5 Ways a Career Hunt is like Dating

61 – Five Ways a Career Hunt is Like Dating


In this episode, I’m going to share with you the five ways I’ve found that a career hunt is like dating. It’s time to start something new and fresh, to put yourself out on the market, and to try to attract something that’s a better fit for you. It can be both exciting and terrifying.

Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.

Five Ways a Career Hunt is Like Dating

Hey there. Welcome to The Teacher Career Coach Podcast. I’m your host Daphne Gomez. So you are stuck in a rut, and you know that something is not working in your current situation, and you just don’t know what to do.

It’s time to start something new and fresh to put yourself out on the market and to attract something that’s a better fit for you. This huge change in your life’s direction is exciting and terrifying all at the same time.

While this may sound like I’m describing getting back into the dating scene, I have actually realized over the years while helping thousands of teachers transition into their new careers, just how similar dating and career hunting can be.

In this episode of The Teacher Career Coach Podcast, I’m going to share five ways that your job search is just like dating. I think that number five is one of the most important ones, so please make sure you stay until the very end of this episode.

1. How Time Affects Your Career Hunt

The very first reason that I want to dive into is, the longer that you’ve been in a relationship or a job, the harder the adjustment is going to be. For many of us, teaching was like a marriage. Even if you were a teacher for a short amount of time, you went into it expecting it to be your forever career. So having whiplash from an immediate change in direction or realizing your relationship is toxic is expected.

It’s okay to feel like you’re a little bit in shock during this phase. I’m not saying that adjusting to new roles or learning new skills is going to be easier for those newer teachers. That’s not it. Every single one of you listening, from teachers with two years experience to 20 years experience, you’re going to have your own unique strengths that you are bringing to the table. You’re special, you are talented, you’re adaptable, and you’re stronger than you realize.

If you’ve been teaching for many years…

But for those of you who have been in the industry longer, in addition to a few different challenges you’ll need to overcome, it may take you a little bit longer to pick your new path. I once heard someone describe it like the Titanic, which had been moving in one direction with all of its weight and force for quite some time. As we all know, ships don’t really turn fast. If you’ve been going in one direction for a while it may take more time and patience for you to be able to completely turn around.

This is the same with those who are in relationships. If you are breaking up with your boyfriend after two months it’s going to feel a lot different than if it’s a marriage that’s broken after 15 years. You have to know where you’re going and just have patience in the process of getting there.

Giving Yourself Grace

It’s so easy during this process to think that something’s wrong with us, to blame ourselves, and to look ourselves in the mirror with disgust and just ask, “Why can’t I just get over it?” But during this time, no matter how long you’ve been in the classroom, if you feel hurt right now, give yourself some grace and expect that it’s going to take some time to heal.

While I have heard many stories of luck in both love and career, often you’re going to have to be clear on what you actually want and start looking for it. So you need to know what you’re looking for, and this process alone is going to take some soul searching to figure out.

Determining Your Career Path

You know, “I want any career out of teaching,” is something I hear so often. It’s a start, but it’s so vague that no one can really help you. It’s like saying, “I’m open to dating anyone but Steve.” If you are still struggling with this phase, I urge you to take my free career quiz, or start to really pinpoint one or two direct roles. Because if you are able to say something like, “I’d like to be in a role where I train adults or create the training resources for adults,” that’s so much further of a start. You can start refining it, having more specifics, and even add flexibility as you see fit.

If you’re really picky, it’s going to take you a little bit longer to find a new partner and a new role, and that is totally okay. This is not a decision that anyone should make for you. And this is not something that should be made quickly and without a lot of thought.

Things you should start to think about:

  • How far the commute will be
  • What’s your firm starting salary?
  • Make sure during this phase that you don’t forget to factor in things like paid time off
  • matching 401(k)
  • working a true 40-hour work week
  • potential commissions and other benefits that you wouldn’t have with your teaching salary

But make sure you know this upfront.

Deal Breakers in Your Career Hunt & Dating

I want to share a little story about Jonathan and I. We actually first started dating on OkCupid. I remember seeing his profile, and on top of being handsome I immediately noticed we had so many similar interests. We had similar music tastes. He liked many of the same films as me. We had similar political beliefs, loved hiking, and immediately I was crushing on him hard after he sent me some videos of him singing songs to our dog Charles.

Our commute was two to three hours to actually see each other. We were dating casually long distance. I was open to dating someone long distance, and if distance was a deal breaker for me, I would have never matched with him. We actually casually dated for about eight months before I moved near him, and then we officially started dating then.

Other people dating may have wanted something serious more immediately. Someone local to spend their every moment with. But this actually worked best for both of us where we were at in those moments of our lives. Everyone has firm negotiables, but it’s okay if yours are different than other people’s. Just make sure to evaluate yours to make sure they’re not blocking you from opportunities that may be good for you just because they’re different or you’re afraid of change.

