How to measure your own progress

I have big goals for myself, but I try to measure my progress day by day instead of looking at the big picture. The big picture is overwhelming. For example, for the last three years, I’ve known I wanted to launch another company, but I didn’t have an idea. Or I had an idea that couldn’t grow big enough. Or I had a great idea but the investors wanted me to relocate. There was always a problem.

This is a picture of where I sulk when I feel overwhelmed. (It’s actually also the music room, and I get so frustrated forcing my kids to practice, that the room is already sort of a torture chamber, so I figure why fill another room with sulking karma when I have already ruined this one?)

But on good days, I measure my progress with three questions:

1. Am I attempting some sort of new way to make money? (You are never going to have a new way to make money if you don’t try a new way to make money and actually DO it.)

2. Am I paying back Matthew? (Every time I had a failed attempt at making money, I borrowed money from the farm bank account.)

3. Am I forcing myself to look for something that will scale? (I’m most comfortable leading a team and you can’t lead a team if you don’t need a team.)

Those questions drove me to lots of experiments with video.

I spent a year flying back and forth to New York making videos about career advice for people who said they were geniuses at developing YouTube channels. For the record, almost no one is a genius at this. Even Machinima has a roster of YouTubers with millions of subscribers (SkyDoes Minecraft has 5 million subscribers!) and they still had to do layoffs because they can’t make money from YouTube.

But I’m glad I tried a lot of video stuff because it feels better to try stuff that ends up being stupid than not trying anything at all. Feeling stupid is a good indicator of progress if your goal is to learn.

I learned that people who say they know how to make money on YouTube are mostly shysters. And I learned that I can do 20 three-minute career advice videos in two hours. I only stopped for water and lipstick.

Those videos were mostly lame. And I threw them all out. Except this one.


Hey, did you like that video? Because I’ve done a bazillion videos that are similar to that over at my company Some of the ones that feel really similar to this one:

Fast Track Your Career with Myers Briggs
Make Your 20s Count
How to Write about Your Life

46 replies
  1. Annabel Candy, Get In the Hot Spot
    Annabel Candy, Get In the Hot Spot says:

    Hi Penelope,

    Love the video even though watching it with my kids wasn’t such a good choice and your lipstick looks great!

    I run from conflict so I’ve been working by myself for 15 years because that’s a good way to avoid fights with colleagues. But I’m also about to start working on a start up with another woman which I am really excited about.

    And I think I am ready for conflict whenever it may come because differences of opinion are just that. Not the end of the world and not a personal slur. I will be remembering that in all I do with my new partner and hope that we can still get on even when we don’t get on, and still go on working together even though there are times when we may not get on.

    I’d still like to see the rest of the videos, although the funny thing is I don’t think you need this video guy to help you make them at all. He didn’t seem to do anything much apart from annoy you…

  2. Amanda Hite
    Amanda Hite says:

    So I’m on the rooftop of my building trying to get some vitamin D that doesn’t come out of a dropper and I press play on your video and my volume is so loud that a guy laying out at the other end of the roof comes over and says “well that sounds interesting what is that?” I thought well an aim of good online video is to capture attention so this has to be good if its catching attention offline…or the dude was using it as an excuse to hopelessly hit on me. Either way keep making videos you’re great at it.

  3. Greg
    Greg says:

    First: the video is good. I wasn’t sure whether your specific brand of amazing would translate to video, but it does.

    Second: all the folks with millions of YouTube subscribers say the same thing, that when they started the videos were stupid, they felt weird, blah blah blah. But they did two things: 1. they kept doing it and 2. through this, they found their unique voice. Don’t aim for perfect. Aim for evolution.

    Third: I’m not sure that looking at the aggregators or agencies is helpful, because it seems like the individual folks with YouTube channels like Tyler Oakley or Daily Grace or Jacks Gap are, in fact, making money — and scoring major sponsorship deals. The agents may not be cashing in, but it seems like the individual talent is.

    What was the process that you developed when you started your blog? I feel like it’s all the same kind of thing. Except I bet you don’t yell at your editor as much as you yell at the video guy.

  4. John
    John says:

    You should do a weekly etiquette video for the Daily Show, and this should be the first installment.

    • Lindsey
      Lindsey says:

      brilliant, John.

      Also, I think there is money to make in videos–we just haven’t gotten there yet. But, won’t everyone that is honing that skill have a leg up in 10 years?

  5. Derek Scruggs
    Derek Scruggs says:

    Re: it doesn’t matter who’s right – I’ve found that this is true of most things. Nothing really matters unless you decide it matters.

