I've been a job seeker and a hiring manager who recruits for more than a decade each—I have been on both sides of it. I am also a former single person who once sought a relationship. It wasn't until I gained experience in the recruiting and hiring process that I realized both are the same emotional journeys and a similar goal of full-time commitment (and side hustles if you swing that way). Both experiences are emotionally draining.

As a person who is passionate about helping people thrive in their careers and matchmake my single friends¹, let’s explore the common journeys, what emotional arcs you may endure, and a few tips and tricks to help you along the way to get what you’re looking for.

The shared journey

It’s astonishing how similar a person seeking a job encounters paths identical to dating. Different companies interview differently and I’ll generalize the phases for discussion.

1. Holla—slide into DMs (Inquiry)
This is where you're a hatchling turtle making it to sea—the odds aren't great and you should know it. At this stage, you'll get a response quickly (or not at all) if they’re interested. It's a volume game at this stage.

2. Swipe right (Initial call)
Things look good at an initial glance and now it’s time to get to know each other a bit more. The conversation is low-pressure to get to know a bit about one another. This is where a job seeker can share their experience and what they’re optimizing for the longer term. If there is enough signal amongst both parties, it goes to a formal loop.

3. Impress your date (Interview loops)
The vibes are feeling good. You had the initial conversation and went on a few dates. Now it's time to get validation from the squad. The dates might turn into brunch to meet their friends. At this stage, it's about winning over the friends and getting positive signals from a 360 perspective. The friends will check the person you're dating on their biases and hold a high standard for them. If you make it past this stage, it's looking good.

4. Locking it down (Offer/references)
In Saved By the Bell, this was called Going Steady—the phase where you Define The Relationship (DTR) and things are getting serious. Congrats on making it this far! However, it’s not over yet and this is the phase where you’ll be tested the most: your willingness to commit and take the leap of faith. The casual dating has now turned into contemplating something dedicated and full-time. It's important to be honest with yourself in this commitment for the long term. What is worse than not getting the role is taking a role that's not a good fit and realizing it a few months in.

Insights

It's no wonder the emotional arcs feel the same. Both start as low-pressure scenarios that can lead to something magical...or tremendous heartbreak. The odds aren't in people's favor as the latter happens way more than the former.

It's a numbers game (to a certain point)

Dating and job seeking are a numbers game. If you don't put yourself out there, nothing will happen. As the old saying goes, "You miss 100% of the shots you don't take,” so shoot your shot. However, this logic is dangerous if you follow it blindly. It can be normal to get rejected a lot, but if you're getting hundreds of rejections without changing your strategy or adjusting your expectations, you’ll land on similar results.

After a certain point, reflect on why people are saying "no". Nobody is going to give you specific feedback, and this is where your EQ kicks in. Assess why people aren't saying yes. Are they not attracted to you? Perhaps the intros aren't effective. Maybe you're not asking enough about them and having a dialog. Be reflective and make adjustments.

Adjust expectations and the target pool

Unless you're optimizing for remote, the environment and target pool will be a huge factor. According to estimates by the U.S. Census Bureau, There are 800,000 to 1,000,000 single women and 700,000 to 900,000 single men in New York City. Let's assume you're a woman looking for a man, the odds of looking for a man who is looking for a long-term relationship are not great. In contrast, there are lots of dudes in San Francisco.

Consider the environment and criteria for what you're seeking. There is a likelihood that either dialing it back or refining your criteria and where to find it improves results. Perhaps you're seeking that six-foot-plus guy and the perfect one is a measly 5'10". It might also mean you need to change that filter from "a human with a pulse" and be more specific about who might be compatible with you.

Focus on yourself

Focusing on yourself is the advice that sounds terrible but in reality, it's the most important. Years ago during a coffee chat with a friend, he suggested I work on myself, saying that if I did it'd increase the contrast of what I was seeking—becoming a beacon. My friend was absolutely right. In 2018, I focused on myself—worked out, put myself out there, and pursued the best version of myself.

The best inquiries came when I wasn't looking for one. After spending time adding quality work to my portfolio, improving on my craft, and shipping impactful projects, it became more of a signal than applying for roles. The one might show up when you're not looking and you are the one who attracts them.

Tips and tricks

Boundaries and consent

In any relationship, having clear boundaries and consent is the most important rule. If you encroach on this, trust is completely broken. Be clear on the boundaries in which you'd like to be communicated and what you're comfortable with. For example, my phone is my private channel of communication. There are a few recruiters I know closely on a text message basis. However, when an external recruiter's first contact is texting me or calling me on my cell phone, it's a huge turnoff. I make my LinkedIn and email public for the reason to reach out there.

Clear communication and feedback

Avoid ghosting people (unless there is a toxic circumstance). Being honest and giving feedback can go a long way. For many people, they simply want to know where they stand. It's okay to say, "This role isn't exactly what I'm looking for" or "We're looking for a candidate with a bit more experience." It's okay to leave it high level. This doesn't need to turn into a court case; share the decision so people know whether there is anything there.

Don't get desperate (especially if you are)

There is nothing more important than keeping desperation at bay. Keep your composure and do not show desperation. When you do, it makes you appear unattractive to everyone. Recruiters and potential partners can smell if you're desperate.

Don't text her repeatedly wondering why she hasn't responded. Give people space for reflection and the next steps (if there are any). Avoid being the person who applies for every role, especially where there is a clear gap in compatibility. Applying for Apple's Human Interface Group at entry level is like asking out Dua Lipa—in your dreams.

I've personally been there. During the recession of the 2000s, there was a point where I started accepting defeat that I couldn't land a design job. It was to the point that I pondered getting a job to pay the bills. Despite planning for the worst, I hoped for the best in every interview so that I could be the person they were looking for.

You only need one to work out

In dating and job seeking, the odds are higher for getting rejected. Many experienced falling into the pit of despair and giving up on finding love. When you talk to people who've found their personal or career lobster, they'll say it was worth the pain and heartache. You only need to land the one. Whether it’s a DocuSign letter or that wedding ring, I wish you the best of luck!

Hyperlinks + notes

A collection of references for this post, updates, and weekly reads.

• Founder Mode by Paul Graham

• Low fidelity design is higher up the value chain by Pavel Samsonov

I made previous popular posts available for free on my blog:

• Bring Your Own Abstraction (BYOA)

• Choosing a company

• Your career hype doc

• Tech is going through a Factory Reset moment

• The role of taste (and what it means)