How to get the guts to go freelance

It’s another post about Melissa. But before I get any more emails asking if Melissa is single, let me just say that the single life of Melissa lasted exactly three days.

I could see it coming, really. She said, as she was trying to figure out if she should break off her engagement, “I always think I should just go move in with his best friend.”

Okay. So fine. It is not normal to have these thoughts so close to the wedding. So she moved out. And then, just as she was gearing up to tell the best friend that she wants to be more than friends, he volunteered to help her move her stuff into a new apartment.

I’m skipping the part of the story where they make out on the sofa and I’m going to straight to the official blog photo of him.

You will notice that he has set boundaries with me via Melissa, so I am not putting his picture on the blog. It’s probably better. Because the last two guys Melissa dated had their pictures on the blog, and then look what happened. Badness. For both.

So we are breaking the cycle. Instead of showing you his face, I will show you his Myers Briggs score: ISTJ. This is a good match for Melissa because he is loyal. Also, he seems to have infinite patience for Melissa.

Not many people have this patience. For a while Melissa has been pretending to be employable. But now I can tell you: everyone has fired Melissa. Including me. I fired her and got so pissed off at her that I sent her to go live at someone else’s house for three days and that person was not even, really, my friend. But look, we live out in the middle of nowhere. There are not a lot of choices.

But to be honest, I have been fired from every job I’ve ever had, too. People who get fired a lot get really good at quitting before they are fired. And also they get good at staying for a while and not working while they watch the company gear up to fire them. Managing how you are getting fired is an art form.

You can tell if you should be working for yourself by how many times you’ve been fired. When you are counting firings, consider the time when everyone hated you but you were so difficult to confront that they let you coast until you found something else to do. That counts.

The way you tell if you should work for yourself is that you are unemployable. Because look: it’s really hard to manage cash flow on your own, and it’s really cushy to have someone hand you a paycheck every two weeks. So of course, if you can manage to behave yourself at a job to have a steady paycheck, you should do that.

Melissa is not one of those people. To explain why, I have to explain that Melissa’s idea of fulfillment is sitting on the sofa, reading the New Yorker, and then other reading that’s within reach of the the far corner, which is the spot in every sofa in any room that she will choose to sit. She requires that every three hours there is someone to hear her output. That is, she has synthesized the information and determined what is important for people to know, and she needs them to respond to her. She needs someone to say, “Yeah, that’s a good one.”

Here’s what that looks like:

This is from a project where twentysomethings posed with all the stuff they own. Melissa sends me a few samples of photos and she reminds me that she also sent me, I don’t know, like ten weeks ago—she has a photographic memory—an article about how Gen Y doesn’t buy stuff. “It all goes together,” she tells me.

She doesn’t care if I agree with her. She just wants to be heard. But I admit that I clicked the link to see all the photos of what young people own.

So Melissa goes to a job, any job. And she blows them away by how competent she is. People fall in love with her. Bosses want to marry her or set her up with their best friend’s nephew or whoever they can find because they can’t let this brilliant woman with a porn-star figure slip through their lascivious hands.

Then they work with her for a few months, and they notice that she gets ornery if they demand such high output that she cannot read online. Then, if she can last five months, they start to notice that she disappears in the middle of the day. Bosses tell themselves it’s a coffee run. But it is too long. They tell themselves it’s lunch that is just a little too late. But it’s also just a little too long. And then, it turns out, they see, once, maybe, by accident, that she has found the nearest sofa, which is surely not really near, and she is curled up in the corner, reading magazines, like she doesn’t really have a job.

And then, of course, she doesn’t anymore.

So this time when she got fired, she panicked because she didn’t know if she should put her last job on her resume.

“I only lasted six months,” she told me.

“Just leave it off,” I said. “Just make it look like I was your only job.”

I do pay Melissa for stuff. I used to not want to pay her for stuff because she gets fired from everywhere. I was scared I’d have to fire her, too. But everytime someone would mess up something of mine – a media kit, my web server, health insurance – Melissa would fix it. And she would do a better job than I ever imagined could be done. Cassie even wrote a blog post about how Melissa can swoop in at the end, when everyone is screwed, and fix stuff.

So I started hiring Melissa for random stuff, because she can do anything as long as it does not last longer than one New Yorker cycle. And now her resume could be a complete train wreck of unrelated jobs she was fired from before the year was up, but instead, she looks stable and reliable because she shows that she has been working for me for years.

