How to find the right job for you

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We reorganized the company today. We brought in a new, interim CEO, who's not me. For many entrepreneurs, that is their worst nightmare.

But I couldn't be happier. For one thing, it's a sign that my company, Brazen Careerist, is doing well. Remember when the company was running out of money and my electricity was getting turned off? There was no one worrying then that I was the wrong person for the CEO position. No one cared because it looked like we were going under.

But then the media started talking about how we could be LinkedIn for Gen Y and we started moving fast. I don't worry about of money anymore, and we are moving at a faster speed because we can see where we are going, how we'll make money, and how we'll grow the community.

1. Know where your strengths are.
The thing that makes me great is my writing. I have spent my whole life writing, constantly trying to figure out how to earn money writing. My favorite thing I've ever written is this blog. I adore the conversation, I adore the format, the never-ending research, and the self-referential links, because that's how my mind works: connecting random stuff together all the time trying to figure out the best path to happiness. Blogging is my dream-come-true media.

But I also love building companies. So I was in heaven for two years turning my blog brand into a social networking company.

I am great in that phase of a business–thinking, philosophizing, finding holes in markets, finding holes in ideas. I never give up. I always have another idea, and I don't mind feeling lost day after day, week after week.

2. Watch where you gravitate.
But now the company needs to run fast, to execute a model we have confidence in. I am not fast at execution—I do not keep ten thousand things in my head at one time. Here's a good example: I flew to DC to talk with investors and had about five hours to retool our presentation to incorporate a new marketing plan. I spent two of those hours writing a blog post.

And the more responsibility I had for running a large team, trying to hit many goals at once, the less work I did. Honestly, I just didn't know what to do. I was outside my core strength.

And I know this: the first sign that you are outside of your strengths is when you can't make yourself do the work you need to do.

3. Find people who complement your strengths.
To get out of germination mode and reach our launch, I needed to surround myself with people with complimentary skills. I spent two years looking for business partners before I found Ryan Healy and Ryan Paugh. The way I knew it was a good fit is that as soon as I suggested we partner, they said yes, and then had a million ideas of their own.

Then, when the company was stuck financially, I found a new board member who runs a company with $150 million in revenue. He met with me every week for six months to help me focus on cash flow.

When the company was clearly moving too fast for me to keep up as CEO, I badgered another board member to be CEO. He told me a number of reasons why that wouldn't work — he had had two huge exits and he wasn't planning to be CEO again, and another company wanted him to be CEO, and he wants to watch his kids play football. These are all good reasons that I overcame, and I got him to agree to be interim CEO.

4. Do what differentiates you.
So I'm going to be Chief Evangelist. This is a great job for me, because basically, I keep blogging, and talking to the media, and I go to SXSW with my fake tan.

Most of all, I am certain I'm right about Brazen Careerist. LinkedIn is a place to display your network, not build your network. Facebook is too personal to use as a platform for managing your professional life. The way to build your network is through conversation, and Brazen Careerist is a great tool for that network-building conversation that gets you control over your career. (And hey, you should sign up!) I can talk about this all day.

5. If you really can do the job, you'll be doing it already.
Recently, I did a live chat on the Washington Post web site, answering fifty questions in sixty minutes about how to use social media to help your career.

The chat was fun, and people asked interesting questions. It was great exposure for Brazen Careerist. But during that hour I couldn't help wondering: Who is making sure we're hitting marketing numbers? Who is going to hire the new head of sales?

Now I have an answer: Ryan Healy.

In any office, employees gravitate to the job each should be doing, no matter what the titles are. Sometimes we gravitate to a job and it's not available, and we go nuts doing something we shouldn't be doing. Sometimes we gravitate to that job and it's such a good fit for us that we do it even without a title.

Ryan Healy has been running day-to-day operations of the company for a while now. Without the official authority. Because he's great at it. While I am thinking of ideas and philosophizing, Ryan is always asking, “What are we getting done?”

