Your Most Common Career Questions, Answered

Every month, I ask the #SilbSquad what questions they have on a specific topic. For March, we’re talking all about careers and I’m answering the most popular questions you had below!

Q. If they make an offer, how do I negotiate without seeming ungrateful?
A. Repeat after me: NEGOTIATING IS NORMAL. Employers expect you to negotiate. Most of the time, the offer they’re giving you is lower than what they can actually pay… because they’ve built in room to accommodate for negotiation. I would argue that if you accepted the first offer, they’d probably be wondering why you didn’t ask for more. It shows that you’re assertive, confident, and that you know what you want & deserve. (Men seem to be MUCH better at this than women – they literally don’t think twice about it. Meanwhile, we as women get nervous about appearing greedy or ungrateful. Read this book! It truly changed my life and perspective on this topic.

Q. Is the “gap” in your resume a big deal anymore? Thinking of taking 3 months to move/get married.
A. I definitely think that attitudes toward a gap in your resume have changed over the past few years—especially coming out of the pandemic. With so many people being furloughed, laid off, taking care of sick family members (or themselves), having a resume gap now seems more common than ever. LinkedIn even has a new feature dedicated to it! Bottom line: if you’re the best candidate for the job, a good employer is going to hire you regardless of a three month gap.d a new balance, and unfortunately you’re in the crosshairs of that.

Q. Dream job burnout. How to navigate whether it’s time to leave a role you love.
A. I so relate to this, because I went through the exact same thing. When I left my job at Town & Country, it truly was my dream job. It represented everything I had spent over a decade working toward… so the idea of leaving felt foolish. But I couldn’t ignore the feeling in my gut that was telling me it was time to take a risk and try something new. Eventually, I decided that if I stayed at my job, I would always be wondering “what if.” So I took the leap, and it was the best decision I ever made. I also had the realization that your “dream job” can truly evolve over time!

Q. Can you talk about changing careers/making a switch? Looking to do that myself!
A. This was by far the most commonly asked question… so just know that you’re not alone in wanting to make a change. I know the idea of “transferrable skills” sounds trite and cliche, but it’s true. Matt (my husband) went from a career in finance at an investment bank to working in sales for a luxury fashion brand. When he was interviewing for the new role, he really played up the skills and aspects of his experience that would be relevant—he’s great with numbers & financials, thinking analytically, managing money, assessing risk, dealing with people, etc. He also showed how passionate he was about the brand/product/industry, despite his lack of experience, which I think really helped to seal the deal.

Q. How to know when to delegate vs doing it yourself?
A. This is something I struggled with a lot in the beginning of starting my business, and it’s something I still struggle with to this day! The best piece of advice I can give you is to ask yourself: Am I the only one who can do it? Am I good at it? Do I enjoy doing it? Is it taking me away from more important revenue-generating responsibilities? Personally, I knew it was time to hire a manager to negotiate my contracts for me, because my answers to the above questions were: No. Not really. Not at all. And yes, absolutely.

Pro tip: The #SilbSquad Facebook group is an amazing resource for career advice and #nonawkwardnetworking. If you want in, just be sure to answer all 3 questions. Hint – the answers to the first two are rosé & Matt.

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