2. Presenting Yourself While Dating & on a Career Hunt

The second way I found that a career hunt is like dating is all about how you present yourself. You have to learn to talk about yourself and present yourself in a manner that best attracts the results that you crave. So if you’re seeking a job opportunity, you don’t want to come across desperate or like someone who’s dwelling on the past, in the same way you wouldn’t want to on a first date. There’s going to be a difference between being interested in a role and excited and coming across desperate.

So going back to my OkCupid profile. I didn’t mention my past toxic relationships, but oh do I have stories! You know, we all have pasts. We all have hurts. But we have to be selective on how we address them. That means I would not recommend using LinkedIn to air your grievances about the teaching profession any more than I would advise you to use your OkCupid profile to rant about how Steve didn’t tell you he loved you as much as you deserved. Or how he never wanted to have children even though he knew how important it was to you, or how you have suspicions that he may have not been faithful.

Taking About Past Relationships & Careers

Even though these are perfectly human emotions to feel, and I totally have your back on feeling them, there is a time and a place. Once you get to know that person better, you talk great in detail about your past relationships. What made them fail. What you learned from them, and how you grow. But any dramatic mention of an ex too soon can leave those that you’re talking to curious if you’re still dwelling on it, if haven’t gotten over it, or if truly you’re the person who’s dramatic or hard to get along with.

I recently saw a copy and pasted message that a teacher had written for other teachers on how to address why they were leaving the classroom for interviews. It was written by someone who was really articulate, but there were many parts of this resource that jumped out to me.

Phrases like, “You couldn’t thrive while being micromanaged,” that so many hiring managers may view as red flags. While I do not doubt for a second that these are true for many of you during an interview, it’s just not the place to come across angry, or defensive, or point fingers. So if you haven’t listened to Episode 34 of the podcast, All About Interviewing Outside of the Classroom, I do recommend jumping over to that episode after finishing this one as well.

5 Ways a Career Hunt is like Dating

3. Branching Out & Networking

Number three, you don’t want your only networking to be with others in the same situation. You know, this isn’t a game of The Bachelor. This is such a common thing that I see teachers do, especially on LinkedIn. They add hundreds of other teachers who are all interested in potentially the same roles as them.

I am not putting down this strategy because I love the fact that you are seeking a community. I believe having a community to learn and grow with is so strong, especially for motivation. But real talk, you don’t want to only be in the exact same spaces as everyone else.

You want to start branching out to areas where only you have ins to the company, to people only you have connections with. So please make sure that this isn’t your only networking strategy.

Where to Ask Questions About Your Career Hunt

And I’ve always given this advice, to not ask things on LinkedIn that are easily Googleable. In the same way that you wouldn’t want to be asking for first date tips publicly where you’re searching for your matches.

For those of you who are in the private Teacher Career Coach Course Community, I recommend you put questions there for other teachers. As opposed to something that may pop up on your LinkedIn profile for a hiring manager to see.

4. Not All Advice is Created Equally: In Dating & on a Career Hunt

Number four, other people are going to have a lot of advice on what you should or shouldn’t do. And not all advice is created equally. If when I was single my mom suggested I date someone, I would know matter of factly that the person was the exact opposite of who I would be interested in.

Or there were coworkers of mine who would try and get me to date the rich guy who after I met had the personality of someone that you would only be able to describe as wealthy. But they insisted that that was a quality I should be looking for. But then at the same time, Jonathan and I received so much great advice for keeping our marriage strong from some of the same loved ones on our wedding day. My point is that some advice just needs to be taken with a grain of salt depending on what you need support with.

Who You Love & What You Do

Maybe your loved ones don’t accept who you choose to love or what you want to do, and continue to push you in a different direction. One that they wanted for you. Many are going to try and fit you into a box that you just might not fit into. And some may tell you that you can’t quit teaching at all, just because you’re a great teacher. Or other former teachers will tell you that you should go into instructional design or corporate training because that’s what they fell into.

But if it doesn’t click with you in the same way, you can continue to look until you figure out what does. A job title does not define you or make you who you are. It does not matter what anyone else thinks of your new job title. It only matters what your needs are, and if they are met, and that you are happy, period. Who you love or what you do is not anyone else’s business but yours.

Where is Your Career & Dating Advice Coming From?

You may also need to evaluate who you’re actually taking advice from. Because while you may be getting great advice on your wedding day, there’s also going to be a lot of bad advice out there for when times get tough.

Going back to that interview advice that was floating around. I am 99% certain that it was not written by someone who actually had experience in interviewing others. I believe that it was just written by someone trying to help others. And creating resources that they think would be helpful.

