Dear Pathfinder: Not Feeling Good Enough 

Dear Pathfinder is the Career Center’s Career Development advice column. Have a question for Dear Pathfinder? Submit it here. Catch up on past letters, here.  

Dear Pathfinder, Not Feeling Good Enough  

Searching for flexible remote positions in areas of interest and not having success despite experience. What is the best way to prove worth despite age? 

— Not Feeling Good Enough 

Dear Not Feeling Good Enough, 

First things first, you are NOT alone! And I mean that in so many ways. One of the most common questions we have is usually centered around breaking into the industry while having the required skills, but also feel like the majority of the opportunities are for “seasoned” folks. In some instances, that may very well be the case. Employers may consider certain qualifications or years of experience they are looking for in a candidate. You may fulfill that requirement, but you also must remember that you may be one of MANY applying for that same position and the experiences presented within the candidate pool will vary. In no way should this diminish the skills you have acquired or make you feel “less than”, think of it as “this one was just not meant for me”. 

My solid advice would be to keep cultivating your skills and for sure do some great networking! Resources like the Duke Alumni Directory and Ask a Blue Devil are great places to start. You want to meet people and develop working relationships so that your name and work can come up in rooms and conversations where you are not. THAT is the biggest resource you will ever be able to develop. Remember not being selected as the final candidate is part of the process as well. Be confident in your work as you know how much you have put into building your skill set. Use the advisors within the Career Center for some different viewpoints and don’t forget that some of the staff and faculty you’ve met along the way are great resources as well. 

Remember what I said earlier, you are not alone. And, if you ever feel like you are, please stop by the Career Center. I can almost guarantee you’ll be greeted with open arms and open minds to help you navigate this process. Keep strong in knowing yourself and take a little advice from Jay-Z to keep in your pocket: “A loss ain’t a loss, it’s a lesson”. 

— Career Advisor


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Submit your questions about navigating your career journey here. It’s anonymous! (Questions may be edited for future use) 


Dear Not Feeling Good Enough,   

To the best of your ability, remember that sometimes it isn’t about you. While it’s easy to say when you’re not navigating the job search, this truth often goes unsaid. You can be well suited for the position, but the pool is competitive, or other reasons beyond your candidacy may rule you out.  

It’s also important to raise that you may have an urgency to land a role because you have bills to pay. If this is your reality, I would advocate for you to find a job first that will allow you to cover your bills while you continue searching for your ideal remote position.   

It may be time to review your resume and cover letter as you explore the best way to showcase your skill sets. Sometimes you may need to be more intentional with highlighting your ability to perform the responsibilities listed for the role. As you review the job description, consider which skills they are asking for. I wouldn’t encourage you to shoot for perfection, but the idea would be to ensure everything you include on your resume is there for a specific reason.   

Is it time to consider networking in the spaces you’d like to go? Are there professionals in the field who you think could shed light on how they’ve gained experience in the field or landed their current positions? Informational Interviewing is a great place to start if you’re new to this.   

— Career Advisor

Hear from our first guest contributor, Earnest Steward, a Human Resources Industry Professional

“First things first – your worth goes beyond the impact story you convey in an interview or the outcomes you deliver on the job. Work / Career can feel defining in so many ways but be encouraged and know that you ARE good enough; sometimes the world just needs a little time to catch up before it ‘puts some respect on your name’.

As for ways to break into your desired industry, I agree with what’s been said on skills development, refining your story, and networking. Succinctly conveying how you’ve applied your skills to deliver value equips the right person with the data they need to trust and advocate for you. Furthermore, as more corporations move to skills-based hiring approaches, projects are the new currency. Perhaps there are opportunities in your network (it’s bigger than you think) to contribute to a project that hones a skill or yields an outcome relevant in your target industry. The more of of these you have in your pocket, the better.

Lastly, as you look for flexible or fully remote options, you can strengthen your candidacy by demonstrating how you’ve been successful working in that context. When making hiring decisions, companies want to feel confident the candidate will get up to speed quickly and be successful in the role. Your skills and historical performance obviously play a part here but there are also the intangibles – the lessons you learn in your career about how to navigate professional spaces effectively. This includes things like who to ask for help and when, how to influence without authority, or operating at the right level of autonomy. If you don’t make this part of your story clear, a hiring manager may feel it’s a safer bet to hire the more seasoned candidate because they assume the seasoned candidate is better positioned to navigate professional environments with less support.”

Keep grinding. The opportunity will come.”

— Earnest Steward, HR Industry Professional

By Jared Smith (He/Him)
Jared Smith (He/Him) Associate Director, Diversity, Equity, Inclusion and Belonging