I spent $40 and found love
An ode to Photofeeler and Wikipedia's List of Common Misconceptions. Plus: the reason I gave up my engineering salary to become a freelancer.
A piece of software that sparks joy
This is the story of the best $40 I ever spent, which immediately grew my number of matches on dating apps by 4x and, ultimately, led me to meet my future wife. Without this one investment, my life would have gone in a much worse direction, and I might still be alone today.
A few years back, I was single and focused on finding love. Though I was swiping on all the major apps, I wasn't getting a lot of matches. Impatient and dissatisfied with my results, I decided it was time to focus on the only thing in my control: my profile.
Like most men, I used the same 1-3 photos everywhere on the internet, and I wasn't particularly proud of them. Your photos are probably the most crucial part of your profile, and since I wasn't happy with the results I was getting, I decided I would need some new pictures.
Mind you, this was back in the old days when generating a hundred professional-quality images of yourself with AI was not an option. And I had an allergy to selfies. So I was going to need help from someone with a camera.
Tragically, there were no photographers in my contact book. So, with some trepidation and embarrassment, I sought out professional photographers online and prepared myself to shell out $400+ for a handful of good pictures of myself—the going rate for that service in San Francisco at the time.
It was a lot, but I reasoned that people had spent much more money on much dumber things in the pursuit of romance.
Luckily, during my search for "dating app profile photographers," I stumbled across an app called Photofeeler, which helps you get feedback on pictures.
The way it works is you upload a picture of yourself, and the app will put that picture in front of strangers in your "target demographic" (based on gender and age). Those strangers see the photo without any other information about you and then rate how smart, trustworthy, and attractive you seem on a scale of 1-4.
It sparked my curiosity. "How bad are my current pictures?" I wondered.
I decided to run a little experiment. I would put my current pictures into the tool and see how they performed. At the very least, this would allow me to establish a baseline so that whenever I got better pictures, I could quantify how much better they were.
What can I say? I'm an engineer. I love data.
In Photofeeler, you can rate other people's photos to build up "karma" points, which you cash in to have your picture shown to others. The downside is that building karma takes time, and the results come in quite slowly. On the other hand, you can pay a small fee to have your picture shown to many people very quickly. Impatient, I put in $40, uploaded my images, and waited for the results to roll in.
I quickly learned that my pictures didn't necessarily suck but that they also weren't great. Here's an actual picture from my profile at the time. I’ll warn you that, in hindsight, I have no idea why I thought this was a reasonable picture to use on a dating app. Chalk it up to being a dumb boy, I guess.
These scores are dead average, basically the epitome of "meh." Fortunately, the reviewers also left helpful comments explaining their ratings:
"Would prefer if I could see their face clearly."
"I think they seem a bit sad in this photo."
"Really cool background. Potentially decent man, but I cannot connect with you as a photo viewer on any level because a) you are looking down and b) I cannot see your eyes or expression well. Would fix that!!"
This feedback was all valid and quite well delivered. Folks tend to be very kind about the ratings they give when they know that they will also be getting ratings on their own pictures.
The takeaway was clear: I had some room to improve. The scores and ratings didn't hurt my feelings at all. They just made me excited—now I knew what my problems were! One of the frustrating things about dating apps is that you never know why someone chooses not to swipe on you. Photofeeler was giving me exactly the input I had always wished for.
The results page also contained some helpful advice relevant to my situation.
Okay, shit, so maybe hiring a photographer was not the right move.
I wondered, do I already have other, better pictures of myself—that I don't know are better because I'm a clueless boy? So I searched through my computer and phone, tracked down a few more pictures of myself, and uploaded them for ratings.
To my shock and delight, several of these photos ranked in the top 10% of all three categories! Like this one, taken in Japan within a few months of the other picture:
Naive as it may sound, this was so eye-opening to me. It actually blew my mind. How could two photos of the same person, at the same age, with the same haircut, glasses, and general style, come across so differently?
The numbers didn't lie. I submitted to the wisdom of the crowd, switched to the new photos, and immediately matches began coming in at 4x the rate they had before. I was overwhelmed by the level of interest I was getting.
Only two weeks later, I met Mallory, the love of my life, on a dating app. Almost four years later, we're still going strong!
Recently I showed her the pictures I was using before my Photofeeler experiment, and she said that if my profile contained my old photos, she probably wouldn't have matched with me.
So yeah, that $40 I put into Photofeeler was easily the best investment I’ve ever made.
Since this experiment, I've convinced at least a dozen people to use Photofeeler and used it to get feedback on photos for other contexts, like social media and business. In fact, I even used it to determine what photo I should use for this very newsletter.