    That doesn’t mean you should go through life as a doormat. Only that deciding something trivial matters is a recipe for stress.

  6. Carmen
    Carmen says:

    This made me laugh :) It reminded me of how we were yelling at each other and arguing during our first couple coaching calls, and how that’s a fond memory, and how I’ve started taking tiny steps.

    I have so many blog posts that I can’t post. I have one titled “I Can’t Post and I Won’t Post.” I also have poetry that I can’t post because it’s stupid, but it felt good to write it….and my doodles. I doodle. The videos about doodling on YouTube are so insanely impressive. Who knew great doodling could be an aspiration.

    Great post.

    • Charlene
      Charlene says:

      Your post reminds me of how excited I am about the prospect of coaching calls being published/sold. I used to listen to Steve’s interview turned coaching session with Penelope every single day (but then it got wiped from my phone).

  7. Mairzy
    Mairzy says:

    So even though I said I would never read your posts again because you piss me off so much with your loathing of boomers (did I ASK to be born?), I read this, liked it on Facebook, and put a nice little intro in front of it. Because I’m really a Gen Y in every aspect of my life except my age. Which ought to piss you off even more. Sorry.

    • Pete
      Pete says:

      It’s not IF you asked to be born, it’s if you asked WHEN to be born. Some people were born out of their time. My mom was fond of saying that my next older brother was born 100 years too late, as he would have made a great gentleman farmer. I’m inclined to agree with her.

      • rebecca@midcenturymodernremodel
        rebecca@midcenturymodernremodel says:

        True. My son should have been born either in the age of great sea exploration (e.g. Columbus or Vikings)… or alternatively, the great push West in the United States. All his skills involve being outdoors, unafraid, learning, discovering, and survival. Very little of his skills involve math or tedious administrative tasks. That is what mothers are for. I keep telling him… “you, my friend, need to marry well.”

  8. Dannielle
    Dannielle says:

    Hi Penelope,

    There is a saleable concept here. I would say to start with a career advice TV show and then you want to be like a late-night talk show guest who throws out snippets. Sort of like Patti Stanger, The Millionaire Matchmaker.

    Regarding scale – you do not strike me as someone who should be leading a team but rather as someone who should be the center of a team that manages you.

    Also – need a more Upper East Side look. Check out the cover of Kate White’s book “I Shouldn’t Be Telling You This.”

    It’s just a matter of time – I think you will end up a quirky career coach megabrand – if you do, good luck!

    Dannielle Blumenthal

    • Penelope Trunk
      Penelope Trunk says:

      Thanks, Dannielle. You always give me good get-a-TV-career advice. But it always seems to beg the question: what life do I want? Who is the real me?

      I think the best career advice forces sharper answers to those questions. So, thanks.


      • Dannielle
        Dannielle says:

        Hi Penelope,

        I can’t talk about what you or anyone ought to do. Only what sells.

        To the issue of life goals – if you feel uncomfortable with an idea, then something about it does not match where you see yourself. Maybe a TV show would kill the family stability you want and need so dearly.

        On the issue of who are you really? I am not sure you (the subject) can answer that. Generally other people can see you much more clearly, because they don’t have a stake in what is going on.

        Not sure if you ever saw this, but I once did a short video for Brazen Careerist on personal branding. Basically it was the idea of – do what you inherently “are,” and what you will get paid for.

        At the time I didn’t realize the overlap with Jim Collins’ view:

        1) Do what you’re the best in the world at
        2) Do what you love
        3) Do what the market will pay you for

        Hopefully in the intersection of those three things, is your future. I know for me personally, it’s very hard to put into words, but I kind of “know when I’m there.”

        And please don’t ask me why I am not an actual brand consultant. Because then I’d have to tell you – “It doesn’t fit in with my life’s goals and it’s not who I am.” :-)


  9. Melissa
    Melissa says:

    I’m a long time reader but this video is the first time I’ve heard you speak… And I was so surprised! Your accent sounds so midwest. I don’t know where you’re from originally, but when I read your posts I def hear your voice accent free or maybe with twinge of mild manhattan.

    • Penelope Trunk
      Penelope Trunk says:

      That’s funny about the accent because in the midwest, people think I have a New York accent. But in NY, no one is ever fooled – they hear it as midwest right away.


  10. Senait
    Senait says:

    You should do more videos – you’re a great storyteller! Which makes you very *charismatic* ;-)

  11. Catuaba John
    Catuaba John says:

    I really like this article, someting to think how we measure our progress day by day instead of looking at the big picture.

