10 dating tips that can help your job search

mm Russ Finkelstein

I’ve written before about the need to reach out for career advice in the same way you’d reach out for dating advice. I often compare the search for a job with the search for a relationship, because the two have so much in common. Using that framework, here are some dating tips that can help demystify the job search.

First, a few points to determine whether you are ready to start a new relationship:

Don’t jump in prematurely. We all need some time to process where things went wrong in our last romantic relationship and the same is true of work. Sometimes this means you remain in a position that is doing you no emotional harm, but gives you the space to contemplate what’s next. Other times, the pain you are feeling means you need to leave immediately and you might want to look for an interim situation.

Don’t jump because nothing better will come along. This is the most common rationale of the unhappy dater and the unhappy job seeker. You are feeling a little less desired than some friends who get heavily ‘recruited’ at a bar or via LinkedIn. Many of us have wondered why the hell they got that offer. If you feel as though you are about to say “yes” because you don’t see anything good on the horizon, take note, but try to park it, if you can.

Don’t stay because you shouldn’t expect more. In many romantic comedies there is a stock character of the bad romantic partner. S/He’s mean, indifferent, immature or boring and our hero must experience and suffer through this bad match before they can have and appreciate their true love. By this point, you are statistically likely to have had a few bad dates. In any relationship, you need to go in with your eyes open to the risks, but more importantly, remember that you deserve to be feel valued. If you feel diminished by the person you are with or the job you have, you need to begin the process of looking for something new.

What do you need to remember when you jump? If you are hurting that they never pick up the check, forget your birthday, or show affection, you know what you won’t tolerate in your next relationship. I have a friend who dated a guy who refused to share his name and age. It took her a while, but when he landed in prison and asked to move in with her she was finally able to say no. She’s a real  stickler for full names now. Hone in on the things that have frustrated you when you think back on your current and former jobs. Write them down as a reminder because you don’t want to end up at another workplace that has the same things that irked you about the last one.

Next, a few things to consider about getting out ‘in the market’:

You get out faster and further when you have help. Ask your friends if they know anybody, and ask them to ask their friends. It is socially acceptable to reach out broadly to those you know asking for people with the attributes you seek. But remember to be specific about what you want, or you might end up on a date with the world’s biggest Designing Women fan. This actually happened to me. Same deal when it comes to work. If you don’t do the work to know what you want and the words to share it with others, then nobody else stands a chance of finding you the right person.  

Get out to new places. There’s more than one way of finding people you might want to be in a relationship with. Most people seem to go through phases of enjoying and hating online dating. During those frustrated periods they will run the gamut of ways to meet people. I’m astonished by how much time people invest in seeking jobs via posting websites, tweaking their resume and cover letter, and applying. There are a robust set of ways to make much stronger and deeper connections with potential employers including professional associations, conferences, and classes. Restricting yourself to just scanning the job ads online greatly limits the possibilities.  

Finally, look closely at what’s available:

Are you Compatible? Do you want the same thing from the relationship? The proliferation of tailored dating websites means that it is actually pretty easy to know what someone is looking for. Although, to be fair, some people lie or don’t really know. However, you can still ask probing questions. When it comes to work, ask key questions to see if it fits you, such as how long the last few people have been in that position or if there is any professional trajectory for that role.

What does your gut tell you? Trust your instincts about the red flags. Everybody has issues, but when we date we tend to be on heightened alert to these things.  You might be in the work headspace that says: “anywhere is better than this,” but when you’re applying for a new position try to think ahead about how it feels to arrive at the office and quickly realize that you have just moved from one sinking ship to another. Sometimes anxiety causes us to lie to ourselves, so capture what was awful at your last job and keep this somewhere nearby as a ready reminder.

What does your vetting reveal? When you go on a date, you may spend time browsing their online profiles, meeting their friends and, if possible, see what people you know think of them before you go too far. Similarly in a job search, do you know people who currently or formerly worked there, and what they have to say? If you search for reviews on Glass Door or stories via Google, what turns up? You are always better off not being surprised.

What do your friends think?  They know you in and out of relationships and jobs. They have heard you talk about both at great length. You talk about dating and relationships with great ease, so please, please, please check in with a friend that you respect and communicate well with throughout this process.

There you have it. I hope this works to help you gain perspective on how to date better and find better job opportunities. It isn’t easy, but it need not be so hard.

Russ Finkelstein is Managing Director of ClearlyNext, a guided online career program that helps people of all backgrounds and incomes figure out what to do next. Read more >