A lot of people say they should be doing a job they do not have the authority to do. Here's some news, though: You'd be doing it already if you were great at it. Ryan Healy is now Chief Operating Officer at Brazen Careerist because he's already shown he can do the job. That's how you get serious promotions: doing the job first, in an outstanding way.

Okay. So what you can expect from me is more blog posts, because when my blog traffic goes up, it's good for Brazen Careerist. And you can also expect to see less of me feeling frazzled and crazy and fighting with Ryan. Because I'm not anymore. I'm back in my sweet spot, and I feel so lucky to be here.

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  1. Kara
    Kara says:

    “And I know this: the first sign that you are outside of your strengths is when you can't make yourself do the work you need to do.”

    I love that line Penelope. It really put some things in perspective for me. Thanks.

  2. Alex
    Alex says:

    Great post. I’m thinking about my career a lot these days and I find your blog incredibly helpful in steering my thinking.

    Also: let’s see pictures of this fake tan.

    • Penelope Trunk
      Penelope Trunk says:

      Yes! You should still join! The network is for people who understand that we are each responsible for our own career path, and we can get more control over our lives if we build our own network. This is not about when you were born, really. It’s about what your mindset is.

      I think anyone who reads my blog would fit in at!


  3. Scott Annan
    Scott Annan says:

    Great post Penelope – it’s true that once you find the right path and are doing something that you are passionate about (and that people want!) you grow momentum quickly!

    One more thing to note is the importance of your network and ability to grow it, while keeping those initial customers loyal, connected, and big fans of your business.

    We use Network Hippo ( to stay in contact with our customers, grow our network, and reach out to new people.

    I think that networks should be the 6th point in your list – otherwise, awesome post – thanks!

  4. Christine Livingston
    Christine Livingston says:

    I’m inspired by the organic way your business appears to have grown and how people have migrated into roles that are good fits for them and which they have ideas and passion about. There’s got to be a lesson in this for other businesses, even bigger ones, about sometimes listening and watching what’s happening naturally, rather than having to force fit things, don’t you think?

  5. Mark W.
    Mark W. says:

    Congratulations on your new position as Chief Evangelist at BC. Definitely a good fit for you.
    I really liked this thought – “A lot of people SAY they should be doing a job they do not have the authority to do. Here's some news, though: You'd be DOING it already if you were great at it.” So true.
    I always look forward to the new ideas and platforms being launched over at BC.

  6. fd
    fd says:

    thanks Penelope for this in particular:
    “And I know this: the first sign that you are outside of your strengths is when you can't make yourself do the work you need to do.”
    this is where i’ve been stuck for months. and i am trying to do my jobs anyway and do them better so that i am in a position to meet the right people and manoeuvre my way into something more suitable but its exhausting and so far just bringing me back to square one.
    somehow its encouraging to see my instincts about current job position so clearly written in black and white.

  7. Adam
    Adam says:

    Hi Penelope,

    Loved this article. You’ve mentioned a lot of things that I’ve known intrinsicly for a while, and paid lip service to, but have only really consciously started to act on in the past few weeks.

    Like you, I’m a great idea generator. I get on a roll, and suddenly I’ve created 3 major projects, all of which I’m managing.

    Now, this is where it gets difficult, like you said above. My core strengths are in idea generation, the linking of concepts, and communicating visions for the future. However, I’ve sometimes found it challenging to take these ideas and get them up and running.

    I’m working now to try to leverage my colleagues and play to their strengths as well. Time will tell how successful it is, but even if it isn’t a 100% success on this project, I’ve learned some key lessons from this that will allow me to plan better in the future for these types of challenges.

    Thanks for stating everything so clearly!

  8. Sydney Owen
    Sydney Owen says:

    I also have to add a major point: find a mentor. The best part of watching you succeed is being a part of this community, and being someone that you have invested your time in. I love seeing your successes and those of the Ryans as well. I am thankful for the opportunities I’ve had that have sprouted from your advice and guidance and every day I’m thankful for having met you and for having the balls to ask you to jump in this journey with me.