So I tell her to leave off the millionth job she’s been fired from. And she starts to cry. She says she is never going to hold down a job and her life is going to be terrible and she will never have stability. And while she is not saying this, I know she is also thinking that she will never buy expensive shoes again.

Back to the boyfriend. He is very excited that she is home when he gets home. It’s fun to have a stay-at-home girlfriend. So fun that he decides she can move some clothes to his house, which I could have sworn she had already done, but you know how the moving clothes in thing is:  the girl does it furtively, til everything is there, and then they may as well get engaged.

He likes her being home all day and she likes being home all day, and then she starts looking for jobs and she sends them to me to see what I think.

“These are all part-time,” I tell her. “You will starve.”

Then we have a revelation. She can do part-time, project-based work. She loves that. And she is great at getting that kind of work. She can pitch herself to do anything that involves the computer because honestly, she can do anything.

Earlier in her career, like after every single job she’s been fired from, I suggested that she start something of her own, but she hasn’t wanted to. “I’m not a risk-taker,” is what she’d tell me. But at some point in a project-oriented person’s career, continuing to take full-time jobs is too risky. Because you’ll never succeed long-term, you always burn bridges, and you start to feel like you have no skills that can help you keep a job.

Melissa hits that point and she decides she is going to freelance. And she’s excited. Freelance work has always been what she should be doing, I think, but she couldn’t get excited about it until she saw it as the most low-risk option she has.

So she gets a job doing online marketing. She gets a job doing SEO. She gets a job taking photographs of kids, and then I realize she is not going to have enough time to do my stuff. So I tell her that she needs to be careful not not take on too much work. And I give her a raise, because when she’s doing what she’s good at, she looks much more valuable, even to me.


73 replies
  1. Jim
    Jim says:

    Don’t we all back into figuring out what works for us? We try the established patterns first and where they don’t fit, hopefully we take it as positive feedback rather than negative (I suck).

    I’ve learned about myself that, at work, I like to start and build things, but once they become operational I lose all interest. I used to think that I didn’t have what it took, but now I see that I’m just good at starting things. So I’m about to go start something else at another company that wants me to build something for them, and when it’s operational in a few years I’ll cheerfully go find something else to start.

  2. Jenn
    Jenn says:

    ISTJ will be great for her. My hubby is ISTJ. I am like a top spinning round and round and he is the walls that I bounce off of, keeping me someplace safe.

  3. Harriet May
    Harriet May says:

    I love it. I’m so happy for Melissa. And I think I should find out what Myers Brigg type the med student is, so you can tell me if we’re a good match.

  4. Paul Hassing
    Paul Hassing says:

    Beautiful writing, P. The bit about seating really resonated with me: :) I’ve run a copywriting business since 1999. For every hour of creating, there’s at least an hour of admin, drama and faffing. Now, after all these years, a talent agency has approached me to go on their books. I’m giving it a go. Now THEY will find clients, extol my talents, secure gigs, take briefs, haggle rates and chase payment. All I have to do is be amazing and enter a weekly time sheet (to get a weekly payment). It sounds like the best of both worlds. It’ll be interesting to see if it actually is. I wonder if this approach could work for Melissa … Kind regards, P. :)

  5. Meghan
    Meghan says:

    This is an exceptional helpful post for me because I’ve been wondering if freelancing is the way to go for me. But now I am more decidedly in the “no” camp, because I am highly employable and find it relatively easy to get along well enough to stay at a job.

    Though my goal is to strike the right balance between performance and output and the ability to read online and daydream in between projects.

    • Penelope Trunk
      Penelope Trunk says:

      Meghan, this is such a great way to think about work. It’s a great model for other people to use.

      A lot of people want work to be different even though they are fine at keeping a job. Getting work to be different almost never requires switching to freelance. It requires setting better limits at work or asking directly for what you need at work.

      People who can hold down a job and get a regular paycheck are, in a way, freed from the worst parts of earning a living and they therefore have more time to think and do other things.

      A steady paycheck is more freedom for most people than freelancing and self-employment are.


      • liveonfred
        liveonfred says:

        Penelope, thank you for your blog. I’ve been a regular reader for a year or so, but don’t comment often. Your insight and self-reflection have helped me to better examine myself to determine where I might best fit in this world…still a work in progress.

        “People who can hold down a job and get a regular paycheck are, in a way, freed from the worst parts of earning a living and they therefore have more time to think and do other things.”

