How becoming my own boss changed my dating life for the better
It’s late on a Sunday night and I’m sitting in a recliner chair with my laptop. A guy named Jacob is on the floor beside me, down on one knee, asking if he can be the only man in my life.
Before you bust out the champagne for congratulation toasts, I’ll have you know that I declined his offer. But Jacob wasn’t asking me to marry him. He was asking if I’d come work for his digital marketing agency full-time instead of freelancing. And he wasn’t the first guy to ask me the very same thing that week. So, why did I say no? After all, I’d be getting a 100% pay increase, I’d have way more stability (in my finances and in my life), and I could finally succinctly answer the ever-dreaded question of, “So, what do you do?”
I said no because I’m not ready to settle just yet—whether it be in my professional life or in my romantic endeavors.
In fact, going freelance one year ago and becoming my own boss completely changed the way I view romantic relationships and dating. Not because I added “CEO” to my Tinder bio and started racking up matches, but because I stopped settling for what I thought I was supposed to want, and started becoming more comfortable with what I actually wanted. I also accepted (or, more realistically, am continually working to accept) that finding “true love” and/or your “dream job” is not a race to the finish. It’s more about enjoying the ride.
Here’s how becoming my own boss made me see dating in a new (and much more flattering) light, and how you can do it too:
1My standards went way up.
When you graduate college, chances are you accept the first job offer you receive (or, if you’re lucky, you accept one of many job offers that you receive). You probably don’t say, “Gee, this benefits package looks great, but I don’t think this is my dream job. I’m going to keep applying to other jobs and see if I find something better.”
Of course, this is because you have bills to pay. It’s not financially responsible to keep dawdling around in hopes of finding a “dream job”—especially when you’re a recent graduate who might not have a ton of experience to offer a company.
Similarly, when I first went freelance, I accepted nearly any gig I could find. That included writing SEO copy for a VR porn blog at a measly six cents per word—no regrets, tbh, that job was fun—but as I progressed in my freelance career and took on more regular projects, I had to learn to start saying no. This was a bit of a crazy concept to me; I still wasn’t making a lot of money so it seemed silly to refuse extra income. But I quickly realized that my sanity, not to mention the quality of my other work, depended on me putting my foot down instead of overworking myself.
In a weird way, upping my freelancer rates and learning to say no has mirrored the progression of my dating life. When I started using dating apps back in 2014, I definitely had standards when swiping—but they weren’t really my standards. Instead of only swiping right on guys that interested me, I swiped right on guys that would interest my friends, or my parents, or society as a whole. My inner monologue would say, “Hmm..Ben from Long Island isn’t really my type, but he’s conventionally attractive and has the kind of job my parents would be happy about. Maybe I’ll give it a shot.”
This resulted in me going on a ton of first dates and hardly any second dates. I wasn’t even excited for 99% of those first dates since I knew I wasn’t into the person. I was lonely, wanted attention, and had a bit of a void to fill (c’mon, don’t act like you don’t know the void). Learning to trust my gut and say no immediately, rather than “Well, I’m free and could use the extra money [or attention, if it’s a date]” is a big reason for why my first dates have improved.
2If plans aren’t made in advance, they’re not happening.
Being a freelancer has made me insanely organized. I almost want to say it’s made me pseudo-type A. If a dude asks me on a date nowadays, I want to know every single detail beforehand. That means I’m asking where we’re going, what we’re doing, and even where the hell I’m supposed to park—and this is all probably two weeks in advance.
Yes, this makes me sound very intense, but it saves me from wasting my time on a date I know I’m not going to enjoy. (It saves the guy’s time and money, too.) It also stops me from being available for a guy who doesn’t value my time. You know the type: the guy who always makes tentative plans (i.e: “I’m around this weekend but I wanna see you 😉”), and never follows through until the last minute.