    Hey, I like that video really funny. Great sharing

  12. Genevieve Koesling
    Genevieve Koesling says:

    Great reminder for all of us: Thank you!
    It is so important to slow down and look at your day to day progress. The big picture can be overwhelming!
    The perfect reminder for me today;)

  13. Mark W.
    Mark W. says:

    A quick comment about the chandelier.

    I like it not necessarily for what it actually is but rather for the feelings and thoughts it evokes. It makes an impression and makes me think about other things differently. Also it sends out an inspirational message to go create something that would qualify it to be just enough “out of the box” to rival it. A challenge if you will.

  14. Savvy Working Gal
    Savvy Working Gal says:

    I have been reading your blog for at least five years. During that time I’ve attempted to discuss what I’ve read and tried to repeat your advice to my husband numerous times. He thinks blogs are lame and would rarely pay attention. Today while I was listening to your video I heard him laughing from another room. The next thing I know he’s standing behind me watching the video with me. Just thought you’d want to know you may have a new audience.

      • Lindsey
        Lindsey says:

        Oh yeah, my boyfriend is similar–he thinks blogs are unnecessary fluff. He overheard part of the blogging seminar and kept putting his book down to listen. Finally, on the third night he just made me share my screen.

  15. Girl who called you for a session and you said I was like you a whole ago
    Girl who called you for a session and you said I was like you a whole ago says:

    Omg I love your personality! I don’t understand the commenter that thought you have a Midwestern accent – I hear NY (and I have a family from NY so consider myself exposed to that). Anyway, everything you said here was not only on target but interesting. Did you rehearse or does this just come out? Do you write like you talk – that flowing-ly

  16. Girl who called you for a session and you said I was like you a whole ago
    Girl who called you for a session and you said I was like you a whole ago says:

    Argh! I went to press enter and it posted before I added punctuation & completed sentence. Anyway, thx for posting.

  17. Girl who called you for a session and you said I was like you a whole ago
    Girl who called you for a session and you said I was like you a whole ago says:

    pps. This is why no one comments from their phone – a billion typos!

  18. Marguerite
    Marguerite says:

    Oh My God! I was so shocked but I LOVE IT!!!! And, believe it or not, in addition to being entertaining, it was very helpful. I have a new boss who has no clue about the program I have been running for at least 5 years. She really pisses me off sometimes and I do argue with her because she is NOT right but, you are. It doesn’t matter who is right (even though I know it’s me). She is my boss, she has a difficult job (especially with me) so I need to be less irritated and more patient. I am going to try your way. We’ll see how it goes. Thanks

  19. sarah
    sarah says:

    You tube….To make money on You Tube, you need a new idea because I don’t think there are very many people making decent money by the ads. They are dumb, and not relevant to me. To be successful is to create your own channel people want to subscribe to, and pay for. I don’t understand why people don’t charge for channels yet, because I would totally pay some of the people I follow for them to do the work finding the channels I like. I would be ok paying anywhere from $10 – $20 per year.

    It would be ideal to figure out how to market to people to make them want to pay for your channel. One, would be to throw out small “fishing” videos, for people to want. Another would be to pay You Tube to feature your channel at the end of a video. I would think this would be a market for a job, to hire a person to offer advertising packages for your You Tube Channel.

    If I had the time, I would test this idea on you, or Mr. Money Mustaches Blog. For you, I would create a personal episode, of before someone you coach, during the session, your comments after on why you said that, their feelings after, and then a couple of months later to see how they are doing. To start I would use a web cam – or a starving Camera Man who works for free in New York hoping to someday be paid, and put my money into an editor.

    I would do the same idea with Mr. Money Mustache – meeting the mismanaged money people, Mr. Money councling them, and then a follow up. If you like that idea, you should follow up with him on who he is to see if you want to use him.

    My goal would be to find enough Big Time Bloggers, to start featuring different Blog episodes, and sell by the channel or episode. If each Blogger had “X” number of followers, probably 1/3 would be willing to pay, $2.99. One camera team, One editorial team, and someone to keep the idea going….

    I would try this myself, except I am a homeschooling mom to 4 kids, and I don’t have the time, I don’t have access to the investment capital, and I don’t have the ability to find the cheap camera guys.

    Good Luck.

  20. me
    me says:

    HA ! I couldnt stand watching Seinfeld (the characters annoyed the snot of of me), but I’d TOTALLY watch a show starring you, giving advice about the intersection between work & life.

