Bullish Life: Starting a Business After a Break-up

Hi Jen,

So my boyfriend basically dumped me after Thanksgiving, and I have spent a lot of the week reading your articles, like (off the top of my head) the one on breaking free from terrible situations, the one about the 3 romantic mistakes young women make, responding to disappointment with awesomeness, motivating yourself to be motivated, and of course the one on breakups.

Thus, I am channelling all this energy, while I’m numb, to starting a pet project! That will generate cash! And since you just wrote a column about business ideas, do you have any in your bazillion list that will only involve a blog to start it off? And where I can remain anonymous-y?

Here’s an idea I have — social media for busy rich people. They need blogs, twitter, etc to manage their brand. I like to think (I write better than this email! Promise!). I can set it up for them, edit their blog posts, write their posts, manage their social media for them.

Any others? I just need to do something or I might go crazy! And hopefully, that something will let me have some extra moolah, so that I can go on more dates! 🙂

– Plucky Young Person


I added links to the above letter, and made one correction, Plucky Young Person accidentally wrote “responding to awesomeness with disappointment” rather than “responding to disappointment with awesomeness” which I think really sums up the feeling of getting dumped.

So, PYP: I love that you’ve kind of answered a lot of your own question by looking up some Bullish columns and doing what they say! It’s very flattering, and I’m glad you have a plan! The thing PYP wrote about “channelling all this energy, while I’m numb, to starting a pet project after a break-up is, I think, a reference to this suggestion in Bullish Life: Breaking Up Is Hard to Do:

Grief can be helpful. It drowns out a lot of other things, like muscle soreness from really solid exercising, or boredom from monotonous forms of work. Go organize all the receipts for your taxes. Run. Take the cat to the vet. Do 500 calf raises. Make flashcards of French verb conjugations. Grief will numb you to the little trials and boredoms that bog down happy people.

Just do really productive, somewhat-boring things repetitively and stoically in order to improve your life, so that when you feel better, you’ll look around and say, “Holy shit, the sun is shining again and my job is amazing and I can do six pullups in a row and I speak French?”

So let’s talk about business ideas, which are a nice palate-cleanser after whatever happened with that dude.


So, making money from a blog only is pretty tough. If you google “make money blogging”, you’ll find tons of scammy articles about affiliate programs. Blogging has become incredibly professionalized over the last decade; in 2004, I posted random shit to Blogger all night long, and now I have deadlines and an editor when I write for sites like TheGloss. At some blogs, there’s an editorial calendar where things are planned so far in advance you’d think they had to chop down some trees and print the thing on paper.

Some fashion and style blogs at least generate free stuff (dresses, beauty products, occasionally a trip to somewhere to write about something). But it’s a tough path from there to real sponsored content and ad revenue. To me, it seems like a very indirect way to make money.

However, there are, of course, MANY businesses that involve you providing a service, which you advertise through a blog and other social media. That’s different. I’ve been blogging in various places since 2004, and never worried much about pageviews; my personal blogging has always been for the benefit of a small group of important people. I’d rather get 500 pageviews and a paying gig than 100,000 pageviews from teenagers who type “bitch” in the comment box.

You can also try e-book publishing if you have some really specific how-to topic in which you are an expert. It needs to be something people are actively searching for and willing to pay money for a solution to. For instance, “How to stop sweaty palms” would probably sell a lot better than “How to become your own personal brand,” because nobody’s really searching for “how to become your own personal brand,” and there are already lots of regular books on the topic. In the past, I have purchased e-books about search engine optimization, how to make money tutoring, and some really specific bodybuilding topics. If your topic is really sexy, you could pull off being anonymous (“Blowjob secrets from a nun-turned-porn star!” Not that that example has anything to do with you, just saying that I would understand if this kind of book were anonymous, while it would be super bizarre if a book about personal branding were written by an anonymous author.)

As for services, they’re much easier.

Social media for rich people — I like it. You need to define what kind of rich people you’re talking about. Entrepreneurs? Art gallery owners?

Having sold many tech services to relatively wealthy buyers, the strategy that has always worked for me was to have two lines of attack: 1) You can spout a lot of technical-sounding terminology to impress potential clients, and 2) You follow up with, “But don’t worry I’ll take care of everything!”

I’d strongly suggest NOT charging by the hour, and instead creating packages, like:

Social Media Maintenance $299/month

Social Media Maven $600/month

Social Media “Dominate Your Market” $1,800/month

For each package, specify how many Tweets, blog posts, etc., and how many hours per week will be spent replying to messages, or searching on Twitter for people posting about certain search terms and then tweeting to them. Also, prepare fancy reports for them every week or month — make traffic graphs in Excel! And then cut and paste all the compliments they’ve gotten on Facebook and Twitter into a special report for them. I think your clients will become addicted to getting a weekly/monthly praise report. PEOPLE BUY THINGS BASED ON FEELINGS, even when they think they’re buying things based on something else.

Warehouse Clearance Sale


Overall, I think many of your buyers won’t really understand what they’re doing with social media or why they’re doing it, so they might feel uncomfortable paying hourly – after all, they don’t really get what you’re doing or how long that might take. I suspect that many will be engaging in social media (through you) because they heard they’re supposed to and they’re kind of embarrassed that they haven’t been doing it. So what they’re paying you for may not really be the service itself, so much as the feeling that, by paying a monthly bill, they are on top of something. They’re paying you so they can feel competent and avoid embarrassment.

Or, you may find that your buyers are actually really social media-savvy themselves, and expect a high level of expertise from you. In which case, now is absolutely the time to build that expertise. Social media is a great field to do that in, because there is really no such thing as, say, a masters degree in that topic (um, if there is, don’t pay money for that). With enough effort, you could become the world champion of this topic, on your own, for free. (People are often impressed when you refer them to articles in the Harvard Business Review.)

Finally, as someone who works with an assistant and a web designer, and sometimes teams of writers and editors, I can tell you that I would 1,000 times rather work with someone who says, “I’ll be responsible for this” you don’t have to worry about it” than someone who says, “I can do anything! Just tell me!” That is fucking exhausting.

As for your last point — having been on many dates as a struggling young New Yorker, yes, having some real cash in your purse (that you don’t need to pay rent) is very liberating. Don’t go anywhere where you can’t afford to say, “You’re an asshole,” throw the appropriate amount of cash on a table, and walk out. Otherwise, you end up smiling grimly at a lot of assholes until dinner is over.

Dating is definitely financially stacked against men, and many men are understandably put out by that, but a small few use this fact to try to manipulate you — they order expensive stuff on your behalf, and then start groping you or telling racist jokes or whatnot, expecting that you’ll feel too uncomfortable to leave because someone just bought you a steak even though you actually wanted the pasta. You need some money so you don’t live your life feeling beholden. (Can we put “You need some money so you don’t live your life feeling beholden” on a cross-stitch sampler, please?)

Anyway, I don’t mean to sour you on dating new people! 80% of men are more or less normal and fun to meet. Having some cash lets you waste as little time as possible with the other 20%.

Good luck!


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