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I Answered 15 of Your Most-Asked Career Questions from DMs

Including the bold question to ask in your next interview.
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A few weeks ago, I asked in my Stories if you had any career-related questions, and within an hour, my DMs were flooded. While I answered many of them on Instagram, there were so many I couldn't get to, but still found myself thinking about days later. Here are my answers to 15 of your most-asked career questions:

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I learned so much from our first employee Phoebe, who transitioned from our first Editorial Assistant to our Art Director. One of the challenges of having such a small company, especially when you’ve carried the majority of the workload for so long, is putting structure in place and outlining processes everyone knows to follow. Phoebe worked with us for almost three years and remains a close friend to this day, but if I could do one thing over, it would be to give her job a more concise structure and provide clearer instruction as a manager.

At the time, we were literally huddled around a set of desks in our guest room, so finding the balance between being a small, family-run company and later transitioning to the company we are today was always a work in progress (and still is). With that being said, I try to be much more concrete with work-related parameters I give these days, including everything from the hours we expect our employees to keep to expectations for each role.

Naturally, as the company has evolved, the delineation between roles has become more distinct. Leslie, G, and I no longer have to be Jack of all trades (at one point, G was the photographer/HR Manager/President/COO). The clear-cut delineation we’ve evolved to helps avoid a lot of confusion around the office.

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One of the things I love most about my job is that it keeps me on my toes. Every single day looks different, so some mornings I’m up at 5:30 answering emails, and some Sunday afternoons I'm going through linesheets for the Shop. I try to keep as traditional hours as possible, which for me means weekdays 9 to 5. I generally work from home in the morning so I can prep for the day and check my email over coffee, then go into the office between 9:30 and 10:30 and leave around 4:30 or 5:30. If I need to pick up Sloan from school I'll leave a little earlier, which G and I switch off doing when our nanny isn’t available.

It’s also worth keeping in mind that I’ll occasionally film a Story or IGTV for Instagram at home, immediately run out the door, and then end up posting a makeup tutorial I filmed at 7:00 am three hours later. In this way, social media isn’t always a perfect representation of the exact times I’m doing things.

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Whenever you don’t hear back after a phone or in-person interview, it could mean one of several things happened, many of which likely have nothing to do with you. There may have been something that happened personally or internally in the company—the role may have dissolved, or they found someone else. However, none of these things justify crickets (everyone has time to send a 30-second email to an applicant). I had that happen once when I interviewed at a major fashion company and even though I knew from the interview that the office culture was not what I was looking for, I was always taught to sprint through the finish line just in case. Follow with a handwritten note and email (but never to the point of being and annoyance). Even if they never get back to you, at least you know you did everything in your power to be a stand-out candidate. Then, be sure to not get hung up on it and instead, move on. Recognize it wasn’t meant to be and with more searching, you'll often find something even better down the line.

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Business casual walks that fine line between looking too corporate and coming off as stuffy or out of touch, and dressing too casually with cut-offs or something promiscuous. It’s a perfect place to apply the High/Low strategy, but with “Business Professional” being High and “Casual” being Low. You can wear jeans, even sometimes with distressing depending on your office, and a tee (Low) as long as you pair this with a structured blazer and heels to pull the look together (High). If you’re wondering what to wear to a new job, look to see what other women in the office are wearing during your interview process. You can even ask the person you’re interviewing with about appropriate office attire.

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It all has to do with your perspective. First of all, recognize that you’re not alone in feeling stuck, either in your role, company, or even profession. Then, make sure you have open communication with yourself and your manager and/or coworkers about the elements you’re unhappy with. Talk with them, and try to see if there are any steps you could take to feel inspired again like taking on a new project. Focus on and lean into the parts of the job that once attracted you to the position. If that doesn’t work, it may be time to start looking for a new role—but be sure to explore your options before jumping ship.

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I think it’s a very rare instance in which you can find yourself in a work environment in which everyone gets along flawlessly. When there are differences between you and other people, try to create a respectful, professional separation and make a clear delineation. Recognize that a coworker isn’t necessarily the same as a friend you’ve chosen to spend time with. In the case where someone is negatively impacting the work you do, or sabotaging you by stepping on your toes or taking credit for work you’ve done, I think being an open communicator is of utmost importance. Address the issue(s) with them in a way that is firm, but not aggressive. If conditions don't improve, it may be time to go to your or their superior. Either way, always follow up via email so you have a written record of any issues.

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My inner critic is something that’s plagued me from playing sports growing up to getting certain grades in college, and I’m proud to say that I’ve made some very big strides in the past year, largely through therapy. Instead of expecting myself to do things perfectly, I now recognize the important of making mistakes and learning from them.

Mistakes are valuable. As business owners, G and I try to instill that same forgiving approach to our employees. When you make a mistake (because it really isn’t a case of if but when), how you respond to the mistake says a lot about who you are. First, acknowledge the mistake (and bring it up to your superior before they have to find out about it through other means). Next, if the mistake was your fault, own up to it and apologize, which is much more impressive than immediately getting defensive and making excuses. If you can fix it, that’s great, but try to come up with a solution for damage control and to avoid it happening in the future. In short: Admit the mistake, assume responsibility, and provide a solution to the mistake as well as a plan for avoiding it in the future.

