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How To Become a Job Hunt Strategist with Christopher Taylor

Episode Summary

In this episode we’ll be hearing from Christopher Taylor, a Job Hunt Strategist hailing from Chesterfield, Virginia. Chris’ work experience began with a Burger King broiler and later included an internship at Lizzie Grubman Public Relations, a decade in sales at a large company, and few years as a headhunter before striking out on his own. In addition to his past roles, Chris also shares his philosophy on the importance of identifying your passions as well as understanding the unique skills you can bring to a company.


Full-length Video

Podcast Episode

Key Takeaways

  • Salaries are obviously important because you want to ensure that you can meet your financial responsibilities and obligations. But, be sure to also assess your interest and passion for a career or position. Take the time to think about what drives and fulfills you.
  • A layoff or job loss can be stressful because of the accompanying uncertainty and possible financial hardships. But, these life events can also be an opportunity to leave situations that aren’t right for you.
  • There isn’t always a clear or straight path for getting to where you need and want to be. It can require many small steps that build on each other and incrementally get you closer to your goal.

Learn more about Christopher

Show Notes & Video Clips


Can you give me a brief overview of your background? Where are you from? What were you like as a kid?

  • Chesterfield, a suburb just outside of Richmond, VA.
  • As an only child spent a lot of time thinking, which made him highly strategic and crave interaction with others.
  • Was naturally curious as a kid so always had a million questions for everyone and still does.

What kind of a student were you?

  • A solid B student who really stepped it up in college.
  • Performs a lot better when learning material that he’s interested in and was a lot more connected to the institution where he went to school. Was a lot more connected to his teachers and the curriculum in college than he was in high school. So really excelled in college.

Did you work during high school? When did you have your first job and what was it?

  • First job was at 16 at Burger King during the summer working the broiler. He was the guy that made the burgers.
  • Second job was at a grocery store where he worked for a number of years. He was a cashier as well as the guy that ran the groceries out to the car so he interacted a lot with customers.
  • Had another job at Enterprise Rent-A-Car cleaning the cars. You wouldn’t think that cleaning cars would be much fun but he really enjoyed the independence of the role and doing his own thing.


What attracted you to Hampton University?

  • Looking at his family background, everyone went to an HBCU. Everyone either went to Virginia State University or Hampton University. He always wanted to go the HBCU route and Hampton was where he wanted to be.

Tell me about your major. What inspired you to pursue that course of study?

  • Chris majored in broadcast journalism after being inspired by a communications class that he really enjoyed and his family being really into the news.


How was your transition into the working world?

  • Around junior year (third year) of college he realized that he didn’t want to do broadcast journalism and didn’t want to be on TV.
  • He had a couple of internships that exposed him to the world of radio and interned at a radio station for a summer.
  • Chris had an internship at Lizzie Grubman Public Relations, a top PR firm in Manhattan (New York City).
  • Those experiences gave him a mix between media and the business side of things.

Following the graduation from college and moving into the working world, how prepared did you feel for your career?

  • Prepared from the standpoint of being a great writer that could communicate well and prepared from a confidence standpoint. Prepared from the standpoint of prior experiences, internships, curriculum, etc.
  • Where he did lack was the tech piece. When Chris was in school they didn’t have the same technology as a lot of other colleges. Being an HBCU maybe the funding wasn’t there but the tech piece was missing so he was a little bit behind from a tech standpoint. He had to learn that on his own.
  • As far as what he would do differently when he first came out of college was going into the opportunity based upon what they were willing to give him and the amount of perceived stability. He would go back and do a better job of taking the time to assess his passion even if it meant starting at a more humble compensation level.

What led to you leaving that position or what pushed you to your next role?

  • Chris was never passionate about what he was doing, the product, or the customers. He didn’t mesh well with the corporate culture as it was a very conservative company.
  • When he initially started with that company it was after he’d graduated from school in 2004. It was a very different landscape at that time and if you were working for a Fortune 500 company or a large company you had a lot of stability.
  • Now large companies are going through corporate restructurings on an annual basis. By the time Chris had been with the company for about ten years he’d started going through restructurings regularly and ended up getting laid off. He really didn’t expect it but it was the best thing that’s ever happened to him in his life.
  • He didn’t have the courage to walk away from a situation that wasn’t right for him. Getting laid off kind of forced his hand which was a blessing.


You’ve since moved on and at present you’re now a Job Hunt Strategist. How did that come about?

