How to Succeed at Business Without (kind of) Even Trying


Tod Kelly

Tod is a writer from the Pacific Northwest. He is also serves as Executive Producer and host of both the 7 Deadly Sins Show at Portland's historic Mission Theatre and 7DS: Pants On Fire! at the White Eagle Hotel & Saloon. He is  a regular inactive for Marie Claire International and the Daily Beast, and is currently writing a book on the sudden rise of exorcisms in the United States. Follow him on Twitter.

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33 Responses

  1. Avatar Saul Degraw says:

    The first point about the musician or rock star is very accurate and probably translate to a lot of careers in the arts. There is a documentary called something like “Aren’t you that guy in that thing?” The documentary follows a bunch of work a day actors and interviews them about their careers from high points to long dry spells where they got no auditions and were going into debt/bankruptcy and looking at leaving the industry. I would tell acting students that they would be lucky if this was your career.

    That being said, I think there were always careers that people went into for the money they provided over the love of the field or the reasons for going into said field were always supposed to be about profit.
    Art theoretically has psychic gains. I’ve heard plenty of artists say variations of “I never made much money but I did what I loved.” The same goes with lawyers in certain fields (public defenders and legal aid lawyers come to mind), social workers, and doctors in certain fields, and people running businesses like bookstores and coffeeshops allegedly. I don’t think I’ve ever met an investment banker or finance adviser who said “I never made much money but I did what I loved.”

    I don’t necessarily think there is anything wrong with picking a field because it is supposed to be financially lucrative or at least provide a middle class lifestyle. Our entire government policy in education seems set up to provide students with the skills to get middle class or above lifestyles/incomes. Whether it should be or not is another question.

    I do have a numerous image of a guy who does investment banking during the day and then becomes a barback at night though because barbacking pays the bills.

    What is your advice for the somewhat introverted? I am told I deliver good product at a reasonable price when I’ve done freelance assignments for lawyers but my issue is that I am not out there bagging doors all the time, going to court, introducing myself with shameless promotion, doing CLEs for the BAR to network.

    All that stuff makes me a bit anxious because I am very comfortable with just getting assignments, deadlines, and doing what I need to do. This is also the part of me that enjoys sitting with a good book instead of going to a really loud club. I do like socializing but in one on one situations or small groups.Report

    • Avatar dhex in reply to Saul Degraw says:

      go work for a not for profit in a semi or non-legal capacity. get at least some of the security you so obviously crave, worry less about having to hustle, make less money than you would in the private sector.

      bada bing bada boom

      zee life, zee is beautifulReport

    • Avatar aaron david in reply to Saul Degraw says:

      I think your answer to these questions lies in the fact that you have both a JD and an MFA.Report

    • Avatar Citizen in reply to Saul Degraw says:

      I have read repeatedly read that you value the theater. Have you considered writing theater grants or finding a legal niche that puts you in that realm?Report

    • Avatar Tod Kelly in reply to Saul Degraw says:

      @saul-degraw “I think there were always careers that people went into for the money they provided over the love of the field or the reasons for going into said field were always supposed to be about profit.”

      True, but I’m trying to say something slightly different. I’m trying to say that even most of those people didn’t actually go into it for the $, but rather for some kind of lifestyle and personal identity they assumed money would provide. (And FWIW, they are usually wrong about this.)

      And I think that at their core, most people who go into the non-profit world or the arts are doing the exact same thing. And if you can unpack what exactly those things are for yourself and start asking other people what other kinds of careers provide those same things you crave, you’ll see that there are actually a ton more options than the one you thing is *the* way.

      “I don’t necessarily think there is anything wrong with picking a field because it is supposed to be financially lucrative or at least provide a middle class lifestyle.”

      Me niether. In fact, I’m sort of the ultimate example of that. I never went into risk management because I was passionate about it. I *become* passionate about it over time as I become really good at it, but when I took my first job in the industry I did so assuming I’d be doing something else in a few years. I just needed a paycheck.

      “What is your advice for the somewhat introverted?”

      To pay attention to either the degree to which you think you can become more extroverted or the degree to which being introverted in any particular career or job will still allow you to be successful (for your own definition of success) and happy, or both. And I’d underline that advice quite a bit for you, seeing as you you’re strongly considering going into business for yourself.

      It’s 100 times harder to succeed as a new business owner if you’re not able/willing/comfortable being extroverted. The good news is that, at least in my experience, introvert/extrovert are largely roles people have historically placed upon themselves, usually due to family cues. An introvert can learn to be comfortably extroverted and vice versa, or at least they can in most cases.

