Advice Mega-Column, Part II: Giant Student Loans, Mean Girl Friends, Whitepapers, Career Changes, and Minimum Viable Products

advice mega post Part I

OH NO! For the last year-plus, a Contact form on our website was not functioning properly. Instead of sending your questions to me, your questions were being stored in a database. We finally figured this out, and discovered a TREASURE TROVE of burning questions! I can’t answer them all, but I can certainly dive in. Enjoy! Read Part I here.

How to handle the situations where an opinionated woman isn’t appreciated because she’s not the regular woman with all smiles and glitter? Like, Hillary Clinton…. Or when same woman is disliked by other women in particular. I seem to bring out the high school in so many grown women, and I am not interested in those kind of fights. And it can really bother me when I am treated like in high school, some women seem to think that smiling while not answering an honest question of “are we alright? Is there anything we should discuss?” but then answering those questions to someone else adding silly voices, that this is them being nice. And if I call them out on it I am mean and ungrateful since she did “comfort” me by answering “noooo we’re good I love yooouu” when I asked. Please write something on this subject! What am I doing wrong and how can I manage these situations without being all hurt and sad?


Wait, where are you meeting these women, in a Garry Marshall movie? I recently watched a couple of old Sex and the City episodes, and even when the writing is good, all four main characters regularly shriek and squeal when one of them appears unexpectedly or a thing happens with a boy. I know a lot of women and this has never happened in my life. When I say, “I got engaged” or “Look, I’m back from Europe!” all the other women I know say things in words, like “Congratulations!” or “Nice, how was it?” Never “Eeeeeeee!” because we are not acting out a teleplay written by misogynists.

Look, from the situations you describe, it doesn’t sound like these women are coworkers. These are your “friends”? What the fuck do you have in common with them? If they’re your family, you’re allowed to disengage quite a bit. Just show up when people are in the hospital and send baby gifts and move on.

Do you need to move to a city with more ambitious people who have bigger things to worry about? Do you just need to be a lot busier so you don’t have any time left for these people?

Don’t spend any more effort trying to fix relationships with people who don’t seem to care about you and who you don’t even like all that much. It’s okay to enjoy your own company. Plenty of introverts consider a full social life to be, like … two friends. Or, if you do want to be around lots of people, there are billions of them in the world. Go take some classes, volunteer, learn to dance, take a Myers-Briggs test and join an online forum for people with your personality type (Are you an INTJ too? I wouldn’t be surprised), go to a convention for something weird you like that nobody else you know is into. Look, maybe you get along really well with crotchety old Civil War buffs. Maybe you want to do some cosplaying and screw what these Mean Girls think.

Put your emotional labor towards making sure this same problem doesn’t hound you at work. If other women seem to dislike you, try to get on top of the situation – do a lot of listening, ask them a lot of questions, use your assertiveness to stand up for other women who are spoken over in meetings. Maybe you’re not like them, but everybody likes to be around other people who make them feel good about themselves. You don’t have to be similar to someone to accomplish that.

I’m glad you thought of me for a question about women who aren’t all smiles and glitter.


Hey Bullish ladies! I came across your article on using white papers for skills development and marketing. I’m looking to enhance our marketing material and am wondering how beneficial something like this might be…and if it’s even still a valid option to suggest in this day and age? Unfortunately, the majority of examples I could hunt down on the interweb are about as dry as you could imagine. I typically write informally (probably not the best way for tech talk, but eh, no negative feedback yet).



A lot of what people called “whitepapers” a few years ago are now “ebooks” or digital downloads that you have to enter an email address in order to receive. That’s fine, feel free to write a free ebook or a special report or whatever you want to call it. But “whitepaper” still sounds meaty and academic. If it does sound a bit old-fashioned, I don’t think that’s a bad thing. I think that intimidates people who write free e-books.

There’s also nothing wrong with an informal whitepaper as long as it provides value. The whitepaper I wrote in 2002 that ended up being used in a graduate level business school class at California Polytechnic as late as 2010 (!) is here. I’m sure the original version had my company name and URL on it — this is the plain version I sent over to Cal Poly on request.

This paper is short, direct, mathy, and something that someone buying online advertising in the early 2000s would have referred back to repeatedly. I also like that it’s not full of advertising. If you read this and you were like holy shit who is the person who wrote this, you’d google me, right? And the business that comes in when people think it’s their idea is always the highest-quality business. If the relationship begins with you in a sales posture, you’re always going to be in the lower position.

Bullish attracts a lot of women who did well in academia, and I think there’s something to be said for going with your strengths. If other people are rehashing their blog posts into beautiful but low-info “content upgrades” (ever downloaded a beautiful worksheet that was just so pretty, but was basically a checklist of five really obvious things you already knew?), it can set you apart to write a paper the way you would have written one in your graduate seminars.