        What you say here is so true. I’ve been trying to convince myself for a decade to appreciate my secure full-time employment and I do. At this point, I’m pretty efficient at it, leaving me plenty of time to think and do other things.

        My problem is that all of my outside-of-work thoughts are centered on searching for a better career path, developing business ideas, and scrambling during my free time to build a better life. I have started side businesses based on a few of my passions and talents, only to feel like a failure because I cannot grow and nurture them. Since I’ve been such a wimp about leaving my job, I always end up putting my plans on hold, throwing myself back into my career, and trying to stick it out. I work really hard at trying to do my job well, enroll in graduate classes to improve my skills and advancement opportunities, fake that I’m happy, and go home to enjoy my life with family and friends.

        But this can only last a few months until I crash. Anxiety sets in and I again scramble like a manic mad woman to discover what will really make me happy in my work. So…I begin planning a new business (again) or pick up on one where I left off. I become too busy for real life, but the excitement of a joyful future keeps me high, for awhile, until I have no energy left to keep up the momentum and my insecurities poison me with self-doubt.

        I don’t really have a life.

        It took a few years of therapy (since no one I know can understand this struggle, I have to pay for someone to listen), but I know I have to leave my full-time job. I’m still working on shedding the guilt I feel about quitting a good thing, but a flexible project-based career is always what I really wanted. I must at least give it a try.

  6. Kat Alexander
    Kat Alexander says:

    Great post, Penelope. Your seminar was a powerful and helped me make writing a priority. Melissa did an excellent job orchestrating and I had no idea there were past challenges!

  7. Jules
    Jules says:

    There are soooo many benefits to doing freelance and contract work. It definitely takes some guts to transition to this lifestyle and away from a steady paycheck and benefits, but it’s exponentially much more rewarding at the end of the day (I think).

    Congrats Melissa! More people should take the same career leap…

  8. Diana
    Diana says:

    Not to sound judgemental, but are you really doing her any favors by helping her deceive potential employers/clients? Because that is what it is: pure deceit. Honestly, I have been a hiring manager for 20 years and I would not let either one of you through the front doors of my building.

    But I do love your blog. :)

      • Diana
        Diana says:

        Uh..huh. And if I had said “I manage my own company (I do), I suppose you would have said she is hired by Fortune 500’s, or whatever. My point is there is no reason to lie about this on a resume. Most 21st century companies understand there are different personality types out there (the Myers-Brigggs is no secret), and we appreciate those who know and are comfortable with who they are. Without lying about it. In fact, if you thought you would have to lie because they wouldn’t understand, I don’t think you would have a good fit. If you have to lie for yourself, that’s a different story.

    • Morgan
      Morgan says:

      How is resume editing deceit? If we all listed our failures on our resume rather than our strengths and experience for the job to which we are applying, no one would get hired, ever.

  9. AP
    AP says:

    “This is a good match for Melissa because he is loyal.”

    Well, except for banging his best friend’s ex-fiancee.

      • CL
        CL says:

        Yeah, I am curious about this as well. I know that we have imperfect information, but Penelope really left us hanging there. What would cause a person with an extremely loyal nature to turn his back on his best friend and swipe his former fiance?

          • CL
            CL says:

            Saw it. You overestimate the power of a woman’s body though. Melissa has some stuff to back it up (ex: brilliance, ability to do everything, and photographic memory), but she also, as Penelope points out, can get ornery and you must be infinitely patient with Melissa. That’s why I’m curious – Melissa is superficially very attractive, but on longer acquaintance you see her quirks. This bf’s best friend turned lover saw the quirks and the breakup but still went for her. There is something missing (imperfect information).

          • CL
            CL says:

            It’s not so much crowdsourcing the superego as allowing Penelope to rewrite this story so that Melissa is not a cheater. Penelope’s story is that everyone wins: Steven gets to dodge a bullet with an incompatible chick, Melissa finds love, and the best friend gets a gorgeous, brilliant girl. Writing at its finest.

          • AP
            AP says:

            And I think the conclusion we can come to is that we should listen to Penelope about work matters where she is typically spot-on, and stop there.

          • Passingby
            Passingby says:

            That’s good writing: you see the pictures, and there is no “porn-star” body there. As for the brilliance-being a nanny while pushing 30 doesn’t sound like the brightest crayon on the box, but there you go.