      The other bit of good news is that even if you don’t want to be extroverted, there are ways around that. The most obvious is to either hire or partner with someone who is extroverted, and then divide up the responsibilities so that you can handle the details that make your company execute while he or she can handle making sure money comes in through the door. That’s really the best of both worlds for a new start-up: one person who can make it rain, one person who can make good on the promises of the rain-maker.Report

      • Avatar Tod Kelly in reply to Tod Kelly says:

        Oh, and also this: Don’t make the error of falling for the Scott Adams Fallacy, which is an all-too common misstep that most talented introverts do when they become business owners.Report

      • Avatar zic in reply to Tod Kelly says:

        To build on this most excellent point (hiring someone to balance out your skill set,) that someone doesn’t need to be a full-time employee; most particularly in the new gig economy. Small business (and large, too) routinely hire pay-roll companies to help with their HR duties. I’ve a good friend that works as a consulting CFO for numbers of small businesses who’s onwers have neither skill nor inclination to do that work. Accounting is another example of skills commonly outsourced. When I opened a coffee shop, I hired a marketing company to assist with branding and help put the brand out there in the appropriate markets.

        The real task here layered. First, you have to identify the things that need to happen to have a chance at being successful. Second, you need to identify two subsets of your own ability; first, do you have the skills required to do the task in question? (If not, than outsource it, obviously,) but as important, are there other tasks that would produce better return, and so be a better use of your precious time? Sometimes, business owners lose money because they don’t recruit help to do things, and so waste a lot of time that could be better spent, and produce greater return, elsewhere. Once you’ve identified your business needs that should be outsourced, the last step is to find the resources to handle those things for you; and generally, networks of other, similar businesses, are the best resource to turn to to identify the potential consultants and businesses.Report

      • Avatar Saul Degraw in reply to Tod Kelly says:


        I am pretty much in agreement with what you wrote but I don’t know what the Scott Adams fallacy is.

        I can be extroverted in many situations but they tend to be official or known in intentions. The reason I like on-line dating over trying to chat with a random woman at a bar is because on-line dating is explicitly about finding a romantic partner and you’ve done some ice-breaking by the time you meet. Though sometimes this has problems when the gaps in your head don’t meet reality.

        I’m pretty good at networking events. Knocking on random doors (as has been suggested to me because it is “old school”) freaks me out but this could be self-imposed as you noted.

        “Tue, but I’m trying to say something slightly different. I’m trying to say that even most of those people didn’t actually go into it for the $, but rather for some kind of lifestyle and personal identity they assumed money would provide. (And FWIW, they are usually wrong about this.)”

        I can kind of see where you are going but I am nut sure I completely agree but my disagreement could be historical-cultural. Jews went to law and medicine frequently because we were denied entry to business. Law and medicine ultimately became seen as being more intellectual ways of earning a living. So there is a status in being a lawyer in Judaism. Stefan Zweig can wrote in his memoir about how Jewish people really want respect through scholarship and book learning over riches and the getting rich was not an end but a means to liberate yourself and your children so you and your children could then become scholars. So there is some tradition going on here.

        FWIW I might have some of the only parents who would have been disappointed if I ended up a business major or an MBA. I was encouraged and expected to show mastery of an academic field or at least an advanced level of understanding and my mom’s attitude was that business degrees did not count as being academic.Report

      • Avatar Tod Kelly in reply to Tod Kelly says:

        @zic “that someone doesn’t need to be a full-time employee; most particularly in the new gig economy.”

        This is certainly true, but unfortunately for Saul “rain-makers” generally tend to have the kinds of self-identities that don’t lend themselves to being your part time help. There are some, of course. But most people who are really good at making it rain that I know want a piece of the pie.

        @saul-degraw “I don’t know what the Scott Adams fallacy is.”

        I really need to post all of these in one place some day. The Scott Adams Fallacy — based on a gazillion Dilbert cartoons, obviously — is the assumption that people who sell and/or market your product are somehow an obstacle to your success, and that customers who explain they want something different than what you are offering them are stupid.

        As for the rest, I think you *are* agreeing with me: You’re explaining that the reason you (and perhaps other Jews) gravitate to certain fields are reasons that are not inherently coupled with those jobs. As best I can tell from what you’re telling me here, you aren’t necessarily looking to be a lawyer — you’re looking to be someone who is seen as a traditional and/or academically acknowledged and/or approved by your dad (or the greater Jewish community).