But whatever your style, the idea is to provide so much value that people pass thing thing around to their coworkers and try to hide it from their competitors. Give people a secret weapon! They’ll remember you.


Hey Jen! I have an idea for a side hustle but am unsure of how to proceed in the initial exploratory stages. I live and work in a place with lots of non-native English speakers and my coworkers regularly ask me (as a non-work-related favor) to read through their cover letters, grant proposals, etc, to polish up the language. (These are professionals with very solid language skills — I don’t do much substantive editing, just proofreading and making it sound more natural to an English-speaking person’s ear. They seem to appreciate it, and the fast turnaround I can provide compared to a more involved editing service.) I would like to see if I could do this kind of thing for money in my community, but first I would like to see if people who I DON’T know would be interested, and whether I’d be any good at it outside the context of friends and colleagues. I was thinking of posting an ad offering this service on a classified ads-type Facebook group that exists here to see what kind of response I get, and to learn more about what kinds of specific projects people are in need of. My question is, how do I sound/act professional at the stage when I’m just feeling things out? Is there certain terminology I can use when advertising for “I’m offering this service to see if I might be able to professionally offer this service/to see what categories of projects and rates I might set”? Do I have to do this kind of exploratory work for free, or can I offer steeply discounted “introductory rates”? If I charge any money at all, I assume I would already need to be doing all of the necessary documentation and procedures that go with having a freelance business — so should I go get all of that in order before I’ve even done any work for anyone, much less decided whether this is a worthwhile endeavor? Basically, how do you operate in the nebulous area between “this is a possible idea” and “I am implementing my idea”?


I wouldn’t offer the service for free or at a steep discount – you’ve already done that part. What I would do is ask for a little something from the people who keep asking you to do this for free. For example, “I can do this, but I’m actually putting together a website about my editing service – do you mind if I use a section from your document as a before and after? Of course I’d take out your identifying details.”

Then, ask these coworkers who’ve been asking you to do this work for free for their advice. As in, “I’m considering doing this professionally, do you know where I could find people who would be interested?” You may find yourself making a speech about cover letters at the local Korean church. Maybe parents want to hire you to go over their children’s college admissions essays.

I’d set your rates where you want them. If you say you’re worth $100 an hour, some people may balk, but many will assume you must know what you’re talking about. If you start off at $20 an hour because you’re “just exploring,” you’ve anchored yourself in people’s minds as a $20/hour performer, and you’ll have a hard time getting to $100.

As for your question about documentation and procedures, the key idea of the MVP method is to iterate. Do just what you need to in order to collect information and sell to your first customers. Maybe that’s just a PDF one-pager. Maybe it’s a website with before-and-after screenshots, and a Paypal link for “Cover letter revision, $195.” And then be willing to scrap it all and iterate based on what people’s actual pain points are.

That’s another thing — pain points. Do people really want their cover letter edited, or do they want to get the job they’re applying for? Do they want to write a perfect business email, or do they want to never be embarrassed in front of their boss again?

Maybe editing a cover letter is a stopgap for a deeper problem. Maybe what people want is a business writing class specifically for Indian IT professionals. Maybe what people want is speech and interview coaching with a focus on American social customs.

Fortunately, you already know a lot of people you can start talking to. Keep your focus on solving urgent and pre-existing problems that real people have.


I am currently 32 years old. After a decade’s worth of working in this direction, I am really happy with my current job situation – I’ve earned an advanced degree and recently landed a job that I love; one that pays decently and has plenty of room for growth as I move forward in my career. Unfortunately, due to a series of terrible and uninformed financial decisions made in my 20s, I also have a student loan debt the size of a mortgage. (With interest, it’s currently over $400K and counting). It’s been only in the past few years that I’ve discovered I have an interest in business and entrepreneurship, and would really love to develop these skills (initially as a side hustle, but one day as a full-time gig), but I’m not sure if that’s realistic given my age and my financial situation. I have no money to invest in a new project, barely any savings, and can’t afford to take a financial hit and go further into debt if a fledgling business were to fail. At the same time, I feel that I need to “think big” if I’m ever going to get out from underneath this crushing debt and not just let it soak up huge chunks of my paycheck for the rest of my life. I’d love any advice you have for ambitious women who have a financial past that’s haunting their careers. (If it matters, I’m child free and not planning on having kids, so that’s one big expense/responsibility that I don’t have to plan for at least!) Thanks in advance for your thoughts!


Oh my, $400K is a lot of debt. Over 30 years, that’s $2,400 a month or so? That’s a tough situation. But you’re hella educated and employed, so that’s good. Stay bullish!

