you are doing with the photography. It’s getting you to see what’s there from a different perspective, and that makes your writing even better. Which was the point that you made. Elegantly.

    • Tracy
      Tracy says:

      Oooh, didn’t even appreciate that layer of the story until I read your comment, elegant indeed.

  12. laura
    laura says:

    I have been basically dilettante for most of my life. I never needed much money and the more I did any one thing the less I liked it. I am recently beginning to feel the opposite, that being a beginner is boring. I don’t know how I will end up, because I am now 34 with a baby and barely any employment history. I still don’t know if I can be fulfilled by any one thing, but now I have a family and no money so I figure this is the time to quit putting off making a serious try at professional jobs. I can see why many people never even get this far. I am full of self doubt and frustration. I keep telling myself there is a point to it all, but on a bad day I feel like I’m fooling myself thinking that I am not wasting my time trying to reach beyond the next easy or obvious thing.

    • Penelope Trunk
      Penelope Trunk says:

      Laura, I really like how succinctly you said this: Being a beginner is boring.

      I think people all feel that way, so when it comes time to do an entry level job, they hate everything. It’s so hard for us to see that hating entry level jobs is often the path to endless entry level jobs. But dealing with entry level jobs once, efficiently, is a way to stop being a beginner.

      Just like dating, really. Getting a great date once is a way to stop going on first dates. If you can commit. If you can be brave enough to recognize that it’s time to stop being a beginner.

      We all hate being beginners. But so often we get stuck in a rut of saying “I hate this beginning stuff” and stopping. If you stop there you are doomed to stay there.


      • Marcy Brown
        Marcy Brown says:

        Being a beginner is boring. But to some of us, so is being an expert. There is a delicious sweet spot right before expertise, when there is still room for growth, that calls most loudly to me and many others. I love Dory Hollander’s _The Doom Loop System_ for outlining this concept so well.

  13. layla bb solms
    layla bb solms says:

    i found your blog a few days ago
    you speak my language
    i want to print all your posts, though to read them on paper, but i suppose that would cost a lot of cash.
    i’ve not been diagnosed with anything other than depression (16 yrs. ago) now anxiety, so who knows, but the way you write and explain life and ideas and your directness means a great deal to me. thank you.

  14. ruo
    ruo says:

    So interesting! Makes sense that cross-trained people are that much more successful! i.e. Natalie Portman with an Oscar and Harvard degree. And it’s not that hard for a dilettante to look like cross-training. For a lot of people, doing random projects is the easy part, assemblying it into a coherent storyline is hard. But for me, it’s the opposite issue.
    Thx P, changes the way I look at myself to motivate my butt.

  15. jestjack
    jestjack says:

    Couple of things…First thanks for another interesting article. Second big fan of black and white film…DW took some 35mm with her 30 year old Canon at the beach years back and sent the picks to family and friend. Rec’d “rave” reviews and have seen many of these pictures framed in familys’ homes. They thought they were “done by a pro”. Aaaand the piano for the son? I think you’ll look back and view this as one of your best decisions. Childhood memories of electronic devices will be nice – but memories of that Steinway will be – “priceless”….

    • Penelope Trunk
      Penelope Trunk says:

      Thanks for the vote of confidence on the Steinway. You should work for them :)


  16. Chelsea_Gerrard
    Chelsea_Gerrard says:

    Absolutely, Cross-training has a sort of greatness and I believe in the concept. I think learning it is like an endless journey of never ending fun. It is like being resourceful! And above all, trust me, your blog looks fantastic with monochromatic hues ;)

  17. AP
    AP says:

    I was a dilettante for a number of years, but I don’t think they were wasted years. There’s a book called “Quitting” and if anyone knows how to quit, I do. When I knew something wasn’t going to work out, I’d quit and move on. I got SO much flack (sp?) for that and was called a wanderer, people said I’d always be broke, etc. Lots of people said I should just get a job. But I like working for myself and I kept telling myself that it took Colonel Sanders many unsuccessful businesses before he found what worked for him. So, I persevered and ignored everybody (another great book), and eventually, I found what works for me. And now I’m in The Dip. Which sucks, but I’m working through it. I’m now reading Essentialism (by Greg McKeown), which is helping to get me through the dip. It’s a great book so far. I think the reason I’m in the dip is because i started doing too much cross-training and slipped into dilettante territory. I lost sight of the goal. I think if you’re going to cross-train you really have to plan it out and make sure it’s targeted cross-training (like your son with the piano).

  18. Tara Sayers Dillard
    Tara Sayers Dillard says:

    Came out with engineering degree, Jimmy Carter president & 21% interest rates.

    Zero jobs. Many new engineers waited tables. Me? Selling plants. Liked it, got a degree in horticulture, working full time, paying cash as I went.

    30 years now. National awards for garden writing, garden design. State awards for lecturing, and designs too.