  10. Becky Castle Miller
    Becky Castle Miller says:

    I’ve been freelancing for six years, since my oldest daughter was born (now I have three kids). My husband (ENJT) has had good jobs, so any money I’ve earned freelance writing/editing/marketing has been gravy. Now we’re living in Europe, and it’s REALLY expensive to live here. I’ve continue to freelance for a couple American clients, and I have some good opportunities coming up that wouldn’t pay well but would be fulfilling (I’m INFJ).

    I have an opportunity to pursue a full-time job (interview coming up next week), and I’m not sure if I should take the full time job working for someone else because the money would be very helpful, or just tighten the family purse and keep pursuing freelancing. Really, I want to be able to make enough money to hire someone to do my housework. Because I would rather sit at a desk and edit copy than stand at the sink and wash dishes.

    I’m not sure which option is “brave,” which one would require more guts in this case.

  11. Monica Leonelle
    Monica Leonelle says:

    There is nothing deceitful about this. Melissa has worked for Penelope for several years in some capacity. And you do not have to put everything on your resume. So I don’t understand what the issue is, Diana.

    Also, I don’t think it was any secret on this blog that Melissa hopped from job to job. I went through something similar to her, where I kept telling myself, “This time I HAVE to like my job.” I’d quit within 6 months, typically. Every once in awhile, I got fired. And in the last job, I wanted to quit about 3 months in but realized I could easily coast for another three to six months by being so nice and fun that no one wanted to fire me. That job felt so guilty that they kept me on their payroll for over two months afterwards under some bizarre severance package that no real company would give.

    I realized before taking the last job that I’m much better at project-based work. Once they fired me, I just started doing that. It’s not stable in a traditional sense, but it is significantly better than the emotional turmoil of committing 50+ hours of your week to a company when you know you will probably lose interest.

    Also, at the last job, I used the “be nice” tactic to prolong my firing, but in doing so made some close friends who thought I was super enthusiastic about being there. It was devastating for both them and me when I was fired, even though I knew it was coming. I realized afterwards that I had basically lied to them the entire time I was working there, and that felt terrible. It was also impossible to explain that the firing was planned and just made me look like an idiot who couldn’t accept reality.

    For some people, it really is better to freelance. I am good at marketing myself, and I can do a wide variety of tasks. Those are good traits for freelancing. It is obvious that Melissa has those too.

    I hope Melissa is happy with her choice. I also think she should consider doing some online workshops of her own, perhaps about photography, or even about trends from the New Yorker. As a blogger, I would pay for someone to read a ton of research and point me to the best stuff on a weekly basis. It is really exhausting to keep up + produce content.

    • Penelope Trunk
      Penelope Trunk says:

      Monica, thanks so much for this comment. You describe so well what it’s like to be fired and realize being fired was right.

      People always write the “what I learned from getting fired” posts (me included!) but really it’s painful and Melissa sent me one article than said people are so stressed when they’re getting fired that they temporarily lose their hearing.

      Most people who get fired are either burning up with anger or paralyzed from fear.

      The strongest people take action based on what they learn about themselves from being fired. You tell such a good story of what that looks like.


  12. Mark W.
    Mark W. says:

    “These are all part-time,” I tell her. “You will starve.”

    Then we have a revelation.”

    Love the post and the two of you collaborate well together and make a great team. Best of luck to Melissa.

  13. L.
    L. says:

    Can I ask what Melissa’s Myers Briggs type is? I felt as if I was reading about myself (I’m an INFP). Keep up the good work! :)

      • Sophie
        Sophie says:

        Weird, because I am an INTJ (supposedly) and I don’t relate to Melissa *at all* (highly employable, never been fired (at least not yet!) and generally prefer the ‘security’ of working for someone else as it leaves parts of my brain free to think about what I want to do for me rather than worry about a business/empoyees etc etc)

        Also, Penelope, I thought you mentioned a while back that INTJ women usually don’t want children, but I think you’ve also said that Melissa wants nothing more than to be a mom/wife?

        • Tony
          Tony says:

          I am an INTJ and in certain respects very much like Melissa. I have been let go from my last job and have suspected I would have been let go from a few of my past jobs had I not been hard to replace. I am very interested to see how Melissa does since I would love project based work but since I do have a family to support I need the steady income. Good post.

  14. Melissa
    Melissa says:

    Not cool to date or mess around with your fiancé’s best friend. Or your best friend’s fiancé. Or even your best friend’s former fiancé. Not cool. And not a good choice for a partner, for more than one night.