On the savings side, you could live in a communal living situation or a tiny house or who knows, but I think it’s sometimes easier to change your lifestyle radically than to make smaller changes, like the apartment that costs $100 a month less but is kind of dingy and sad. Instead, you’re like, I love living a rustic lifestyle in this cabin where I have a place to think and a woodstove to maintain.

But there’s only so much you can save, and you’re probably already doing a lot of that now. If you make $80K a year, you could theoretically save 100% of it, if you lived with your parents, ate their food, and walked to work. You still have to pay taxes.


It’s not easy to develop a business that generates $100K a year, but it is at least mathematically possible, whereas saving that much is not.

What can you offer to very wealthy people? Start there, because 1) you don’t have time for trivial shit, and 2) you don’t have money to invest. If your advanced degree is in clinical psychology or any kind of personal counseling, are you able to create a 10 week program for CEOs to reduce stress? CEOs. Seriously, if you say it’s only for CEOs, people who aren’t quite CEOs will want it even more, and try to convince you that they’re eligible to pay you money, even though they’re VPs or their dad’s the CEO or whatever. Wealthy parents pay over $1,000 a day for their children with drug and alcohol problems to have sober companions. You can’t just start randomly doing that, of course, but I mention it because rich people have many of the same problems as everyone else, but they can pay more for solutions.

Whatever you decide to offer, make sure it’s about the client’s pain point and how you can solve it. It’s not about you. And make the offering so irresistible that you can sell it directly in an email. “As a clinical psychologist, I’ve developed a program that helps working women accomplish 100% of their to-do lists while reducing stress.” SOLD.

Those are some off the cuff ideas, and I don’t know exactly what your area of expertise is. Selling directly to the wealthy is a fine starting point. You have to meet wealthy people and earn their trust, which means not hating them on sight. Work on that if it’s a problem for you. And get clever about meeting people. I’m sure you have alumni groups from all your universities. Also go to events on investing. Many of these events are both free and attended by multimillionaires. Sit through a presentation about hedge funds. Learn to get comfortable. “I’m a social worker with a focus on special needs children. I’m just getting started with investing. How long have you been coming here?” Meet people. Figure out what they need and, eventually, what you can provide.

There are lots of other ways to start businesses with no money down – create online courses and ebooks, for instance – but given your circumstances, why not aim for large quantities of money right away?

Finally, address your situation head on. Find an online community of debt hackers, and look for any (preferably free) counseling. This article suggests that you may not want to put any additional money you’re able to make towards immediately paying down your loans – you probably want to build an emergency fund, for instance. The article also features a guy who figured he could make a better return investing than paying off his loans (if your loans are at 3% interest but you can get 10% on your money…).

You might consider making a job change so you can qualify for a student loan forgiveness program – this takes at least ten years, after which you could go into private practice or anything else you wanted, with your debts forgiven. And apparently the new income-based repayment plan (thanks, Obama) “caps your monthly payments at a ‘reasonable percentage’ of your income (determined by the federal government) and forgives any debt remaining after 25 years.” Don’t try to put this debt out of mind – you should be the expert on these programs – and also make a plan to save for retirement.


Hello Jen, I’ve got a bullish question. I’m currently working at an office with a relatively relaxed policy towards working hours (as long as the job gets done, we can schedule personal stuff into the day, or work from home, if needed). But it isn’t my dream job, so I’m trying to make a career shift within a few years. The plan is to acquire some new (more quantifiable) skills in the meanwhile by going back to school starting September this year. Unfortunately, these skills have nothing to do with by current job. So now I’m trying to figure out, how to convince my boss, that I should be able to work from home and/or more flexible hours (early mornings, late afternoons 2-3 days of the week, when I’ve got school) on a regular basis, without letting them realize that I’m plotting to change careers. Could you please give me some advice, how to present this to my boss as a positive, mutually beneficial thing?


Hmmn, sneaky. Why not start with a class that actually is related to your job – and, ideally, to your new profession as well? I mean, everybody needs Excel, or project management or something, right? Get approval for something job-related, settle into your new schedule, and the 12 weeks of your project management class will go by quickly and then you’ll just subtly switch to Ruby on Rails without saying anything to anyone. If it comes up, try “Oh, I learned so much from Project Management I just started looking at other courses that were offered, and now I’m trying a coding class.” Like you’re just personally intellectually interested in things. Curious like a cat. Not like you’re scheming to get the hell out of there.

Back up this plan with totally nailing your job responsibilities! Increase the amount of documentation in order to cover your ass. Report completed tasks and successes to your manager or record them somewhere. Check in frequently with your boss. Anticipate her needs and get things done without her having to ask. Earn yourself the benefit of the doubt.