    Something else I’d like to add, something you’ve been telling me since day one of our mentoring relationship – be a star performer. Everyone wants to be part of someone’s success. You can know if someone is a star performer within 30 seconds of meeting them. I’ve been channeling my inner PT as I guide two PR students through the same process you helped me with.

    I’d advise everyone to seek your advice, but then you’d be inundated with even more questions than you already have on your plate as it is.

    Keep it up. Your strength through this entire process, at least what I’ve seen of it, continues to make me beam with joy, as if I had some role in it.

    Congratulations on your new role, how incredibly appropriate the title.

    See you in March (unless you’re in Chicago before then, and if that’s the case, you need to call me…)

  9. Kevin
    Kevin says:

    I think age has little to do with joining a career/networking site; I’m over 40 myself, but wanted to learn more about using online social networking, as I’ve never been much of a “talker”. I do, however, want to try and improve my presence both personally and in online world. I really understood this post as I’ve seen it firsthand in most of the places I’ve worked – just never really thought about it in this way. Thanks Penelope!

  10. bill
    bill says:


    As a long-time subscriber of your blog and occasional critic of your writing, this is easily my favorite post because I think you finally find the right ‘niche’ for yourself in your own organization. :-)

    You’re an excellent writer, so you should keep doing it, and doing more of it. I still believe that the key of your business is your blog and your brand, not the social networking/”linkedin for generation Y” crap, but I’ll leave time to prove I’m right or wrong. I think your brand (which is your core asset) will get stronger as you spend more time writing.

    Look forward to more thought-provoking and entertaining posts. :-)

  11. J
    J says:

    I’m very happy for you Penelope!

    And thank you for that insight about naturally gravitating towards the roles you should be doing- I believe that and it’s given me a lot to think about/evaluate as I consider my next career move.

  12. Jim
    Jim says:

    This is all very solid advice, Penelope. Doing what differentiates you is especially important, considering the increasing avalanche of new ideas, products, services, blogs, etc. in cyberspace. For me, this point is very important because of the career transition I’m starting. Thanks for sharing…J

  13. econobiker
    econobiker says:

    “A lot of people say they should be doing a job they do not have the authority to do. Here's some news, though: You'd be doing it already if you were great at it.”

    Or you’d be doing it already if you were good enough at convincing a few key people that you are great at the jobeven if you are actually not even competent and lean to the side of backstabbing and stomping on underlings methodology of workplace politics…

    It isn’t all “ra-ra”- “cheer-cheer” in the real world… as opposed to in blogger-tisements like this one …

  14. prklypr
    prklypr says:

    Another great post, Penelope. Your happiness makes for much better posts, so stay happy! I do have to quibble at bit with the title – this post is not so much about how to find the right job, but how to find the place within an organization where your skills really shine. Kudos to you for recognizing that you could not do what needed to be done, then figuring out (a) who could do it better and (b) what you should be doing instead. And more time for blog posts is a bonus for us!

  15. Marilyn
    Marilyn says:

    Thank you for using the phrase “outside your strengths” rather than “outside your comfort zone”. I cannot handle hearing about any more comfort zones!

    Congrats on your new freedoms in your business!

  16. Carly
    Carly says:

    This post really helped put my perspective in order. I am an entrepreneur in the midst of re-organizing my business and priorities, and this point in particular was exactly what I needed to read: “the first sign that you are outside of your strengths is when you can't make yourself do the work you need to do.”

    Congratulations on your new position! I joined BC today.

  17. Beth
    Beth says:

    This was a post I needed to read – I have been doing jobs that I hate and procrastinate at for years – but needed the “paycheck.” I need to find what I am good at and go. BTW, I too have been reluctant to join your site as I too am over the dreaded 40. I am joining today…

  18. Dennis
    Dennis says:

    You may (not) be surprised by how many entrepreneurs find themselves in that position.
    But the other story in your story is how, only when the business model ‘clicks’ doe severything work.
    We run a fairly straightforward business, but it took about 3 years for the idea to click. I advocate to my clients about the importance of getting the ‘proposition’ right.
    Looking in form the outside, it seems to me that ‘LinkedIn for GenY’ was that aha moment. I had mine recently too – and even posted a screencast explaining our model to myself and to the world.

