Tell Me About Yourself: Lessons from the Job Search Trenches


Sydney Hodgson | @SydneyLHodgson

Looking for jobs is literally the worst. And I say that with recognition “literally” is also the most annoying word a person can use. But that’s how I feel.

Since finishing college, I have been on a continuous hunt for jobs. The hours of 8 to 5 (on a good day) have been committed to various employers, but after hours my mind is continuously scanning job boards and imagining days spent in a different office. Blame it on the restless nature of my millennial generation or the fact I have moved from the unstable field of politics to the ever changing space of startups, but for whatever reason, I am never not looking for jobs. A blurry, amorphous vision of my ideal occupation seems to prevent any contentment with my existing job.

The job search is an all-consuming soul suck and I always end up questioning my background, abilities, skills and if all the trouble is even worth it. It is exhausting. From my ongoing torment, I offer you a few lessons. For those of you also in the trenches, I hope this is helpful.  

Relationships Over Resumes

People always say it’s about who you know, and I always thought that was a bunch of crap. But looking back on the jobs I have gotten and opportunities I have been given, almost all of them came from women I already knew and had some sort of professional connection with. So do what LinkedIn and all the counselors tell you to do: network. Stay in touch with past connections and use the human resources you have. Yeah, it can sometimes feel awkward, but just remember we are all in this together. Those boss ladies with the dream jobs? They didn’t get there by themselves.

Look for a Challenge

Someone once told me if you meet all the qualifications in a job posting you won’t be a good fit. Think about it: you walk into a job full of confidence, knowing how to do everything and breeze through training with no major questions or concerns. It all comes easy. There is nothing to learn and you are already bored. When looking for a job, look for a challenge. You want a role you can grow into and progress with, so it’s ok not to know everything at the beginning.

Screw the Script

I used to think I needed to have the perfect answers to every interview question. I prepped and practiced them like it was a monologue for Broadway. After the interview, I would beat myself up because I undoubtedly messed up the order of my strengths and had let an “um” slip out in response to that absurd curveball question about a lobster in a sombrero. As appealing as it may sound, people don’t actually want to work with robots. Interviewers typically won’t ask questions you don’t know the answers to. It gets complicated when you try to guess what they want to hear and answer accordingly. Instead, I have found that by trusting myself to answer the questions as they come, I don’t stress myself out in an effort to follow the script I had prepared for myself and I can allow my personality to carry the conversation.

Stop Stressing

Like so many things in life, opportunities come when you stop looking. At the end of my longest relationship with unemployment, I resentfully took a retail job at an athletic apparel company to get me out of the house and keep money in my bank account. After a few weeks, I realized it wasn’t so bad and decided I would spend the next few months stocking stretchy pants and focusing on myself. The next day I received a call from a company I had applied to months earlier and within two weeks I had accepted a full-time job. Knowing I had a plan outside of this opportunity meant I wasn’t resting my hopes, dreams, and financial stability on a series of interviews. I wasn’t consumed with stress interviewing with the CEO, and for the first time allowed myself to trust in the process and actually believe that if it didn’t work out it wasn’t meant to be.

Turn the Tables

You won’t be able to identify every red flag in a few hours of interviews, but any concerns you come away with are usually valid. It is so important to ask questions, stand up for yourself, and trust your gut. The interviewing should be mutual and remember that you can always decline an offer. I used to think this mentality was a luxury, but it shouldn’t be. Making sure the company is the right fit will save a lot of pain and suffering in the long run. Don’t be desperate. There is value in being a little hard to get.

Lose the Ego

Show me a linear career path and I will show you someone who hasn’t been in the workforce for decades. Millennials jump jobs much more frequently than subsequent generations, averaging 4 different jobs, often in completely different industries, by the time we turn 32. Lose your ego and try to be comfortable taking steps forward, to the side, and even backwards if it will ultimately get you headed in the right direction. Admittedly, I am still working on this one.

Patience is the Hardest Virtue

As hard as I have tried, I have never been able to make my dream job magically appear or will someone into sending me an offer letter. While I openly tell potential employers that patience is my weakness, this acknowledgement doesn’t stop me from anxiously refreshing my inbox after submitting an application. Everyone works on their own schedule and it almost never matches up with your own. Accept this fact and your job search--and probably your whole life--will go much more smoothly.

LifestyleVirginia Santy