  • For the first time in his life Chris had an opportunity to evaluate what he was passionate about.
  • As he was going through the job hunt everyone was compassionate about him having to go through what they thought was a rough job hunt process. But, Chris was actually having an amazing time and loved hunting for a job.
  • He sat down with with over 100 individuals and had a lot conversations. He wrote a list of companies that he wanted to work for and those conversations led to the number one company on his list. Chris landed a job at the number one company on his list because he was willing to have 100 conversations with random people just to see where they went. Each conversation got him a little closer to where he wanted to be and each conversation taught him something new.

And you are currently self-employed, correct?

  • Chris got the job that he was looking for with the top recruiting agency and became a headhunter where he worked a nationwide desk for about two years. He worked with people from all over the country and some international where he basically connected people with an opportunity.
  • He ended up walking away from that situation because when you’re a headhunter your loyalty is tied to the companies that you’re serving. And if you’re serving great companies that’s awesome.
  • But he had a lot of really bad clients too and people that were just jerks who were going into the hiring process with malicious intent. And that’s something he wasn’t comfortable being a part of.
  • And that’s when he came up with The Occupation Optimist which was basically taking all the secrets that he’d learned and helping the everyday job seeker find their next role because the average person doesn’t know how to find a job.

What does an average day look like now that you’re both working for yourself and also helping people find positions that they can also be passionate about?

  • On an average day you Chris does some business development. So for maybe an hour he’ll make a post on LinkedIn. At one point in time he was writing a lot of articles for The Muse, Business Insider, Time Magazine, Black Enterprise, etc.These features made people aware of the fact that he exists and what he brought to the table. A lot of word of mouth.
  • There were a lot of individuals coming to him asking for help with their resum√©, LinkedIn, networking strategy, and job hunt strategy.

How do you personally define success?

  • For Chris success is linked to happiness, fulfillment, and peace of mind. He believes that if you can find a way to feel fulfilled and happy on a daily basis as well as having peace of mind then you are successful. Because it’s not easy to check those three boxes.

Would you say that the current reality of your career has fallen short, matched, or surpassed your your aspirations and expectations? Based on your own definition, would you say that you’re successful?

  • “Yeah, I think that I am successful. I absolutely love what what I’m doing and I can’t wait to continue to grow and and touch more people and help more people land the job that they want versus the jobs they feel like they have to take.”


What goals are you planning or currently pursuing?

  • Looking forward to doing more international work.
  • Working on putting together a video or a an e-learning course which would help to reach people around the country and the world. So it’s like basically you get this video and you pull out your laptop and then you can be sitting in your bedroom with your laptop in your lap at 2:00 in the morning. And go through the video and get all the information that he would give to his everyday client.

Is there any other career or life advice in general that you would offer to your younger self or any other young person that’s still in school, getting ready to enter the workforce, or trying to navigate their early career?

  • Think about what you bring to the table and what area of your collegiate experience can you maximize. Think about what makes you stand out. What do you do better than your peers. And lean into your strengths.

Imagine it’s years from now and you’re nearing or already retired. When you look back on your career, what accomplishments or achievements would make you consider it a roaring success? What would you be proud of?

  • Would be most proud of helping people who are underrepresented in some way.

Have you read any books that have been inspirational or provided some sort of guidance for you with regards to your career?

  • Loves to read any type of self help books. Also loves to read any books that give exposure to other cultures, other groups of people, other ways of life, other religions.
  • Currently reading a book called Half Broke Horses by Jeannette Walls who is also the author of The Glass Castle which is one of his favorite books. Half Broke Horses is a really cool book about a woman in rural America in the early 1900’s that wants to be a career woman.
  • Also reading a book called Ask and It Is Given by Esther and Jerry Hicks which is basically about the benefits of positive thinking.

Have there been any other people (famous or only known to you) that have inspired you or shaped your career?

  • Chris is close to one of his first cousins, like brothers. At one point in time he was a financial analyst or broker at Goldman Sachs and was making an obnoxious amount of money. But, he ended up leaving his job, moved from New York to Atlanta, and opened a restaurant. Everyone thought he was nuts.
  • But, he was able to walk away from a situation or an industry that made him uncomfortable for whatever reason and pursued what he was passionate about. He always pushed Chris to do the same.
  • “And it took me a long time before I was able to put together the courage to actually pursue what I was passionate about. But, if it wasn’t for him kind of pushing me, planting that seed, leading and showing me that it could be done, I would never have given recruiting a chance. And now I see, you know, now that I work with individuals, job seekers on a daily basis, people all across the country, all across the world. Now, I see that making those transitions is not unheard of by any means.”

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