    When 2008 hit I acquired licensed homebuilder/general contractor. Now my team does house renovations in addition to landscapes. Making more money than before 2008. Have not entered magazine contest yet for any of the home renovation work, you know I must win awards for that too !

    Discovered, by accident, my garden on the cover of national magazine, This Old House, this year. Digging deeper discovered the same garden was the most pinned Pin for a different national magazine, Southern Living. Had my own tv show on cbs, guest spots on hgtv, co- hosted tv show on pbs. Credibility, no money. Not a direction I’ve sought for years nor expect to again.

    Cross-Trainer? Fine, but a small definition. What I do for Garden Design is the creation of agriculture & ornamental horticulture intersecting with interior design & landscape design.

    Proof for Oscar Wilde’s, “To define is to limit.”

    I Tara’ize & have total Tara’tude. Known this since age 3.

    Created my job, filled it with everything in my DNA, pixie dust too. This isn’t ‘work’ it is my life.

    Kids? Total infertility. Did you notice before this sentence? You should have. I notice it about women before I’m told/discover.

    Most of my success, in a male dominated industry, is due to having NO kids. Able to do odd hours, and travels across Europe for decades studying the best of the world’s historic landscapes.

    Garden & Be Well, XO Tara

  19. Ariane
    Ariane says:

    I love this. I wish you’d write more about fear of career commitment.

    I’m 40, and I’ve worked a different job nearly every year of my adult life. I have several degrees and impressive job titles under my belt, and while I can certainly support myself I’ve taken some huge financial hits by living this way. I don’t know how to describe it, but after one year I always panic and quit. I’m a problem solver, organizer, and have little patience with inefficiency (INFJ). So once I’ve solved all the problems a job allows me to I get very restless, frustrated, and bored, and start looking for a new challenge…

    • Kathy Donchak
      Kathy Donchak says:


      As an ENFJ (45) I understand completely with how you get restless and that is actually a strength. I work only on the strategic parts of projects and move out of the role as things get to the last 25% of the project or sooner. I enjoy writing as my topic and focus is always shifting. Penelope’s Quistic course on MB Personality Type dives into why this happens with our type regardless of if you are an E or I.

      • Ariane
        Ariane says:

        Thanks, I will look into her courses. I’m pretty new to this site, but I’ve been doing some catch up reading. I’m also amazed by how much clearly i see things now that I know my MBTI.

  20. Holly
    Holly says:

    After reading your post and reflecting on my past I think I was lucky. I just naturally had many interests and tried to pursue them, but I also became a heat seeking missile to get my Ph.D. in psychology. Thanks for your thoughts and the beautiful photos.

  21. Heather
    Heather says:

    Great post. I’ve moved jobs after a few years a few times. Some of them have been leaps of faith that it was something I could be good at because it interested me, offered me something I could learn, but I also brought a lot of expertise to the table from past experiences. My latest job is a leap of faith that I can be good at it, but I know I have quite a bit to learn with this one. I love the challenge and the motivation I get from something new, but thankfully, I can still string it together with my other experiences.

  22. Dave
    Dave says:

    What if you are an expert dilettante? I guess it means I’m in the wrong field or at the wrong level because I generally find it interesting to learn new technologies, but it baffles me how people can spend 5 or 10 years on this stuff. I’m 47 and most jobs I get now are a high-level variation on how I did temp jobs in college, BSing my way in by saying I knew the “technology” they needed. I don’t BS anymore, but again and again, I pick up another skill and then am shocked to learn that there are people for whom this is their career and they list it as a certification, etc. But these are not useful skills for my career because there is no way I would want a job doing nothing but that.

    It’s a cop-out to call this cross-training, but maybe if I could figure out what the specialty is where the ability to pick up whatever tool is needed and master it for the task at hand is…then I would know how to move myself into the next level.

  23. JJ
    JJ says:

    I’m curious about what you think about having diversified revenue streams. We know that the key to mitigating risk in our investment portfolios is diversification – putting our eggs in many baskets, so we’re not up a creek if one of those investments turns bad.

    We probably all know people who focused their careers in one field/specialty and then things change, and demand for that specialty is gone.

    Although I see how investing in multiple career paths/income streams can be viewed as flaky, I can’t help but think having another way to make a buck if Job A falls through isn’t always a bad thing.

    Is there a way to strike a balance between flaky and diversified?

  24. Film Motoru
    Film Motoru says:

    It’s a cop-out to call this cross-training, but maybe if I could figure out what the specialty is where the ability to pick up whatever tool is needed and master it for the task at hand is…then I would know how to move myself into the next level.

  25. Adrianne
    Adrianne says:

    I really like this post. It touches on the reality that it is important to understand where your tactical (“hard”?) skills fit in with the big picture of your career arc. I ask myself variations of the “dilettante vs. cross-training” question on a regular basis.

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