  15. LP
    LP says:

    I feel like I have so much in common with Melissa every time you write about her. 3 years is the longest I’ve kept a job, and it’s mostly because it was in a 100 year old building full of antiques and I could just bask in being surrounded by beautiful things all day while I read blogs.

    I’m keeping my last 5 month job on my resume because a) I did a lot of things related to HR, which is the field I’m trying to go into and b) my job was eliminated and the duties combined with another position that I wasn’t qualified to move into.

    I really like those links to the photos of millennials (my generation) with all their stuff. Up until 2 years ago I felt like a nomad; all my stuff fit in my Grand Am and I was moving once every year. Now my current boyfriend and I have managed to fill a 3 bedroom house full of shit that we inherited from our parents when they wanted to clean out their houses. I like how their stuff is mostly books, and I’d love to get back to that. :)

  16. Irving Podolsky
    Irving Podolsky says:

    Hi again Penelope,

    I don’t mind that your post titles are at times misleading and meant to attract internet attention. I read your articles for their deep content, knowing that generally their focus will be about the quirks of human nature. You didn’t let me down with this one.

    About Melissa…

    You’ve described an intriguing character from a writer’s perspective. I’ve spent years analyzing what makes people tick and I cannot get a lock on your friend. And yet, I am fascinated with her complexity.

    I get the impression from this post and previous ones that Melissa is more of a “sister” to you than a friend and employee. And I think you love her.

    I am moved by your subtle admission of that.

    Your writing makes me concerned for Melissa. You have established a great value for her and yet you’ve painted a tragic heroine. She tears down every bridge she builds and yet so many people yearn to love her, including you. At least this is what I get from your depiction of her.

    I might be totally wrong about this. If I am, tell me.

    But following my current perceptions, what bothers me about this latest “Melissa” chapter, is that I’m afraid she will get fired from her future marriage. Because, marriage is a JOB too.

    One has to feed it, watch it, nurture it, PARTICIPATE within it, and make the wedding day promise the most important light in the sky. Depleting the attention to marriage for the more secure and confined certainty of reading alone will cripple devotion and trust. Getting bored with a sacred union is the end of it.

    Even with a total provider-spouse, both partners must LISTEN as well as being listened to. If he/she does not, if intimacy is relegated to a mattress and an expense account, someone is choosing the role of a sex trinket, roommate, and (with women) breeder of children.

    For some wives, this is a fulfilling life style. Would it be for Melissa?

    If it isn’t, getting fired from a marriage or quitting another one cannot be continually reworked on a resumé.


  17. Chris
    Chris says:

    Hi Penelope – Long time reader, 1st time commenter. Great article. I find a lot in common with Melissa. I work best on projects with a goal, end date. Love the defining phase of what is needed, detail the steps to get to the different smaller goals and then the push towards the end of the project with the success of what done is out and in the world.

    Still trying to learn what is a good way for me to go. I’ve done freelance, consulting, and full time employee. Longer with some success as a freelancer, but finding clients is a lot more work then what I wanted to do at the time. Hope Melissa doesn’t run into that issue.
    Best of luck to Melissa and you. Keep up the great work! – C

    • Penelope Trunk
      Penelope Trunk says:

      Hi, Chris. Thanks for commenting!

      People really underestimate how much of freelance life is spent drumming up business. The best freelancers are people who like marketing more than they like doing the particular skill they are marketing. Because then they’ll definitely drum up a lot of business.


      • Amy
        Amy says:

        I’m terrible at marketing myself. I found that by getting to know potential clients and focusing on those who really resonate with you as a person and the work you do, you can start to rely on referrals. I’m two years in, but finally 100% referral-based and making a full time “corporate” income by freelancing.

        I’m not doing anything particularly unique…just graphic design/web design.

        • Help4newmoms
          Help4newmoms says:

          Amy…don’t sell yourself short. Many folks need exactly your me for example…graphic design is not my thing but I need the service..even though I work heavily in social media. How can I find you?

  18. Dusti Arab
    Dusti Arab says:

    Good for Melissa for making the jump. From someone who is 24 and has had 37 jobs (most of which I would quit after a day or three), I’m not sure there is any career I could stick with for long.

    I’m fairly certain my last employer laid me off because he didn’t have the heart to fire me because I’m really likable. (ENFP) That said, it left me feeling pretty unresolved. Kind of like a bridge not quite burned, but there’s a creepy guy on a horse sitting up there waiting to get. Of course, it’s probably all in my head because I’m overly sensitive.

