Your Career Questions Answered and Black Pants Styled 3 Ways

February 11, 2020

Black Pants Three Ways I wit & whimsy

As someone who has been in the workforce for a long time (I had my first job starting as a junior in high school in 2001 and have worked jobs in some capacity every year since) and as someone who truly loves what she does, I am passionate about sharing help and guidance when it comes to others finding career fulfillment. The past several years my career content has resonated with you all so the other week I took to Instagram Stories to ask you to submit your career related questions…and boy did you have a lot of them! I hope you have some takeaways and find the following Q&A inspiring as you navigate your own career.

I am also thrilled to partner with Ann Taylor on this post as they are one of my favorite brands to collaborate with and when I saw their new High Waist Ankle Pant at a recent press preview, I immediately knew I wanted to take an opportunity to show them styled three ways. In last year’s reader survey you guys asked for more work wear options for when you can’t wear jeans to the office and I hope you’ll find the following three looks inspiring as you get dressed in the morning Monday through Friday.

Your Career Questions Answered and Black Pants Styled 3 Ways

Black Pants Three Ways I wit & whimsy

Black Pants Three Ways I wit & whimsy

Would love some guidance/tips on obtaining health insurance being self-employed.

Whenever I get this question, I let people know the answer is generally there’s a variety of not-great options. I personally use the healthcare marketplace and have Oscar insurance which I don’t love. The cost has increased over $200 since I first became self-employed and the benefits haven’t gotten better. To pick the plan that is best for you, assess your health. Do you go to the doctor often? Have a lot of medications? Do you have a pre-existing condition? Are you prone to illness? You may want a lower deductible and higher monthly payment. If you’re relatively healthy you can consider a lower monthly payment and higher deductible.

Quick and easy self confidence booster tips in the workplace?

I love this question! I am a big fan of mantras when I have a big day coming up. Try telling yourself silently – or writing it out – something like “I am smart, capable and nothing can hold me back.” Repeat it as often as you need. Also have a “Job Well Done” folder in your email where you can store emails with kudos you receive. It’s handy to have come reviews but also when you need a confidence boost.

Tips for moving abroad for work?

Do your research! Every country is different in what they allow for Visas and in my experience, you need to prove that you are the perfect and only person can do that role if you want to get a work Visa. When I interviewed for jobs in Paris and London in 2015 I found the companies dragging their feet in wanting to pay for my Visa, despite being interested in hiring me for what skills I could offer. Be prepared to go above and beyond to showcase why you’re the right person for the job so that a company wants to front the (very expensive) cost of sponsoring your Visa.

What advice would you give someone trying to build their own consulting business?

Know that you’ll work harder than you ever did when someone was telling you what to do. You will have a new understanding of “hustle” and you will have the potential for finding great career fulfillment. Over prepare before you start out and majorly work on building your network. Be sure to prepare financially by having at least six months of savings that covers all your monthly expenses.

What should I do when the boss I love unexpectedly leaves and you’re in your role without guidance?

Step up to the plate in a major way! This is a great opportunity for you to take on new responsibilities and make your worth known. Make note of what you’re taking on outside of your job description and file it away for your next review. Seek out someone more senior and ask if they are willing to be a sounding board and mentor while you’re without your boss so you feel supported in decision making.

How do I develop a mentorship with someone at my company? What should I look for?

Informally interview those at your company you think may make good mentors. Ask them if they’d be willing to get lunch or coffee and that you’d like to hear more about their background, role and what they are working towards. You can learn a lot about a person during this time and have a gut check if it is a relationship you’d like to foster into a mentorship. And think if there’s someone you can mentor! Being a mentor can add fulfillment to being a mentee.

Is it very hard to break into PR in the U.S. if you’ve worked in PR in a different country?

Foundational skills are foundational skills but I’d say be prepared to do the work in regards to who is who in the U.S. press market for the clients you’d be working for. So much of PR is about relationships with press so you’d need to start to learn who the important editors are and begin building relationships with them. Get really familiar with the U.S. media outlets and associated bylines. (I was once turned down for a job at a PR agency in London because they felt I didn’t have British press relationships.)

Any good ways to deal with coworkers not pulling their weight and making mistakes?

Keep track of every instance of coworkers not delivering or not meeting expectations. And try and set boundaries and deadlines to help them better perform. If they are disrespectful of those and if/when things come to a head, bring the examples of dropped balls to management and ask for help crafting a solution.

How do you know when you’re ready to make a life altering change in your career?

You’ll know when you reach your tipping point. I hit mine in 2015. In that moment give yourself the space to step back and re-evaluate what you’re looking for out of work. See also: how to get out of a career rut.

My office is doing a re-org and I’ve been around the longest. Does the big office matter?