I never want to be the girl who is waiting around for some guy to hit her with the “come through.” It has become a lot easier to avoid that now that I charge hourly for my time in my work life. Sure, I do run the risk of freaking a guy out by peppering him with questions pre-date, but do I really want to go out with a guy who gets freaked out by that? Probably not!
3 I “tested” potential dates the way I would test potential hires.
As I started taking on more consulting work for a digital marketing agency, my “boss” gave me the opportunity to hire people. I’d never done that before, and while I definitely made some mistakes in the beginning, I also learned how to spot red flags early on. Specifically, I learned to read prospective employees’ responses to certain events.
To my horror, I realized I was sort of doing the same thing with a guy who was trying to take me out. Essentially, I met a friend of a friend at a bar, we exchanged numbers, and he texted me asking if I wanted to get ice cream with him that weekend. I immediately explained that I can’t get ice cream because I’m lactose intolerant, but that I’d be down for deep fried Oreos (see #4 on this list). When he responded that he wasn’t sure where to get deep fried Oreos, then later texted me with a couple of places to snag them, I was impressed.
But then I realized, even if it was completely unintentional, I was basically testing him. I could have easily just told him where we could get the treats, but I didn’t. If he couldn’t take initiative and figure it out, I figured that I didn’t really want to go out with him. Yes, this newly formed habit could definitely be considered a bad thing, but as someone who has previously fallen into relationships with guys who refused to take initiative, I know that I need a partner who is assertive and resourceful. As long as I’m not intentionally “testing” someone, then I don’t think it’s the worst thing in the world for my sanity.
4I became less afraid to ask for what I really wanted.
Just like I no longer worry about my incessant questioning, I’m also way more likely to tell guys how I really feel about something (particularly if I’m not into something).
A common theme in career and relationship advice (especially for women) is that you have to suffer before you reap the reward. In the workplace, this comes from CEOs who says stuff like, “I remember eating ramen noodles for a year straight when I started my company, and now I’m a billionaire.” Or the manager who says, “I worked as an unpaid intern, stayed late, and did all the bullshit work, and that’s how I made it to where I am now.” In relationships, it’s women who say, “I remember when I first started seeing Adrien, he didn’t even have a bed frame,” or “Remember when Brad used to drive me crazy by not texting me back for weeks at a time? But look at us now! So happy!”
I’m not saying that the aforementioned managers and women are liars, but I am saying that life is short and I don’t want to have to suffer in a job or a relationship that doesn’t treat me right just because it might be “worth it” later. Hard work is important and necessary for progress at work and in love—but not at the expense of my wellbeing and sanity.
As a freelancer, if I’m considered for a gig that is trying to lowball me, I’ve learned to ask for the rate I desire. If they’re not budging and I’m not super passionate about the project, I walk away. There will always be more work. In relationships (and even in casual dating), I’ve tried to adopt the same mentality. It’s not easy, but if something isn’t making me happy or isn’t cool with me, I’ll bring it up immediately. If the guy brushes me off, I walk away. There will always be more men (and if not, that’s honestly okay, too).
5I accepted that, at the end of the day, if you want something right, you have to do it yourself.
When I started hiring and managing people, I realized that it’s often easier to simply do things yourself—especially if, like me, you’re incredibly impatient.
In previous relationships, I was extremely guilty of adopting what my dad has dubbed “learned helplessness.” Instead of doing something I’m completely capable of, I’d rely on someone else to do it for me because I knew they would. All it did was leave me annoyed with my significant other for not doing things exactly as I wanted them done. Since working for myself, I’ve realized that, while having someone help you out (or more realistically, do the shit you don’t feel like doing) sounds nice, sometimes it results in an even bigger headache.
Of course, it’s great for a significant other to help me out with certain things, but solely depending on a romantic partner has always led me to disappointment and frustration. I prefer to depend on myself, not to mention my friends and family.
And if I do eventually find someone who I know I can always depend on? Well, then I don’t think it’ll feel like settling, do you?