    Anymore, the guts to stay freelance while I’m still scraping by when I know I could get hired at a tech company I’d quit in a few month anyway is the problem.

  19. Becca
    Becca says:

    This post really struck a cord with me. I’ve been fired 3 times this year- all in a row, and I find myself completely lost as to where to go from here. I’ve come to hate my work (pastry chef) and refuse to go back. I’m also quite certain now I’m unemployable. I would love to work for myself, but the overhead of opening a bakery is quite large and I have zero resources. (And I’m in INFP while we’re all sharing).

    I had e-mailed you a few months ago with my conundrum (because mostly I ultimately want to be a stay at home mom), and you offered career counseling, but unfortunately I was fired (2nd job) that same week.

    I hope to one day figure it out. Ideally in time to pay the rent Feb 1st…

  20. Carl
    Carl says:

    Being employable is more about being consistent and reliable, it’s also about attitude. If you aren’t consistent or reliable you will most likely get fired eventually, certainly not promoted. But then the Meyers-Briggs is the answer to all questions in the universe.

  21. Alison Elissa Horner
    Alison Elissa Horner says:

    This post and the comments really made me think- so thanks for that!

    I can definitely appreciate the idea that being an employee can be a simpler and less time consuming life than freelancing or being an entrepreneur.

    However, I’d note that advancement in plenty of fields entails what I’m assuming you’re alluding to when you say ‘the worst parts of earning a living’, aka getting clients. Off the top of my head advancing to the partner level at a law firm, accounting firm, or consulting firm generally requires the ability to bring in business.

  22. Mr Kaan
    Mr Kaan says:

    Everyone is different, and as you say, some people work better with certain work arrangements.

    Freelancing provides a different kind of freedom to a standard fixed job and can be very demanding, what I find attractive with it is that you receive feedback much quicker (and higher impact feedback) and that you are responsible for your own work to another degree than if you are working at a corporate.

    //Mr Kaan

  23. Flo
    Flo says:

    This is for Steven (the ex-fiance).
    Fortunately for you it didn’t work. Besides her many issues Melissa couldn’t care less for your feelings or well-being if it took 3 days to hook up with your best friend. There are simply no excuses.

    • Daniel Baskin
      Daniel Baskin says:

      Social rules come in many shapes and sizes. There is nothing wrong with breaking social rules. Life is about choosing which ones you want to follow and which ones you don’t, and then accepting the consequences of those decisions. Getting with your ex’s best friend is a social rule you happen hold to. Fine. But Steve, just like everyone else, needs to accept the consequences of getting into a relationship with Melissa. She is not good or bad. She just is who she is.

      It’s actually kind of funny, but INTJ is the stereotypical and by far most common villain mbti type. Often they are crazy or emotionally damaged, but many have valid reasons for being against the protagonist(s). Society sucks and most broad and imposed social rules are stupid, or at least, not sufficiently one-size-fits-all. INTJ’s are just more frequently able to pick up on this, and get ridiculed for it.

      • Sophie
        Sophie says:

        Daniel, do you have a source for your last ‘catch all’ statement about INTJ’s? Because I am one and your diagnosis of villanous and emotionally damaged doesn’t really ring true for me or any other INTJ’s I know (Full disclosure: my sample size is 3). They/we tend to come across more emotionally removed, yes, but also like rules as long as those rules make sense to them…

        • Daniel Baskin
          Daniel Baskin says:

          I miscommunicated or you misunderstood. Either way, no, INTJ’s are the coolest people ever. I just meant that their image to most people is selfish and cold–especially in narrative / media culture.

        • Rebecca
          Rebecca says:

          Hi Sophie,

          I am very close with a few INTJs so hopefully I can help. My boyfriend is an INTJ and we really click because I’m an INFJ so most of our best conversations revolve around analyzing ideas. He is an analyst in a management consulting firm which is perfect for him. He’s really highly focused when it comes to work and can make sense of vast amounts of data and draw conclusions. I think INTJs are good at sensing the overall picture and understanding strategy (N) and then following through on their ideas (J). A few of my female friends are INTJ and they tend to think very analytically and strategically, and are not as prone to make decisions based on emotion (one of them also works in management consulting).

          Hope that helps!