    And Like you, I prefer writing to the running the company, but unlike you I don’t actually do the writing but just bitch about not getting to it.

  19. melanie gao
    melanie gao says:

    “My favorite thing I've ever written is this blog.”

    My favorite thing I’ve ever read is this blog. Seriously, every word for the last four years. Every word in the posts, every word in the comments. You have given me so much to think about, so much to talk about.

    Congratulations on your new position!

  20. Linda
    Linda says:

    I love your posts. I also liked how you mentioned that LinkedIn is a place to display your network and not build it. I’m a graduate student and my internship and university was pushing us to build our networks through LinkedIn.

    The students didn’t agree with it but we didn’t have a way of explaining why. We just knew that wasn’t how we were going to build ours.

  21. Kriti
    Kriti says:

    Penelope. Wow.

    Short question: What do you think of career counselors, and how do you 1) figure out your strengths and 2) align them with matching jobs (I don’t need a job that matches me perfectly, but just doesn’t do something detrimental to humanity, or make me cry TOO often).

    Long version: You hit so many nails on the head. Me? I love creativity, writing, problem-solving, thinking of concepts, public speaking, art, talking to people, multitasking, great at learning new languages and travel, and generally being on fire. I can talk about ANY topic that makes 99% of people feel uncomfortable, but few topics that people consider light-hearted day-to-day conversation. I’d make a fabulous “communications person”… or a shrink.

    I’m small, female, cute, and incredibly approachable, so that all works well in these types of roles (except that I’m an introvert and want everyone to go away at the end of the day).

    But then I think: where is the scope and glory in that? I got lucky in that I got really, really educated – and have loved it – shouldn’t I be putting that to the best use possible?

    In other words: I am confused. Please comment, Penelope, or other readers :)

    A happy, new reader,


      • Kriti
        Kriti says:

        As a college professor? Partly!

        I think it would be fun, promoting your work / grant applications / teaching / lots of research initially… and I have randomly ended up with a good foundation to start (connections, types of schools).

        Always had a slight bias that it’s “ivory tower”, but now in school for the second time (in a place I love) that perception is changing…

        Should I pick my advisor’s brain about what her life is really like, on a day to day basis, and what it took her to get there (successful public health professional whose research is literally saving lives)?

  22. JP
    JP says:

    1. Is the purpose of this post to position your company in the next phase past “barely in business startup”? You are open about your sex life, why not tell us about adoption rates for your app.

    2. Why is your new CEO’s name a secret? Doesn’t seem like your culture.

    3. Get some metrics to measure your success with this new abstract job/title. The idea is that you need to stay humble and attached.

  23. MC
    MC says:

    Hey Penelope,

    Great to hear things are on a roll. I was kinda concerned though. Didnt your last twitter post say you were having a miscarriage!!?

    Hope you are ok woman!!

  24. Lauren Flanagan
    Lauren Flanagan says:

    Great post, Penelope and as a small investor, glad to hear about Brazen Careerist’s progress.

    Chief Evangelist is a huge job. You’re probably too young to have experienced it, but Guy Kawasaki’s evangelism was one of the big game changers for Apple. He coerced, cajoled and courted developers like me by the legions to write cool sw for Apple computers and a revolution was born. Don’t underestimate your power to persuade and influence, especially when you’re doing what you love to do.

    Look forward to your “Lessons Learned” contribution at the EQUITY MATTER, THE ROAD TO NASDAQ Seminar next week in at the Fluno Center in Madison. Please do tell all!


  25. Jennifer Ellis
    Jennifer Ellis says:


    This post is so timely for me as I begin recruitment for the two staff positions that report to me. What I’ve learned during my time with the staff I inherited is that their strengths do not complement mine and that is a problem. I need confident careful execution people who can own my program in my absence – freeing me up so I can have the big ideas and build the relationships.