Hi Jen, I have a “bridge job” question. Currently, I am in the midst of leaving a copywriting position to move to a new city. Like all copywriters, I have several half-finished novels I’ve been plugging away at this year. My dilemma: Part of me thinks it might be a good idea to get a part-time “bridge job” when I move to this new city, doing something I enjoy that is more active than office work, such as working with plants or at a daycare. A less demanding job would be useful in terms of lowering my stress level as I try to acclimate to my new environment. In addition, I could take this opportunity to finish these darn novels without copywriting work sapping my creativity. On the other hand, I am also tempted by the prospect of doing higher-level, better-paid copywriting work than I have been doing in my small city. This larger city offers that possibility, and part of me thinks it would be foolish to squander my momentum with a bridge job. A higher-paid position could also afford me some more financial security, which–let’s face it–also lowers stress considerably. I could address certain life situations with said financial security, which would improve my life in the long-term. On the third hand, maybe I’m thinking too small. Why can’t I start my own copywriting business and set my own hours? I’ve done that before, albeit half-heartedly. Hustling your own clients, however, can be time-consuming and “feast-or-famine,” money-wise. Eventually, I might build enough momentum to be self-sustaining, but I worry about the client hustle taking up so much energy that I don’t have time for the more creative pursuits that I’m actually passionate about. Your advice?


Funny kitchen sponges and birthday items on the GetBullish store


I think the key to your question lies in the phrase “finish these darn novels without copywriting work sapping my creativity.” You can only go hard on one thing, and you don’t seem to know what that thing is – but at least you know there are limits to your powers. There are, for all of us.

You want to finish your novels. You want a high-paying job in the city. You want to start your own business as a copywriter.

For each of these, ask Why? Do you want to be a novelist? Do you want to be a business owner? Is “copywriter” an important part of your identity, and if so, are you open to that changing?

Do not start your own copywriting business. You’re right about spending all your time hustling, the feast and famine cycle. You know why people go through that? To build a business that someday runs on its own, so they don’t have to do that anymore. A copywriting business where you, personally, do all the copywriting is not scalable. It cannot grow beyond your personal ability to hustle and churn out copy. Furthermore, every job you do for a client is unique. You can’t do something once and then profit from it on an ongoing basis. That is a shit business. It is doing 2+ jobs at once, with no endpoint, no big payoff.

You mentioned “working with plants or at a daycare.” Why not get a high-paying job as a copywriter – let someone else hustle up clients – and start a daycare, or a plant nursery? You could end up owning a chain of daycares and raking in millions of dollars. That’s scalable. Maybe you use your love of literature as a selling point, like it’s a daycare that’s really focused on literature or storytelling or something. Or… just a regular daycare, I mean, honestly, people need daycare like they need air. Keep their kids alive and happy and you don’t necessarily have to innovate, even. Sell people something they desperately need and will pay all of their money for, like daycare. Not like copywriting.

Don’t start a business that’s just a way to give yourself a shitty job. Start a business that’s a way to create good jobs for other people, or a way to create a system that works without you selling your time by the hour (that’s a job). You could create an online course (and/or a Kindle book) about how to become a highly-paid copywriter. You could write a novel, and then write a how-to book about how to write a novel while working a full-time job. Go shop around the novel, but in the meantime, but the second thing up on Kindle Direct Publishing and make recurring income. Maybe you create a clinic for high school students to develop their college admissions essays, and you systematize the process so that all the other copywriters are coming to you looking to pick up some extra work at your clinic.

In sum: Go get that good job. If you want to just work and be happy and write novels on the weekends, cool. If you want to start a business, don’t put yourself through the pain unless you’re growing something.


Hi Jen, This is the second email I am sending of this nature: to thank you. I am officially considering myself a bullicorn and honestly- it’s a game changer. I work in a helping profession and they teach us a lot about clinical skills and not so much about business skills. I already have like 10 ideas to diversify my income stream that are in a google doc called BULLICORN, and have taken some actions to achieve those ends. It feels amazing. And also- THANK you for helping me realize that I wasn’t consistently following through on all of my mentor’s advice (without a good reason), and how fucking rude that is. When I spoke to her yesterday I specifically said: I did X, Y & Z, thank you for suggesting it! And then it led to next steps and my mentor became excited, I could hear it through the phone, and then she offered me advice and next steps and invite to join her at a conference where I will meet other people who I can learn from. THANK YOU THANK YOU THANK YOU!!!!



p.s. Join me in September for the 2016 Bullish Conference, a retreat-like event where I’ll be teaching and coaching, and there will be bikinis and mojitos. Gentlewomanly living is happening.


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