  24. Naz Laila
    Naz Laila says:

    Penelope I read your blog every now and then, so I knew little bit about Melissa before I took ‘your write about yourself course’. Melissa did a great job with that course and every time I heard her voice I kept thinking, “she is such a nice soul but she is lost”. I wish I could explain why I felt this way (I think I spent more time thinking about this than listening to the webinar at that time, because it was such a strong feeling). But it didn’t make any sense so after the third webinar I started to ignore that feeling and told myself ‘ I need to focus on learning how to write about myself not how to explain strange feeling about somebody that I hardly know’. Now when I read this post one thought keep coming to me ‘Melissa need some one to believe in herself and the rest ( job, relationship) will follow.’ No I am not a psychic or don’t have any special power (in fact I am a real hard core science person) , so I feel quite strange and embarrassed. I am not even sure that I will post this comment because I am scared that it will make me look weird and stupid. Then I think what if it is true, what if it helps? I remind myself about the Seth Godin’s last blog post.
    I decide to be out on a limb

  25. The Dame Intl
    The Dame Intl says:

    Wow, this could have been written about me, minus the boyfriend part and your explaining Melissa has helped make so much sense out of myself because we have had the same trajectory. I love how you also explain that quitting before getting fired becomes an art form, my last real job was back in 2005 when I actually got up and walked out and my boss thought I was going to lunch. I just never went back, I had finally realised that I was not cut out for having a boss or a desk in someone else’s workplace.

    Im only just now realising that freelance work is the direction I need to go because I also suck at making money on my own.

  26. Laura
    Laura says:

    Melissa sounds like she has the perfect temperament for freelancing. In my experience, here are two things you need to do in order to be a happy freelancer:

    1. Don’t stress when you have too much work. Remember, it’s better than the alternative.

    2. Don’t freak out when you have no work. Pretty soon you will be swamped again (see #1). If you don’t enjoy the downtime, which is one of the greatest benefits of freelancing, you’ll be stressed every day of your life. During lulls, do marketing and work on your own personal projects until another paying client comes along.

  27. HS
    HS says:

    Melissa comes across as a charismatic, smart, but selfish person. She doesn’t seem to have a lot of empathy for other people.

  28. Help4newmoms
    Help4newmoms says:

    It occurs to me that the very thing that made Melissa a “bad” full time she escapes to read magazine exactly the thing that makes her perfect for her freelance job. I think that is what many of us aspire to…Turning what we do in our free time, things we enjoy, into a profitable enterprise…I am envious.

    Penelope, reading your blog always gives me a renewed sense of purpose and motivation. Could you share with us some of the blogs that you regularly read for inspiration and motivation. So far, your blog is in the only one I’ve got and I would like to add more!

  29. E.S.
    E.S. says:

    I think it’s quite common for intelligent people to get fired. It’s happened to me 3 times, 5 or 6 if I count the “they wanted to but didn’t have the balls to confront me so just let me leave.”

    Intelligent people don’t find joy in working within the parameters and confines of a normal job. They want more autonomy, more ability to be a free-thinker. I would always leave for 2 hours during the day and lunch with a friend, telling myself I’d make it up on the backend. Mostly I just killed time all afternoon.

    Project based work is actually what I advocate that corporate world become – negotiable hours, time measured in work units rather than 8 hour days regardless of how low level one’s job is, longer, more leisurely lunches. I think the 8 hour day, much like the public school day, is dead. It’s dead because it’s dehumanizing and robotic.

  30. Leslie
    Leslie says:

    I knew I was going to be fired even though I had really great performance reviews. The boss had other people in mind for my position so I quit, but not before I had another job lined up. It turned into a series of jobs that became a freelance business. I even freelanced for the people that were going to fire me. The idea that you have to do something wrong to be fired is just not true.

  31. kendra!
    kendra! says:

    Wait–we’re allowed to be a ” project-oriented person”? B-but, I thought? I thought eleventy thousand years of preparatory school was preparing me for being prepared to sit zombie-like staring at a screen for the requisite 40+ hours and Be Fulfilled. We’re allowed to be excited by projects and not so dazzled with interminable agendas that are all part of the larger vision of corporate whatsits where the output is all so unclear and intangible? There can still be success had by the project-oriented?

  32. Sara
    Sara says:

    “Stuck in the middle again…”

    I’m a freelancer because I’ve not been able to secure full time work over the past year of my life. I’m a visual designer with a pretty decent track record, but, since our family relocated to the south for extended family reasons I’ve not been able to re-establish myself professionally here. Although, my networking efforts have resulted in an insane pursuit from a Mary Kay rep who really, really wanted to give me a facial. That didn’t work out either.

