What eight role changes in 12 years taught me about job hunting

Why confidence matters more than credentials + practical ways to build it when you’re feeling insecure

I’ve had eight jobs in 12 years, which means I’ve done a lot of interviewing.

Here’s what I’ve learned: the most important thing you bring to a job hunt isn’t your resume — it’s your mindset. I’ve rarely gotten what I want while leading with desperation, insecurity, and fear.

Leading with confidence is easier said than done, but I don’t believe in a fake-it-til-you-make-it approach. I’ll share a few tips I’ve picked up over the years, but first, I’ll tell you about one particular experience that crystallized this realization for me.

In 2019, I was hired into my first brand-direct marketing role with zero experience in brand-direct marketing. My confidence was delusionally high during the interview process. I had done well in media and was ready for a new challenge. How hard could it be?

As it turns out, it was pretty fucking hard. I was the first employee at a small CPG brand with minimal funding and no marketing leadership. Quickly, I realized I had no idea what I was doing, and the business itself was fighting uphill battles that marketing alone couldn’t solve. I blamed myself anyway.

After two-ish years of rocky company performance and an even rockier mental state, I decided to look for a new role with a bigger team. My confidence was at an all-time low, and I thought I had nothing to show for my hard work. I was running social, influencer, email, growth, creative, and retail, and doing none of it well. I didn’t have flashy metrics like revenue growth or Instagram engagement to flaunt on my resume.

Needless to say, I was a big ball of nerves going into interviews. I felt desperate. My mindset was: “Please, someone take a chance on me.” I didn’t know my worth, so I couldn’t lead with it.

I stumbled through interviews for a few months without meaningful progress. Eventually, I started receiving projects as part of the hiring process. My first reaction was almost always terror, but as I worked through them, I began to prove my value to myself. I was delighted by my ideas and impressed by my strategic thinking. I started to hear a new, kinder voice in my head: "Maybe I am actually good at this."

Those projects were the turning point. My job hunting luck didn’t reverse overnight, but it started to shift. Four months later, I landed my role at Harry’s, working on the Flamingo brand. I was confident I’d get an offer as I was completing a case study, and for the first time, I was right.

Grateful for the friends who kept me sane during my summer of job-hunting hell

I’ve gone through smaller cycles of this process in more recent years, doubting my leadership skills, my worthiness of a certain salary, and my ability to shift into new industries. I imagine this will continue throughout my career, but I now know how to navigate it and what to expect.

If you’re anything like me, you’re more likely to get what you want if you feel both capable and deserving of it. That might seem impossible depending on your current situation — maybe you were laid off, fired, or suffered a bad manager who destroyed your self-esteem — but here are a few tips that have dramatically helped my job hunting mindset:

1. Prep for your interviews

I’m not just talking about a Google search and a quick scan of your interviewer’s LinkedIn profile. I’m talking about intentional and effortful preparation. If you’re feeling insecure and are worried you won’t be able to articulate your value or skills, read through the job description, make a list of 5-10 questions you might be asked, write out your answers, and practice them in the mirror. Dina Fierro has a great ChatGPT prompt for this to help save you a bit of time.

So what if you don’t have impressive sales numbers or press hits to show for your hard work? You’re a marketer. Tell me a different story — one about your determination, grit, and scrappiness. Startups will love it, trust me.

2. Find an expander

I’m borrowing the “expander” term from To Be Magnetic, but this practice has always seemed evident to me, although I didn’t have a word for it. An expander is someone who has achieved something that you want. By observing them, you start to expand your idea of what’s possible for you.

Here’s an example: Suppose you want a director-level role but are worried about your ability to land one because you only have four years of relevant experience. Put your LinkedIn stalking skills to good use and find three people who have your dream title with only four years of experience. It’s crucial they have a similar background to you — if they have an MBA but you don’t, they likely won’t be a great expander so long as you perceive education level as a fundamental difference.

Bonus points if you reach out to them for an informal coffee chat to learn how they did it.

3. Lean on your community

Feedback is a gift, especially when it’s coming from people you love and trust.

I often ask my sister, friends, and boyfriend to review my projects, listen to a presentation, read my thank you notes, and practice interviewing together. Job hunting can be lonely, but it feels better when you engage your community. Both gentle constructive criticism and emphatic praise have helped me build confidence when I was feeling down.

4. Commit to a compensation requirement

The biggest base salary jump I’ve made with a new role was $40k.

The offer I got was well above the range listed in the job description. How? I was crystal clear about my number from my very first conversation with the recruiter. Sure, I got some pushback, but instead of lowering my expectations, I doubled down by reinforcing my why whenever the topic of compensation came up. I was prepared to walk away if the offer didn’t meet my requirements because I believed I could find it elsewhere.

If you’re in the position to do this (and I recognize not everyone is), make your number a non-negotiable and stick to it.

Use Glassdoor, Levels, and similar boards to find ranges for the role you’re looking at based on your experience and location. Ask your coworkers, friends, partners, and family members what they make. Aim higher and watch what happens.

(P.S. I just got access to Creative People’s Salary Benchmark Report so check that out, too).

Job hunting is just as much about proving yourself to you as it is about proving yourself to someone else. And I know I’m not the only one who’s had to learn the hard way.

What’s the best mindset shift you’ve made while job hunting? And how have interviews felt different when you were confident vs. when you weren’t?