    Also, I completely agree with your point about gravitating to what you are good at, even if it is out
    of your scope. I frequently volunteer (and get volunentold) for the projects that are appropriate for director-level management because they suit my skill set, regardless of my title.

    Thanks for this post. Well done!

  26. calisara
    calisara says:


    I just recently joined Brazen Careerists, it takes some time to navigate and fully comprehend, just like any other social media site/blog. Loved your comment on facebook, because I try to get that across to every single business owner. That having a fan page and a business does not equal social media success, but they keep on trying to acquire “fans” who are really people that are just too nice to NOT fan them. Not actual fans. I do fan a few people, 4 to be exact. And these are people I have gotten to know more than just a blog, and who I actually am a fan of… maybe one day everyone else will learn. I’ll keep dreaming.

    Good luck and yes, good night.

  27. JPeep
    JPeep says:

    “And I know this: the first sign that you are outside of your strengths is when you can't make yourself do the work you need to do.”

    So, so true. I’m in the final stages of post-production on a film, and I am SO NOT THE PERSON to be pulling the logos and the credits and all the little things that will make it finished together.

    • Ian
      Ian says:

      If you don’t do it at least once yourself, you’ll never be able to tell if the person you hire next time has done it right.

  28. Kathy Caprino
    Kathy Caprino says:

    Great stuff, Penelope. Thanks! I’d like to add that there are thousands of folks today who are fabulous at things that they’re not yet doing. For instance, I went from a miserable and chronically sick corporate VP to supremely happy career and life coach, author, speaker, and small business owner. For 20 years, I hacked out various corporate roles I felt disconnected to, because I didn’t recognized and honor the other talents in me. I had an inkling, perhaps, of what I was capable of, but the professional identity I carved out for myself for years (marketing VP) didn’t allow for those talents to emerge. If anyone feels they’re meant to do something different from what they’re focused on now, but can’t figure out what, please check out my book Breakdown, Breakthrough ( for help reinventing. You’ll know you’re doing what you’re meant to and what you’re great at when you finally feel joyful, fulfilled, and aligned with your work. Thanks for all your great insights!

  29. Philip
    Philip says:

    Congratulations on your “demotion”! I’ve seen lots of businesses ruined because the “idea person” who started it wasn’t able to let go and turn it over to the “details person” it really needed to survive/thrive. Kudos for avoiding that trap! Good luck as evangelist!

  30. mm
    mm says:

    I have to agree completely that the best way to land a promotion is to be doing the job that you think you should have already. My first job out of college was as a Marketing Assistant…..8 months later the Director of Marketing quit and I was promoted to his position and in charge of running the entire department. It was an incredibly smooth transition and my General Manager didn’t seem the least bit concerned that a 23 year old who had no prior work experience would be able to handle the job. This opportunity was only afforded to me and I was able to succeed in it only because I excelled at my Assistant position and then began taking on every “Director” task that he didn’t feel like doing. The moral here is that this advice works, I have seen it first-hand…..if you really want to be doing a certain job, just do it, regardless of your official title and people will notice….

  31. Dale
    Dale says:

    Hey Penny, so what’s next? As someone who’s lived vicariously through your exploits for the last 7 or 8 years, I can’t wait to find out.

    My money is on another book, then a TV show:)

  32. Jennifer H.
    Jennifer H. says:

    Congrats on the new direction — must be a huge relief to turn over the reigns.

    I noticed that several people commented on your quote: “the first sign that you are outside of your strengths is when you can't make yourself do the work you need to do.”

    While I don’t necessarily disagree, it’s also crucial that we don’t adopt this mentality for everything. One of the main ways we grow is by making ourselves do hard things. True, sometimes we need to enlist others to complement our strengths. But I know plenty of people who shirk their duties (even the basic ones, like taking care of their children) b/c they can’t make themselves do the work they need to do. Then the “cop out” becomes merely another excuse for laziness.

    I think the key difference where you’re concerned is that at least you tried for a while to make it work and then recognized a different course would be better for everyone involved in your company (not just an excuse to make your life easier for you).