        That’s not actually the same as practicing law. Practicing law is simply the vehicle you decided you might use reach that particular goal from whatever Point A you were once standing.Report

      • Avatar Saul Degraw in reply to Tod Kelly says:

        @tod-kelly @zic

        FWIW I’ve approached friends who are in similar employment predicaments and other people who feel stalled in their legal careers. Everyone seems intrigued in frequently but turns me down about starting a firm with some excuse but needing income right-away for daycare or having student loans and no money (not that what they are doing now is exactly bringing in dollars) and other excuses.

        I am also not quite sure how much the “gig” economy is a thing or not. I’ve seen the phrase used enough. I am probably part of it right now but there are still plenty of examples of people with traditional jobs with salary and benefits and everything. Are there estimates about how much gigging is going on?Report

      • Avatar Tod Kelly in reply to Tod Kelly says:

        I think there’s been an increase, sure, but I wouldn’t assume a culture shock is just around the corner.

        Most places where I’ve seen the gig economy take hold fall into one of two categories:

        ** Industries that are really focused on doing temporary projects, like computer programming. I think gig-econ is actually a better fit for these kinds of industries. (In the same way that a framer or a roofer can’t just constantly keep a staff of 40 framers and roofers no matter what projects they’re working gone and stay in business.)

        ** Industries where it has been historically difficult to terminate unproductive, unwanted, or disruptive employees, either due to law or tradition. Think: College professors, for example.

        But outside of those two categories, most industries really need a stable workforce in order to compete.Report

      • Avatar Saul Degraw in reply to Tod Kelly says:


        I suppose law can fit into both those categories but I generally think you are right in your observations. Though I don’t think going year to year as an adjunct is going to make scholarship very attractive to many people especially at the sub-par wages it pays. I can see why getting rid of tenure might be attractive to universities but the fact that it was decreased with a massive decrease in pay is interesting. The other thing that seems popular is to use contracting services. A lot of food workers and janitors in place are now employed by an outside agency instead of the institution itself.Report

      • Avatar Will Truman in reply to Tod Kelly says:

        A lot of food workers and janitors in place are now employed by an outside agency instead of the institution itself.

        Which is not always a bad thing. These contracting services provide a great jobs warehouse. One place needs to cut back (or goes out of business), they might have another place to immediately put you if there is an opening available, which can be a lot better than having to look for a new job yourself.

        Tangential, but not unrelated, I remember when I worked at a fabrication plant. Sometimes they’d have two shifts working a combined hour days seven days a week, and then a project would finish and they’d need to let a bunch of people go and they’d keep a crew on and try to find 40 hours worth of work a week for them to do. I remember thinking at the time that this sort of thing cried out for an employment service (or a union) who could line people up at your door when you need them, and then would find some other door when you didn’t need them anymore. And they could keep their insurance benefits, among other things, from one job to the next, instead of having to change each time.

        I assume that there was a reason this didn’t happen in this particular case, but I definitely see upsides for workers in addition to management.Report

      • Avatar Mike Schilling in reply to Tod Kelly says:

        I would call that the Sports Night Fallacy, I love that show, but the warfare between the lovable, talented Good Guys that did the TV show their way, and the Evil Suits that wanted it to have decent ratings and make some money was just plain stupid.Report

  2. Avatar dhex says:

    i like this quite a bit. it’s what those terrible essays promoted on linked in should be like.Report

  3. Avatar Jaybird says:

    I read an essay a while back from Scott Adams in which he explained that, to be really, really, really rich, you have to be the best in the world at something (or almost the best in the world). Like Kobe is at basketball.

    If you aren’t the best in the world at something, and you’re probably not… you’re here… you can feel better that you can make good money, if not really really really rich people money, by being merely pretty good at three or four things.

    If you are pretty good at writing ditties, creating powerpoint slides, and talking to strangers… you can get a job at an ad agency.

    Figure out the three or four things you’re pretty good at, figure out what job requires that sort of thing, you’ll be able to make a living.

    Sometimes I wondered how I ended up where I am… but I read that essay and it explained it to me.Report

  4. Avatar Burt Likko says:

    My caution after reading this marvelous essay is that each of these four steps is harder than they seem.

    Part one is going to be hard for the young and inexperienced, because it will be difficult to see past the dazzle of the rewards and the lifestyle of the work and understand what the work itself is all about. It’s also hard for those who are advanced in their careers, because by the time one’s frustration builds to a boiling point, it’s much easier to define what you don’t want than what you do, and that’s easy to define oppositionally to recent bad experiences.

    Part two is going to be hard for both the young and inexperienced and those of more career advancement looking to switch.The young and inexperienced probably do not have a good grasp of the kinds of skills that they possess which are actually the marketable ones that employers seek. It will be difficult for those who have been doing something for a while, because it becomes difficult to see yourself employing your skill set outside of the profession that you are currently in. The example of the family law attorney is a very good one. It’s easy to fool yourself into thinking that you have a set of skills so particular that they will not transfer.