    Or, I’d even settle for watching you starring in YouTube vids like this one. I’ll definitely replay often, seeing how I cant seem to resist picking fights with my lame coworkers ….

    Thanks, P !

  21. Teri
    Teri says:

    I love this so much because I think that the whole video really replicates the style of your seminars – it’s both entertaining and educational – like the best vlogs.

    You actually should use it as a “seminar trailer” of sorts. I’ve sat through a full hour of that every week for a month and enjoyed the hell out of it, even though I totally stopped blogging 2 weeks in (turns out my medium WAS vlogs, not blogs).

    Anyways, loved the video, Penelope. :)

  22. Gary
    Gary says:

    Your makeup sucks. Or the lighting is washing your face out. You look puffy and shiny on the video. Maybe the way you normally roll, idk. Just not what I’m used to. Echo-ey, bright sound; piss poor production. Even if it is YouTube, your videos should appear more professional than that. Your post is top-notch, as usual. I thought of a new way to make money; after 21 more months of college, I’m going to get started. I quit my job for this. I need a way to make money NOW. I have applied at many places, talked with biggish wheels. I may have to become a man whore. Wifey won’t care if I bring home lots of moolah. If The Man nabs me, I’ll tell him Penelope Trunk gave me the idea. The judge will throw it out. I’m going to hush, I’m about to sound as crazy as you! Love you, GS

  23. Alexis
    Alexis says:

    Hey Penelope, what happens when it does matter who’s right? For example, if you’re a physician working in a hospital arguing about optimal patient care. That is a situation where “who’s right” could determine the outcome of a person’s health.


  24. Terry
    Terry says:

    If you have to bug your kids to practice then no matter how talented they are you are probably over-emphasizing the cello. Kids who become great musicians have to be bugged to stop practicing. Not meant to criticize you or your children, just an attempt to keep the right perspective.

  25. Jo Ann den Hartog
    Jo Ann den Hartog says:

    It was indeed delightful, after all these years of reading, to hear your voice. I grew up on the East Coast then moved to California. I absolutely agree that in Wisconsin they would think you sounded ‘New Yawk’ but from a New Yorker’s point of view it is indisputably Midwest. One of my first thoughts was of the man seen leaving the room (husband? video guy?) hearing you 30 seconds in mentioning a blow job thinking, “that’s our girl…” ;-)

  26. paeonia
    paeonia says:

    That video was good. The first time I watched it I was entertained and was all “yeah! except I don’t need to argue with my coworkers, I just want to yell at them for being incompetent”. The second time I watched it I realized it was a video on how to argue with coworkers you *like* and realized that situation *does* apply to me…I want to argue with my boss for hiring incompetent people but I really like my boss and he wouldn’t appreciate me bringing it up without a better solution than “fire them”.

    I feel a little less frustrated with work. Thanks, Penelope.

  27. Ann
    Ann says:

    Hey, I have been a long time reader and have never seen you on video. I have referred you to friends before, always with a label warning, but now seeing this, I would not do that. If I may have a vote, I don’t think you need to reference BJs and use the F word so much. It does not add value, and for me, party of 1, it detracts from your brand. I would like to see you engage creativity, insight and humor that comes from really digging into the language to get strong messages across without ever using those terms. Please take this in the spirit it is intended, feedback, delete the post if you want to. (And I do empathize with how painful it is to get kids to practice music. I compensate by playing piano myself so that someone enjoys the music room.)

  28. life coach UK
    life coach UK says:

    One’s progress can be measured based on different aspects. It can be physical, emotional, mental and spiritual. When he is able to do the things that he wanted to do for long, I think he’s in progress to undertake it.

  29. Laura Peterson
    Laura Peterson says:

    Okay, here is my thoughts about this post. First of all, I liked it. Your are great Penelope, and your video call to action is kinda natural and interesting. I have some points who I not agree totally but I respect and this is fine to me. I am not arguing here. I realized it was a video on how to argue with coworkers. I do not have to but I have employers who I need work with. Because that I contract a business coach who help me a lot and include help all the company to work together and better. If you have a chance take a look here. They are awesome. Thanks for your post. I will like you on facebook.

  30. Barbara Hoover
    Barbara Hoover says:

    Hi Penelope! I totally agree with #1, attempt to make a new way to make money! or don’t do it at all. Some of us don’t go risky because of insecurities, but basically if we don’t try a new thing we cannot gain, never. Useful Post!

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