  33. Lia M
    Lia M says:

    I’ve had a trying week building my business and reading your blog helps me think that my challenges are just momentary bleeps…thank you for writing honestly.

  34. Sarah Bush
    Sarah Bush says:

    Hi Penelope!
    Great post. One thing I’d love for you to comment on is this sentence:
    “I always have another idea, and I don't mind feeling lost day after day, week after week”.

    I’m starting my own business and I always have another idea, but I have trouble “feeling lost day after day, week after week.”

    Why don’t you min?
    What do you do to soldier on through that?

    • Penelope Trunk
      Penelope Trunk says:

      It’s the hardest part about having a startup — the lost time. I am so excited to have ideas that the lost feeling feels sort of safe. Like, I’ll figure something else to get out.

      But honestly, I have been on the edge many times and it’s a hard way to live. If you are lost week after week, you are never totally sure where the edge is, and how long you have til you’re on it.

      The key, like everything else in life, is to believe in yourself and what you’re doing. (So easy to write. So hard to do.)


  35. Pat Rocchi
    Pat Rocchi says:

    Your success is illustrated at the top of your post: You do not possess so much ego that you are unwilling to hand the reins to someone who is more capable than you in that role. That is traditionally the downfall of entrepreneurs. Good for you, and the best of luck to you.

  36. Pirate Jo
    Pirate Jo says:

    “I noticed that several people commented on your quote: “the first sign that you are outside of your strengths is when you can't make yourself do the work you need to do.”

    While I don’t necessarily disagree, it’s also crucial that we don’t adopt this mentality for everything. One of the main ways we grow is by making ourselves do hard things.”

    Jennifer H., I couldn’t agree with you more on this. I just left a job where I was in exactly this same situation. I was hired to do one thing (“Business Analyst” – it involved a series of responsibilities) by a relatively new (but very good) manager, and as things turned out, the team didn’t need that. I had every justification for quitting after three months, but I rolled up my sleeves and pitched in to help out the people who I could see needed more help (“Prod Support”). I took on their crap work.

    As it turns out, I’m really not qualified to do “Prod Support.” I could plug the holes in the dam, but not fix them, because I simply don’t have the background, education, or experience. The job description requires a 4-year degree in computer science, plus five years of experience in one or more of several very technical disciplines, which is a pretty accurate assessment, and I have none of that.

    My boss and I agreed I wasn’t in a position where I could really succeed, and I had no desire to make a career out of it anyway. (I will never again take a position where I have to do 24-hour, on-call support.) So I left with a glowing manager reference, a team that’s really going to miss me (now they are stuck with the crap work again), and found another job within a week.

    It was the most stressful period in my career history – imagine spending your time stumbling around in the dark, looking for a lightswitch. I was in WAY over my head, which was really hard for me, because I care about excelling at what I do. But I have no regrets. I got the chance to learn something completely new and different, and I don’t even know yet how that will come back to benefit me. I worked with the best team of people I have ever worked with, and even made some friends I will continue to see outside of my work life, in a purely social setting. I also paid $33K toward my mortgage.

    Yet, I am also glad it’s done. A year and a half was enough.

  37. Robyn Barsky
    Robyn Barsky says:

    Penelope – I do career counseling and this is so right on. It is a point that many, many professionals miss and I hope you find a way to syndicate this piece as far and wide as possible.

  38. Rick Smith
    Rick Smith says:

    I agree 100% with this post:

    1) I was a founder CEO who grew a business (world 50) to nearly an 8 figure run-rate, but the business had moved past creation and initial sales (my strength) to consistent, efficient execution of the model (my weakness). I brought in a new CEO with those strengths and the business has thrived

    2) I just published a book about this very topic, The Leap (released last thursday). Accompanying the book, I have provided a free, unique resource to help people quickly find the intersection of their strengths and passions ( This seems to be a strong area of interest – site has had nearly 200,000 pageviews in just the last 3 months! I am a “Purple Heart”, my wife is an “Electric Lime”

    Great move, Penelope. Getting beyond the ego part of it allows you to thrive!

    Rick Smith

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