    Step three is hard because this involves entering the labor marketplace without a map, compass, flare, or landmarks, without any of the traditional means available for seeking a position or even signalling that a search is underway. A Great many people may not even realize that what you are doing by networking with them is looking for a new place to work unless you tell them so.

    And step four is hard because in these informational interviews, it becomes very tempting to overtly ask for a position, define a position that might be created for you, or ask what positions are known to the interviewee to be available. The interviewee, in turn, probably wants to be helpful and understands or at least empathizes with the anxiety of someone looking for a new spot in a career trajectory. So it becomes tempting to both parties to immediately move to a discussion of what kind of job the seeker will get, and with whom.

    All of which is to say, the advice here is really good. If executed properly and thoughtfully, it is well calculated to land the seeker in a job producing substantial hedonic compensation. I’m just not sure that it counts as advice which one can execute “without really trying.”Report

    • Avatar Tod Kelly in reply to Burt Likko says:

      @burt-likko “My caution after reading this marvelous essay is that each of these four steps is harder than they seem.”

      Oh, this is absolutely true. If I had it to do over, I would title the post How To Succeed In Business without (seemingly) trying. Also, this post already came in at about 2,500 words and so you do what you can with the space. But really, any one of these steps could have been a 2,500 word post.

      Regarding Step 1: I agree. When I am coaching someone professionally, I usually advise them to get away for a day without interruption to do the sitting down with pen and paper part. And even then, I think it’s a good idea for one to go over what they come up with with a trusted partner who knows them well, be that a spouse, bf/gf, sibling or good friend. It also shouldn’t be a temporary task. I think it’s worth going over that question in your mind periodically at any stage in your career, even if you’re happy at the moment.

      Regarding Step 2: That’s why I never believe that this is a task best done by one’s self. I always recommend it being something you process as a dialogue between people who know you well outside of work as well as people who work with you. They are all biased, of course, but collectively they are usually more accurate about what your marketable skills are than you are.

      Regarding Step 3: It’s true that a great many people may not realize that you are looking to work with you, but I think that’s okay. Like I said, you’re not actually trying to trick the people you are networking with, you’re trying to learn about them.

      My problem with what’s become of the phrase “informational interviews ” (well, *one* of them, anyway) is that it has largely morphed into meaning “a backdoor job interview,” which is not what I believe it should be. When you do a FOI with someone, your primary thought process shouldn’t be, “Can I get this person to hire me?;” rather, it should be “Do I really want to work for this person if and when they do offer me a job?” It’s a subtle difference, but it’s really important. (And as a bonus, it leads you to ask the kind of questions and have the kind of dialogue that makes you more appealing to someone looking to hire.)

      Regarding Step 4: Yeah, that can be temping all right. But it’s a temptation worth fighting, IMHO.Report

  5. Avatar Lyle says:

    Interestingly the largest group of professional musicians in this country are likely all part time. Church Organists. In general they are paid since they do have to show up every Sunday. (My sister has done this off and on during her life). So to have access to that track one needs at least piano training. Of course one does have to have a real job to go with it. (Some churches may have paid choral directors also and of course at large churches this at least might become a full time position).Report

  6. I have another piece of advice:

    Be prepared to start at the entry level and to work a job that you might think is beneath your training or education level. If you can’t get an entry level job in your field of preference, get one in another field, do a conscientious job at it, and use it to cultivate skills and references.*
    I can think of a lot of reasons why this advice might not always work, or why it might work for some rather than for others.** One can get trapped in a “lower” job. My also potentially runs against Tod’s starting caveats. And for the record, I do believe that the “drone-like” jobs and call-center jobs can be a starting point to something better. But I think

    *One of my “skills” is to be good at customer service, which comes in surprisingly handy for jobs that one might not think don’t require it. I’m not perfect at it, to be sure, and sometimes a “customer service” mindset isn’t always the right one. But my experience has taught me to work better with people than I would probably have if I hadn’t had those customer service jobs.