For too much of my career I focused on titles and things like offices and working on the most notable clients. And I wish I hadn’t. What’s more important in my opinion is fulfillment in the work you’re doing. If you love your coworkers then maybe don’t isolate yourself from them and the camaraderie by seeking out an office. Determine what’s most important to you in your work and lean into ways to further that.

How did you go about starting your blog business? I want to have a blog and stylist businesses. 

My blog gained major momentum when I started treating it as a business instead of a hobby. Build out marketing materials to put your best foot forward for every opportunity that comes your way. Track your income and expenses and consider incorporating so you can get business bank accounts and a credit card associated with your blog. Strategize how to get additional readers and followers and set goals for yourself so you’re holding yourself accountable with growth.

Any advice for someone who is just beginning to work post-college?

Know that you don’t need to know how to do everything right away but keep learning. Be the person everyone can rely on. Do every task with a smile. Have poise and exhibit common sense. Always over-deliver. Do what’s been asked of you and then do more. It will make you memorable. Be extremely detail-oriented. Have you double checked your work before you submit it? Is the formatting perfect? Have you gone above and beyond? Find opportunities to network in both your office and in your industry. Your next great opportunity will most likely come through this network.

Remember that some of your most stressful or overwhelming projects or clients will be the ones that are defining moments in your career. They’ll often be the ones you come to reference for years to come when you need examples of your work. Push through and remember things will always improve and you’ll be grateful for the experience in hindsight. And take time to figure out your work style and the boundaries you need to make yourself the best version of your work self. Work will take advantage of how much you give – remember that you are ultimately in charge of your own work/life balance. Finally: work hard and be nice. The true keys to being successful in the work place.

Any skills you’d recommend building early on in your career?

Think differently. Sure, there’s ways that things may have always been done in your line of work…but is there a better way you can propose? Fortune favors the bold. Research conferences you can go to and classes you can take in areas of your career that interest you. I personally wish I had taken more PowerPoint classes and learned InDesign. Nowadays you can also learn so much from the comfort of your desk through resources like Skillshare and YouTube. And don’t be afraid to ask questions!

What are your best tips for starting out as a freelancer / consultant? 

Prepare, prepare, prepare before you go solo. Prepping for six months before I left my corporate job was the best thing I could do. I took loads of meetings with others that were self employed and gained insight and tips from them . They each became a part of my network and I continued to foster those relationships I built. 100% of my consulting work comes from word of mouth so take as many in person meetings as you can. I will talk to anyone once – you never know where that conversation will lead.

And do a lot of the admin work it takes to set up your business while you are still collecting a paycheck from your employer. I incorporated my businesses, got my business banking up and running and a lot of other to dos all done while I was still at my last corporate job. I wrote this article about five ways to prepare for self employment that may be helpful, too.

Any strategies on how to get a job in New York City when you don’t currently live there?

Remove your home address from your resume and proceed with submitting for jobs you find in NYC. My cousin is a corporate recruiter and said it isn’t necessary to include in today’s day in age of email and remote work. Be willing to come to New York and do a week of interviews – pound the pavement and set up interviews even if they are information so you’re getting yourself out in the market. And figure out a way to stand out. If your resume looks like every other you are giving hiring teams no reason to get excited about bringing you on board.

Be creative with your approach to job applications to set yourself apart from the pack of other people going after every role in NYC. As the expression goes, “be so good they can’t ignore you.” And offer flexibility when it comes to getting to NYC. When I moved to the city from San Francisco I offered to start sooner than I wanted so I would land the gig which meant no time off between jobs but instead I worked from the company’s SF offices for the month leading up to my move to NYC.

Can you share tips on negotiating salary and benefits? 

Get as educated as you possibly can about average salaries for your position and standard benefits. See if friends in the industry are willing to share what they make to better inform what you should be negotiating for. And stand up for what you believe you deserve. My first job out of college they wanted me to be a paid intern before assuming the Assistant Account Executive role I was going after. When they indicated this I calmly but confidently explained to HR that with three internships under my belt I was already equipped to do most of the Assistant Account Executive role and that I would be ready to hit the ground running for the teams I’d be supporting as a result. Three hours later I was called and offered the AAE position.

It set my early career up for a better trajectory. I am so glad I took the risk to fight for the role I knew I deserved. And remember that no one is going to give you what you want unless you ask for it. No one is going to fight those battles for you or do you any favors. You have to speak your mind and ask for the things you want and deserve. And have the proof to back up why you’re deserving!

How should I manage receiving one job offer but waiting to hear from others, too?

If you’re curious about other offers it probably means the one you have in front of you may not be the right position. Sometimes it is worth waiting it out at your current job until the offer that really makes you excited. Remember that your career is a long game. Take the time to be thoughtful and strategic about your next move. And remember to trust your intuition!

Do you have tips for dealing with severe burnout without leaving your job?