    And so, since I have been completely unable to even get an interview in this area, I’ve resorted to sending out my resume to other states in the hope that some type of remote work scenario will emerge….I often get positive responses, but, those doors close when they find out where I live – the question is always “are you moving out here?” Although my plans are not to move, I’ve started responding by saying “I’m definitely considering it.” This gets me farther along. Almost none want any type of remote scenario, though.

    Freelance, project-based, full-time remote with some travel – anything goes. Is there anyone out there who’s looking for an energetic designer that’s worked on everything from brand identity, print collateral, advertising, interactive, and even 3d video health games?? I can share work if you’d like to see it…

    We could lose our home.

  33. tj
    tj says:

    She’s now with her ex-fiance’s best friend? Within days?

    This is going to end very poorly – and the dude is going to be missing his best friend b/c he broke a couple cardinal rules here.

    As for Melissa – why pile on? Disappointed with both of them.

  34. Abhishek Sharma
    Abhishek Sharma says:

    I love it. I’m so happy for Melissa. And I think I should find out what Myers Brigg type the med student is, so you can tell me if we’re a good match

  35. Rachel L.D.
    Rachel L.D. says:

    I’ve been working freelance for 17 or 18 years now, and I honestly don’t think I could ever go back to a regular 9 to 5 job. It’s like the perfect combination of working for yourself, and you have a steady flow of work being funneled to you through bigger companies. You don’t get the burdens of running a larger company and dealing with employees. The only downside is your income is limited by how much work you can do, but I still can’t get myself to do anything else. It’s freedom with a paycheck and it’s addicting.

  36. Miss Britt
    Miss Britt says:

    This is me. I’ve always told myself I could go back into sales if we really needed the money, but the truth is that I’m unemployable too. I’m project based, and I get bored with even great jobs after a few months. I appreciate this affirmation that I shouldn’t go get a job. :-)

  37. Tony
    Tony says:

    I keep studying this post because I am wondering if this is a good direction to take my career. I get bored with some of the IT donkey work I have at my normal 9-5 job but I will take on projects for friends and relatives because the problems they ask me to solve are interesting even though it doesn’t pay much. Once again good post.

  38. Toni Kunz
    Toni Kunz says:

    Love this blog – just discovered it over the holidays…I read this entry a bunch of times and kept returning to it.

    I was employed for 17 years and have been self-employed (in partnership with my husband) for 11. We rely entirely on self-employment for survival – there is no safety-net salary coming in from elsewhere, I did not inherit a family business and I am not wealthy.)

    At the end of the day, my opinion is this: It does NOT naturally follow that “unemployable” people will succeed at self-employment. Without understanding (and owning) the reasons why one either failed as an employee (or succeeded but hated every minute) one won’t get far. The traits and abilities that have served me best as a small business owner are: being a team player (because yes, customers and suppliers still exist in SE), being accountable, consistent, courteous and finding real pleasure in service. Yes, sometimes I want to read a magazine instead of working (I’m a graphic designer), and sometimes I do it. But not at another’s expense. Bright, sporadically effective, charismatic people who are brilliant when it suits them, are often handed free passes on the drudge work. Trust me, self-employment is a mix of both, and humility is essential :).



  39. Karen
    Karen says:

    This is a great post. I hope you will consider putting on a seminar on this topic. I think there are many people who are willing to take the risks of freelancing, but don’t really know how to get started (like me). I think you could also tie it in to you rhomeschool blog – I get the feeling there are many women who’d love to homeschool but can’t see a path to still making some money (which is necessary for many families) and having the flexibility to homeschool.

  40. Easy Freelance
    Easy Freelance says:

    I got here just surfing about freelance sites :) to see what’s the buzz online and i read all the article :) i like how you write.

    ps. one small thing.. :) is Melissa single?

    (ps. 2 joke ;))

  41. Minnie
    Minnie says:

    I’m really torn between freelancing right now and finishing college. I have just under a year left of social work, and where I live in Canada you can make good money and have a secure job doing it. However I hate working for other people, and have always quit my jobs in the past mostly because of morals regarding management (worked in many group-homes). My fiance and I are running a contracting business which is doing really well, and now we want to expand into flipping homes, and I want to restore old furniture – which would be good for the time being because there is a demand for it here as it is trendy, so it will obviously only last for so long. Of course all of this is dependent on the construction industry which tends to have its dry spells. To finish college or not to finish college … I hate sitting a a desk all day learning (not learning) things I can easily teach myself. I need a shove. – Gen Y

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