    **For one thing, it relies in part on someone else “recognizing” your strengths, and it’s harder for non-whites, non-males, to get that type of recognition than it is for others. My current job–which is a contingent position and may or may not pan out in the long run, but certainly meets my criteria for “meaningful” and “well paying” work–I got by “proving” myself when I started at a lesser position. However, I sometimes muse that if I had been a woman, or black, I might have done the same work, and not been recognized for it. It’s not that my supervisors are racists or sexists, but that there are probably unstated and pervasive expectations that are hard to shed.Report

  7. Avatar Citizen says:

    There can be a real problem in step 4.
    In my experience I have noticed there can be a local position/problem that is near impossible to resolve. My skill set tends to have people push me torwards the position that needs “The Big Fix”. For a couple months I pick through the wreckage and find the parameters that are creating the perpetual barrier/deficiency/moneypit. The parameters and possible solutions are reported and the canvas is set to for the response from management. Almost invariably the report is shelved because the organization/entity is not at a point to either accept/reveal that the parameters exist, or are willing to deploy/accept the possible solutions.
    Those positions are somewhat of a meatgrinder, revolving door for the unaware.Report

    • Avatar Kim in reply to Citizen says:

      Ahh, the wonders of being a corporate analyst!
      You need to learn to embrace your inner asshole, and see if that helps get mgmt moving.
      If not, relax under the knowledge that you’ve given some decent shmuck cover for “why things didn’t go right”

      Of course, being a subcontractor — “the revolving door” is part of the lifestyle.

      If that’s what you want OUT of… well, maybe try getting in at the ground floor (or finding managers who really want Big Ideas)Report

      • Avatar Citizen in reply to Kim says:

        I try my best to stay away from corporate, mostly industrial and civil.
        On the industrial side my label is industrial engineer, but most days I cringe at being called an engineer. On the civil side my label is civil engineering tech3 to avoid all the accreditation/cec/licensing stuff that is constant PITA for the Professional Engineer guys.

        The revolving door is for the unaware. I don’t subcontract, but will fulltime it for about 3 years. By that time I have either succeeded, made progress, or not.Report

      • Avatar Citizen in reply to Kim says:

        That should read Professional Engineer guys and gals. (my last gig had more P.E. women than men) Damn smart women.Report

    • Avatar Tod Kelly in reply to Citizen says:

      @citizen “In my experience I have noticed there can be a local position/problem that is near impossible to resolve. ”

      Oh, most certainly. There are always problems out there that are unsolvable, and there are a lot more past those that *you* can’t solve. Fortunately, building the perfect mousetrap is not the only way to land a great job.

      For one thing, most industries have more than on headache they are trying to deal with, so you don’t have to be they guy coming in to solve the Big Bad.

      But more importantly, most people in charge aren’t just looking for someone who can solve their problems; they’re also looking for people who can bring a different perspective to those problems and their potential solutions.

      For example, take Saul (since we’re all talking about his career this week).

      Were I not retired and Saul were to have walked into my office on a FOI, I don’t know that he could have solved any of what I thought were problems with either my industry, or been able to pitch something I didn’t already know about the risk management services we provided. But if we’d had a long enough conversation and kept in touch, it’s hard to believe there wouldn’t have been a problem I didn’t even knew I had that I might have hired him to help me with.

      Like, he couldn’t change employment laws to make things easier for my clients, but his training might have allowed him to make our risk-managment services tighter — by which I mean reduce the chances that, if used as directed, a company might be sued (or sued successfully) by an ex-employee. Or maybe we use him as a source of revenue, as an in-house subscription service so that for basic employer law questions our clients can get legal advice they trust without having to pay $150 an hour every time they want to terminate an employee. Or maybe we hire him to do that and don’t charge anyone anything, but build part of our marketing around the fact that we do offer his services for “free” as a way to dislodge potential clients away from their incumbent risk management firms.

      There are probably a bunch of other ways that we could have used Saul. But none of those ways would have been anything we would have ever had a job posting for, because “what can we do with a spare attorney?” wouldn’t have been a question we’d have ever had time to have asked ourselves had he not sat down with us.Report

  8. Avatar Kim says:

    I actually did know a guy who found financial chicanery to be a really fun and amusing game… while he was in college. (Find the best way to write off this corporate jet). Apparently, understanding that “this has real world consequences” got to him after a while.Report

  9. Avatar Kazzy says:

    Re: #2

    My supervisor and I are currently working to identify the less obvious skills that people bring to our school and how these contribute to success. So, yes, being a good math or English teacher is important. But so is having someone who can be a “big picture thinker” and someone who is a “details” person (and gangbusters if the same person is both). Being able to “look on the bright side” is a skill and its presence can be a real difference maker. Similarly, being able to look at something that is otherwise working pretty well and say, “I think we can do this better and here’s how,” is a skill. Organizers. Idealists. Realists. “Bringer-togethers”. Etc.

    These are the skills which people often ignore because we tend to see them more as personality traits — which they certainly are in a way — but they are still skills insofar as they are A) able to be strengthen, refined, and developed and B) are valuable assets. We’re encouraging everyone to think of skills in terms of verbs instead of nouns. “What do you do here?Report