10 Ways to Make a Job Search A Little Less Painful


Let’s not sugarcoat this; searching for a job can really suck. And the more you need a new job, the suckier it will probably feel. Like life-sucking. See, no lollipops and roses here. I’ve looked for a lot of jobs, both for myself and for others. And there have been extended periods of painfulness. But I’ve also uncovered some ways to make it not only less crappy, but actually fun and an experience that results in both a great new job and some meaningful connections along the way.

So take a deep breath, and let’s focus on some ways to 1- make it go a bit faster, and 2- make it suck a little less, and 3- get you some awesome results. Sound good?

1. Brace yourself for the journey. It’s most likely going to take you some time; be ok with that. Maybe you’ll be the anomaly that falls in love and gets the first job you find, but please don’t put your eggs in that basket.  

2. Stop trolling Indeed.com. Or all those other job sites. They are a demotivating waste of your time.  How many people do you know that actually got jobs that way? Sure, it can be useful to get a better understanding of the jobs that are out there, but most of the time, it leaves you feeling empty.  

3. Don’t leave before you leave. If you have a job, stick with it and go to work each day like you’ll be at this job for the rest of your life. There’s a tendency - I know because I’ve been there - to decide you’re going to get a new job and then completely check out at your current job. Besides the fact that that could lead to you not having a job anymore, it leaves you demoralized and puts you in a position of weakness. You want to come at your job search from a position of strength. Which leads me to my next point…

4. Come at the job search from a position of strength. Potential employers and networking connections can smell desperation from a mile away. No one wants to hear you bad mouth your current employer or sound like you’re disengaged in what you do everyday. It also hurts your negotiating position if a future employer thinks you’re desperate for the job. And it hurts you because you’ll end up compromising and taking a job that isn’t good for you in the long run.

5. Get busy. For those of you searching for a job without a job, that’s totally normal. Maybe you lost your job or quit - it doesn’t really matter - you have to figure out what you’re going to do during your search. While searching for a job can be a full-time job, I don’t recommend it. It takes you out of your position of strength and, honestly, it can be kind of depressing. So try to find something part-time, even if it’s not something you want to be doing for the long haul. Even better if it can fit into your story (see below). For example, maybe you’re looking for a job in corporate sales. Working at a clothing store is not probably the most appealing to you, but it does fit into your story of connecting with people, selling a good, and by the way, there’s a little bit of cash involved. If you don’t want to get a part-time job, think about volunteering or a consulting gig (you can call it part time even if it’s only a few hours a week) or starting your own blog. Do something that enhances your story and keeps you from watching Netflix.

6. Figure out what you want. Be prepared to spend some time here. You’ll want to start by looking inward; this is a good place to work with a coach (I know a pretty cool one…). Start exploring what your values are, what really matters to you, and what you find fulfilling. Being honest and authentic about this is hard work and not something to take lightly. For example, maybe you’ve been on the accounting path for a long time. You went to business school, got your CPA, and have been climbing the ladder in this field. But if this isn’t where your passion is, you need to stop pushing it under the rug. It can be scary and easier to ignore than confront head on, but I promise, it’s necessary. Life is too short to hate what you do all day.

7. Write your story. Obviously you have to put your resume and cover letter together. But once you have a clearer sense of what you want, you need to write your story. This is the story of what you’ve done, why you’ve done it, and where you're going next.  It doesn’t have to be beautifully written, just get something down on paper. You’ll refine it as you speak it, but you need something to start from and that you can come back to. Write it as if you were speaking. Let me be clear: this is not you reading off your resume; this is an entertaining view on the path you’ve taken; like you’re telling a new friend. Get clear on how and why you’ve chosen this path. Be proud of your story and get ready to share it.

8. Make a list of everyone you know in Excel. Seriously, everyone. Here are some places to get started: all of your past jobs; your family friends; your family friends’ friends, your friends from high school/college/grad school; neighbors; connections on social media… It doesn’t matter what they do, just put them down on the list. Then highlight all of the people you’re willing to reach out to. Go through it again and highlight a few of the people you said you weren’t willing to reach out to. Just a few.

9. Write some templated emails. These are short emails that you can personalize when you start reaching out to your list. Be clear, be direct, and put in a call to action. Here’s an example:

Dear XXXX,

[insert personalized greeting: “It was great to see you at Jenny’s Christmas party a few months ago.”]

As you may know, I’ve been at XYZ company for two years, and while I’m still enjoying my work, I’ve started to wonder about a career in [insert career path]. I’m in the very early, exploratory phases and would love to grab a cup of coffee and pick your brain about [insert topic].

Would you have any time to catch up in the next two weeks?


Your name

These emails will look different depending on if you currently have a job or not; if you’re planning to switch jobs vs. careers; if the person you’re reaching out to has connections in your industry vs. connections to someone who may have connections to someone else; etc. You’ll probably want a few different templates.

10. Hit send. It's terrifying to send out this kind of an email (believe me, I know).  Set a goal for how many you want to send each day (maybe 10?) and get sending. Be careful that you get everything customized correctly; it’s embarrassing to reach out to Joe and write, “I loved meeting your husband,” when you know Joe through his lovely wife, Mary. Also, make sure you use your excel document to track everything. Note when you reach out, responses you get, connections someone makes for you, thank you notes sent (make sure you always do that!), etc. When you get your job, you’re going to want to follow up with everyone who helped you get there.

You’ll notice that none of these steps fit the typical job search path of:

  • Update your resume

  • Write your cover letter

  • Send out applications

Those are important steps, but I highly recommend that you start your search from a different place. Don’t bring your resume to these coffee dates, and don’t ask for a job.  

This is a time to start getting the word out on the street that you’re looking, help people help you by being clear on your story and what you’re looking for, and to build connections and authentic relationships. The ask at the end of your coffee date is for more people you should talk to and to be able to stay in touch with this person moving forward.  Ideas about where to apply will come throughout the conversation, but building your network is the most valuable thing you can do. The more people who want to help you - and know how to - the better chance you’ll have and the more enjoyable the process will be.  And stay in touch with all of your connections - keep them updated on your progress and how they’ve helped you. 

Another bonus of this approach: you’ll be creating a beautiful network that you can tap to help all of the people who are helping you when they need it one day.  Remember, what goes around comes around.

So, get out there and begin your work.  Let me know how much it sucks… or doesn’t.