I love everything about Photofeeler, including the design philosophy that it represents. It is a perfect tiny app that does one thing exceptionally well. It has zero bloat. Everything in the UI serves a purpose.
Photofeeler sets the bar by which I measure all other software tools. And I'm not just saying that because it helped me find my soulmate. 😄
A Wikipedia page everyone should read
Wikipedia's List of Common Misconceptions is precisely what it sounds like: a list of things people tend to get wrong. It is mandatory reading for all humans.
I revisit this list every few months, and each time I discover something new that I was wrong about. It is a never-ending source of facts that you can introduce with the phrase "Well, actually..."
This list is so great that I gave a short presentation on it at a PowerPoint Party. The article stands on its own, but if you'd like a guided tour with some fun visuals, here are those slides.
This slide is my personal favorite. It turns out that mice don’t actually like cheese. They actually prefer sweet foods and will only eat cheese if there’s nothing better available.
A prompt for self-reflection
In Ignore Everybody, cartoonist Hugh MacLeod writes, "The most important thing a creative person can learn professionally is where to draw the red line that separates what you are willing to do from what you are not."
How do you know what your line is? He describes it like this: "What crap you are willing to take, and what crap you're not. What you are willing to relinquish control over, and what you aren't. What price you are willing to pay, and what price you aren't."
Establishing this line can teach you who you are and what you value.
I drew this line almost a year ago when I left my salaried tech job to become a freelance software consultant.
Switching to freelancing is not a standard career move. Many of my friends are engineers, and the vast majority have never even considered working on an hourly, contract basis.
Why would they? Being employed by a tech company provides tons of benefits. Things like:
A steady paycheck
Unlimited PTO and sick days
Excellent health, dental, and vision insurance, often for less than $100 per month in total
Life, disability, worker's compensation, and AD&D insurance, without any underwriting process—and often for free
Yearly compensation increases and generous equity grants
401k matching
~$2k yearly to spend on professional development
Compare that to freelancing:
No steady paycheck
Your income will go up and down by thousands of dollars per month and then drop to zero whenever a contract ends. Good luck with your financial planning.
No PTO
If you ever want to take a vacation or a sick day, go ahead, but you will make $0 until you get back to work.
Insurance? Lol.
Now it's on you to obtain health, dental, and vision insurance. Expect to pay hundreds per month for significantly worse coverage.
Want life or disability insurance? Get ready for a lengthy underwriting process, wherein you must spend hours answering highly personal questions about your medical history and, in some cases, give the insurance company your blood so they can more accurately estimate when you're going to die.
I went through that process myself this year. It took 7+ months to get a plan which costs several thousand dollars annually, compared to the $0 that I paid for better coverage at my last tech job.
You will get no equity, no 401k matching, and no professional development budget.
On top of that, you must now pay taxes four times per year, carry various forms of business insurance, build a brand online, constantly network to find your next contract...the list goes on!
Yes, I'm complaining, but file everything I just listed under "crap I'm willing to deal with."
Sure my income is variable, but I like it that way! It feels more swashbuckling and keeps me from getting too comfortable. Steady paychecks give a false sense of security, lulling people into complacency until they suddenly get laid off—like we see happening all across the tech industry.
Yes, there's a lot of administrative overhead, but with a good CPA, a few self-employed friends to ask for advice, and a copy of Working For Yourself, it's possible to learn everything you need to get started. Heck, you may even find that figuring out how to navigate these systems can be kind of fun.
Every decision we make in life has tradeoffs. The challenge is finding which tradeoffs are worth it to you.
As Mark Manson puts it in The Most Important Question of Your Life, "What we get out of life is not determined by the good feelings we desire, but by what bad feelings we're willing and able to sustain to get us to those good feelings."
So ask yourself, what suffering are you willing to endure?
With a smile on my face, I will endure the administrative headaches, anxieties, and cash-flow woes of the self-employed. However, here's what I'm not willing to tolerate:
Letting a committee of managers decide if I'm worthy of a promotion based on some contrived "career ladder"
Waiting a year for an annual compensation review if I know my pay is below the going market rate for my skills
Employers dictating how and when I do my work
Leaving my fate in the hands of some VP who can unilaterally decide to move me to a new team I have no interest in
Corporate politics
Endless all-hands meetings
Employee agreements that limit what I'm able to do in my free time
The Golden Handcuffs: stock vesting schedules that manipulate you into staying in a job for longer than you would otherwise
That's my bright red line. What's yours?