You need to figure out who’s who when you’re listening to outside voices that are guiding you. There are people who are going to be giving career coaching advice, who are not qualified to give career advice. In the same way, you may be getting relationship advice from those who aren’t necessarily qualified.

Seeking Expert Advice

What I mean is, if you are in a crisis, you would probably need to seek expert advice like certified couples therapy before listening to your friend who just has a lot of strong opinions or a stranger on the internet who just says that they’ve been in a great relationship for three months so they know how to make it work.

Those who are truly qualified to give interview or resume advice in times of crisis have held experienced positions in either recruiting or human resources.

So a customer success manager, for example, is not going to have the same level of experience as someone who actually sources the resumes to select the top candidates for positions. So if you’re looking for qualified advice on best practices, I recommend going back to Episode 29 of The Teacher Career Coach Podcast, where we interview our team’s resume writer.

5. Rejection Hurts in Dating & on Your Career Hunt

The very last way that a career hunt is like dating is one of the most important. It is that understanding the fact that no matter what, rejection is going to hurt. No matter how much you think you’re prepared for it, this is going to sting. And when you decide to put yourself out there again, you are most likely going to face rejection. Unless you are one of the very few lucky ones who gets the very first job they interview for.

Some job rejections hurt you far more than you thought they were. And some days it may hit you much harder than the week before. And your self-esteem is going to take a blow. You’ll start to think that it’s you, that you’ll truly never find the right fit. But that is not true. Every single person goes through these phases of imposter syndrome.

Moving Forward Through Rejection

I want you to keep searching, and growing, and learning. And know in your heart that the right match is going to come along for you. Every time you get a rejection that hurts, give yourself a treat for being brave and facing rejection.

So get a rejection, watch a movie that just came out. Get a rejection, go on a walk in the garden or something that brings you joy. Get a rejection, paint your nails. They’re very small things. But just knowing that you’re getting stronger and that every time you get rejected, you are growing.

Your Own Unique Timeline

Realize that whoever rejected you, that person is not your person. Or that role is not your role. But the best part is, when you find the right fit, you’re going to feel more like yourself than you’ve ever felt in your entire life. And you’re going to realize all of those rejections were directing you to exactly where you needed to be in your life. I know that this is so hard to see and believe when you are in the middle of it. But I promise you that it will happen for you too.

Unfortunately, there is no guaranteed timeline of when it would happen. Everybody is on their own unique journey. But it will happen for you as long as you don’t give up. The only true way to fail here is just to stop altogether.

If you find The Teacher Career Coach Podcast helpful and want to help support us, please post about it on Instagram or Facebook. And help us just spread word that this free support exists. Every day we receive DMs from new teachers who are grateful that they just found this page and community. Your support helps the community just grow so strong.

Thank you so much for listening to this episode and I’ll see you on the next episode of The Teacher Career Coach Podcast.

Important Links

Mentioned in this podcast:

Related Blog: Career Transition Timeline for Teachers

Find out about The Teacher Career Coach Course

If you’re thinking of leaving teaching…

If you’re just beginning to think about leaving teaching, brainstorming other options is a great place to start your career hunt. But if you’re like many others, teaching was your only plan – there never was a Plan B. You might feel at a loss when it comes to figuring out what alternatives are out there.

Start with our free quiz, below, to get alternative job options for careers that really do hire teachers!

What career outside the classroom is right for YOU? Free Quiz

Next Steps for Your Career Hunt

If you’ve already taken our quiz, it may be time for the next steps. I want to help you get some clarity in the options available to you. To know EXACTLY what you need to do (and not do) in order to get your foot in the door. This knowledge may help quell some of the anxiety you feel about the big changes that come with a new job.

One of the biggest mistakes that I see teachers make is that they try to navigate this process alone. Often, they put off “researching” until the very last minute. Which sets them up for a very stressful application season – trying to juggle teaching, figuring out a resume, researching jobs, and hoping to nail down some interviews before signing next year’s contract.

You don’t have to do this on your own.

If you are considering a career change from teaching, I have a resource that can help you today. With the help of an HR expert with over 10 years of experience, I’ve created a guide to support you in the early stages of your transition out of the classroom.

In the Career Transition Guide, I’ll walk you through the factors to consider and answer those first-step planning questions including:

Career Transition Guide
  • A compiled list of over 40 careers that teachers can transition into
  • An overview of how to read job descriptions
  • How to evaluate the risk of leaving a full-time teaching job for the unknown
  • Example translations from classroom-to-corporate resumes
  • A checklist of everything you’ll need to do for your career transition (so you know you aren’t missing anything!)
  • and more…

Take the first steps on your path to a new career now for only $19 $9!


or click here to learn more

Step out of the classroom and into a new career, The Teacher Career Coach Course