Share where you are at with your manager in an honest and transparent way. Ask them to help find a solution that allows you to find a better work life balance. This could be asking for one day a week to work from home or additional vacation days. It could mean asking for support in the form of an associate under you so you can better delegate and get better work outs. Before you have this conversation, prepare for it with a list of things you think are causing your burnout. Is it a never-ending to do list? Too long of hours? Benefits not being taken advantage of? Coworkers not pulling their weight? Assess the situation carefully and try and determine solutions to each that you can talk through with your manager.

How do I transition between fields? 

After you determine what field you’d like to transition to, take time in your current role to get as educated as you can on the field you’d like to enter. Read up, watch YouTube videos, network with people in the field and re-work your resume or portfolio or website to begin to reflect the field you want to switch into. Consider shadowing someone in the field to ensure you’re on the right track of wanting to get involved in that industry. When you’re ready to make the switch, ask contacts to make intros and take as many meetings and informational interviews as you can. Be sure to think of ways to set yourself apart so people will want to take a risk with someone with potentially less relevant experience for certain roles.

Any tips for networking in a non-transactional way?

The biggest thing I feel is missing from networking these days is follow through. People take and forget to circle back and keep in touch. I can’t believe how many people I have managed or mentored over the years who ask for guidance or help and then never circle back to say thank you or to tell me how circumstances net out. They ask for my time reviewing their resume, making connections, being a reference, taking a meeting to get help, etc. etc. etc. And then I don’t hear from them again. If I get a lead or a referral from someone I always look to remember to go back to the person who recommended me to thank them, give them a little gift or a referral bonus of sorts. Much of your career will be guided by who you know and people always remember how you made them feel.

I also think events are a great way to network and build your circle. Check out co-working communities like WeWork and The Wing. See if you can join a friend for one of their many events to see who you meet. Also look at Facebook groups in your field or the areas in which you are interested. Have favorite bloggers? Join their Facebook groups or attend their reader meet ups. Consider doing something less “business-y” feeling, too such as starting a book club with 1-2 co-workers who can bring 1-2 of their friends. See who you meet and if you think you’d like to get to know someone better invite them for brunch or coffee. Attending conferences like Create & Cultivate events are also a great way to meet people who are interested in networking.

. . .

Your Career Questions Answered and Black Pants Styled 3 Ways

Your Career Questions Answered and Black Pants Styled 3 Ways

Black Pants Three Ways I wit & whimsy

Black Pants Three Ways I wit & whimsy

Black Pants Three Ways I wit & whimsy

Your Career Questions Answered and Black Pants Styled 3 Ways

The Ann Taylor High Waist Ankle Pant fit like a dream – truly I gasped when I first put them on as I couldn’t believe how good they looked and how much I loved how they felt on. Plus I particularly love the cuff detail on them. In my 2019 reader survey a lot of you asked for more work wear ideas. So I think a well-fitting pair of black pants is one of the best and most versatile pieces you can have in your wardrobe. If you don’t have a pair of little black pants you absolutely love now is the time to change that. And I have to say the quality on this pair for the price (just $89) is exceptional.

My three looks were inspired by little black pants for 1. an important meeting, 2. little black pants for a day you want to go to drinks or dinner after and 3. little black pants for travel or more casual days. The sneakers in the third look can easily be swapped out for heels once you reach your destination. Get yourself this pair of versatile pants (and do share – which look is your favorite!?)

Look One:

Ann Taylor High Waist Ankle Pant (Size 4) // Puff Shoulder Top (M) // Chesterfield Coat (Petites M) // Twiggy Suede Bow Flats (Size 6.5)

Look Two:

Ann Taylor High Waist Ankle Pant (Size 4) // Seasonless Sweater Tee (M) // Tweed Pocket Jacket (M) // Mia Suede Pumps (6.5)

Look Three:

Ann Taylor High Waist Ankle Pant (Size 4) // Puff Sleeve Twist Tee (M) // Two Tone Trench (S) // Soludos Sneakers (7)

Some additional noteworthy Ann Taylor New Arrivals:


p.s. more career content and the better habits I am practicing this year.

This post is in collaboration with Ann Taylor. Thank you so much for supporting the brands I love to work with! You can see our last collaboration here.

[Carter Fish Photography]

comments +

  1. Jamie says:

    I’ve been looking for a black pant that is dressed up enough for the office but comfortable enough for day-to-day wear (for travel – need things to do double duty) and these look great! I don’t know why I didn’t think of Ann Taylor sooner.

  2. Kate Scott says:

    So much goodness in this post!! Especially love your thoughts on how to stand out when you’re just starting out and negotiating!

  3. Shannon says:

    You look so good in red. You should wear it more!

  4. Melanie says:

    That black blazer outfit is chic AF! Love it!

  5. Sharni says:

    SO much incredible advice! I especially love the tip of having a Job Well Done folder in your email! There are so many days where I have a little bit of a wobble in the self-confidence arena, so this will help me out so much.

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