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To be honest, this is a hard one for a candidate to come back from, because it indicates a lack of respect and often, general disorganization. I’m looking to hire individuals who are punctual, detail-oriented, and able to plan ahead—traits that aren’t aligned with being late to an interview. That being said, unexpected traffic and unforeseen circumstances happen to even the best candidate, so like making any mistake, it comes down to how that person reacts. If they saunter into the interview without mentioning it, it’s probably not a good fit. But if they arrive and are apologetic, and acknowledge it in a prompt follow-up email or handwritten note, all would be forgiven.

To that end, all the small details, like arriving on time, matter in an interview as much as what you say and your previous experience. I notice how firm your handshake is, if you say “thank you,” if I bought you a coffee at the interview, what you’re wearing, etc.

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Travel and being away from my family is part of my job, so I try to not stress about it too much, and when I’m home with my family, I make them my priority. There are certainly sacrifices, like this past December, when I had go on a 24-hour work trip and miss the Sloan's holiday dance performance she had been practicing for months. It made me incredibly sad, but I did everything I could before and after the trip to let her know I was thinking of her. I went to the dress rehearsal and had G Facetime me with Sloan immediately afterwards. And at the end of the day, everything I do for work ultimately comes back to benefit them, so I do my best to maintain that perspective.

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In some ways, you should approach your relationships at work the same what you do friendships—you shouldn’t let anyone feel like you aren’t respected once you’ve proven your worth. With that in mind, it’s also important to be proactive in the workplace. There’s nothing more annoying to a busy manager than someone who’s constantly asking, “What can I do?” Whenever possible, try to be proactive and take on tasks before your manager asks you to do them. But, if there truly isn’t enough work to be done and you aren’t feeling inspired to take the initiative, it may be time to start looking for another job.

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I start most days by making a comprehensive, handwritten to-do list. Some tasks are less-time intensive, like answering emails, and others are much larger projects I won’t necessarily be able to finish in one day. But writing it all down helps me gain a better perspective on everything I have going on, so I can tackle it as I go. I’ve heard the best thing to do is tackle the most intimidating tasks earlier in the day, but I get overwhelmed and paralyzed. I also do some of my best work under pressure, so I personally start with the bite-sized items on my to-do list, then work up to the larger tasks.

If I’m feeling particularly overwhelmed, I’ll go back through and number things in order of priority so that I’m sure I’m taking care of the time-sensitive projects first.

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Anyone can feel susceptible to feeling unmotivated, and I’ve absolutely gone through phases, even though I love so much about my job. Just remember it’s totally normal to feel this way. I like to remind myself that you need those moments of feeling blah to really be able to embrace the times you’re on fire, when everything is great. Personally speaking, when I’m feeling blah, it’s often a signal I need a little space from work. You can’t always take a week-long hiatus or slip away for a long weekend, but getting away from my desk and going for an hour-long walk at lunchtime helps me hit the reset button.

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This is specific to my job, but applies to anyone who’s experienced phases of burnout. To me, it’s about being able to recognize the days when I’m not feeling inspired or having a lot of ideas and calling it a day. Then, there are days when I’m flooded with ideas. Sometimes I’ll leave an editorial meeting, then shortly after be driving in my car, and need to call Leslie because I’ve thought of even more pitches. Any time I’m in a funk, I know I'll always get out of it.

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Within our company, I’ve worked hard to create an office environment in which people always feel comfortable and confident to come to their managers with feedback, suggestions, and complaints. Having an open dialogue is so important to growing as an employee and a person.

One of the unique benefits of cupcakes and cashmere is that there are so many channels for people to reach us, through our e-commerce customer service (which goes directly to our team), editorial inbox (again, directly to our Editors), Facebook community, social media DMs and comments, and comments on the blog. I always love hearing from people (as long as it’s not just negative for the sake of being mean, but instead, constructive criticism), hearing what readers and customers are loving and want more of, and what’s lacking from their experience. We always do our best to take into consideration as much of this feedback as possible—we bring notes from comments and emails into every editorial meeting, in addition to analytics—while maintaining our own goals for the company.

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One of the things most people forget to do is say how much they would love the job. At the end of the interview, it’s your last chance to reinforce how good of a fit you are and how passionate you are about it. It’s always impressive when someone reiterates how interested they are in working for our company, after they’ve asked thoughtful questions and listened to our comments about what the job would entail.

Another thing I would recommend doing, only if you feel confident enough, is to say “After speaking with me, is there anything that would lead you to believe I’m not a good fit for this role?” It sets the tone for having a really transparent and honest conversation, and allows you to address any hesitations head-on. Leslie did this in her interview, and it opened up the conversation for me to tell her I was hesitant to hire her since she lived in New York. I was concerned she’d change her mind about moving cross-country, or not like Los Angeles and maybe even move back to New York a few months later. I don’t take team-building lightly and wanted to feel confident that, if we offered her the position, she’d be in it for the long-haul, as far as she could tell at the moment. She ensured me she was happy and able to make the move, and the rest is history!

P.S., I answered many of your career questions in my Instagram stories which I saved to the FAQ highlight here! x

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