An Expert Tells You How to Turn Your Career Challenges Into Opportunities

Cali Williams Yost, founder and CEO of the Flex+Strategy Group, on how extraordinary women can make pivots in their work and life.

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Even though today's work and life reality is more flexible than you think, managing our day-to-day in a 24/7 economy can still be a challenge. As the founder of Flex+Strategy Group, a growing business that helps create a flexible work culture for clients, and as a woman with two kids and a husband, I face the same array of seemingly endless choices many other women encounter: Where and when do I finish this presentation most productively? When will I be able to attend one of my daughter's field-hockey games? When can I get a haircut? Then there are bigger life transitions, like the pregnancy that caused one of my clients, a rising star at an investment bank who loved her job, to question her ability to have a career and a family. But the truth is, whether we work in an office or remotely, full-time or on a project basis, in-person or online, creatively rethinking how, when, and where we get our jobs done can offer countless opportunities for extraordinary women to turn what can feel like obstacles into triumphs.

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First, we have to rid ourselves of the limiting, all-or-nothing mind-set that says it's either "this or that." There are many ways for you to earn money and manage your life throughout your career. It begins by recognizing that each of us has a different set of circumstances at any given time — there is no one right way to do it, except to keep learning and adapting as we go.

For me and for my clients, that recalibration of how work and life fit together can simply happen week to week. Even a bigger reset, like the one I guided the aforementioned banker through, might have an outcome that surprises you. As she was expecting her third child, she presented a plan to work four days a week, one of those days remotely. I wasn't surprised when her manager agreed, but she was. Today, this woman has three happy, healthy children and is a C-suite leader of the U.S. division of a global bank. When I see her, she will often say, "I can't believe I almost walked away."

Here, I answer Lenny readers' questions about how to live and work with strategic intention so you, too, can be your best self at work and at play.

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Q: I've been out of college and working since 1993 in the same job: print-media sales. Four years ago, I quit my job of nineteen years to alter my career path. I'm willing to start at the bottom and take a pay cut to make this shift, but I don't know how to get someone to take a chance on me. How do I start over at 47 when most companies want to hire twentysomethings?

Cali Williams Yost: Let's start with your belief that companies are hiring only millennials. It's common when we have to make a big change that we get in a false narrative, that you think one thing when the reality is something different. In this case, you've convinced yourself that companies are hiring only millennials, which then infers they are not hiring you because you're 47. Yes, companies are hiring millennials — they have something to bring to the table. But somebody who has nineteen years of experience is also valuable to an organization.

The key question any company wants answered is: How can you help me get this job done well? You have to take a step back and say, "What is it that I'm bringing to the table?" Now, you don't want to be in print-media sales, but every single organization has to sell. Selling is an art and a science — it's not easy. You could go in and say, "Hey, I want to get into this new industry. Let me bring my sales understanding to the table to help your business thrive." You could start on a project basis and make a little bit of money, show your value, see if you like them.

It's so important to tell your story across your network. I did this myself. I was 30 when I made the transition from banker into a work-life-flexibility consultant. I looked at my background and I tried to see how I could add value to the two organizations in the whole country that were doing this work at that time. I was able to show one of these entities that I could help them with a client they'd just taken on, which was a bank. So they took a chance on me; they let me have an internship. If you're willing to say, "Look, I'll start from the beginning. I will take a pay cut," that gives them wiggle room to say, "All right, we'll take a chance on you."

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Q: Four years ago, I left my career in luxury cosmetics to follow my husband to another country. I didn't work for two years when I had my first child. Then I started a jewelry company, but after two years, my cofounder and I decided it was far from profitable and stopped business. Now I'm a receptionist. How do I turn this detour into something positive for future employers?

Cali Williams Yost: This is something that I find very interesting with people who have taken different career paths: You actually didn't take a career break, you worked for yourself. It's the craziest mentality: "If I'm not getting a paycheck from somebody, I'm not working." You were an entrepreneur. That would be a great example of a pivot into a different type of flexible work and life reality.

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So how do you expand your skill sets so you're even more valuable the next time you pivot and you go on to the next job that you want? As a receptionist, you are in a customer-service role, and many organizations have client-relationship management systems, like Hubspot or Salesforce — learn that, offer to be one of the people who contribute to maintaining that. You can also be somebody who monitors social media. Say, "Look, it's like people are walking into the front door of our organization when they go on Twitter or Facebook. I want to keep track of what people are saying." They will value that information, and it allows you to learn these systems, which you can then use in your next job.

Q: I'm 28-year-old architect but have been studying at a culinary academy for almost a year. I've found myself stuck between my salaried job, where I'm not progressing, and my desire to make my own path as a business entrepreneur and pastry chef. How do I turn my side hustle into a career that supports me?

Cali Williams Yost: You don't have to make some dramatic decision to cut off your sole source of income to take a risk on this new career; you actually can do it in a slow transition that allows you to keep the income of your current job but also move into this new career in a staggered way.

I would imagine that you could potentially stay full time as an architect but start to do some of these culinary activities on the weekends and in the evenings. You could connect with somebody who is doing weddings; maybe a restaurant needs a second sous chef if they're short on the weekends when they're busier. As that maybe heats up, maybe you get more hours at the restaurant, or maybe you start catering more during the week.

This is where you go to your architecture firm and say to them, "I would like some more flexibility and to work fewer hours. Here's a plan for how this is a win-win for everyone." You may have to take a pay cut. You may have to go on a project basis. You may lose your benefits, but you still have that income that's going to help you make this next stage of the transition. You've pivoted as you need to build this other side of your life to where it can be self-sustaining.

Q: How do you prevent burnout? And how do you deal with it when you realize you're already burned out?

Cali Williams Yost: Burnout is the 21st-century challenge that we do not talk enough about. The first thing you need to do is understand what your signs of burnout look like, because not everybody's are the same. For me, for example, all of a sudden, things just start to get really hard — the thing that used to take you two minutes to do now all of a sudden takes 45 minutes. When that starts happening, the first thing I do is say, "What are some small activities or actions that I could put back into my work-life fit that may actually make me feel good?"

Typically when I've gotten into this place, I've started ignoring the things that actually fill me up, that make me feel really good. That could be something as simple as, "OK, I'm going to leave half an hour earlier, and I'm just going to go for a walk with my friend. Or I'm going to make sure I make a dinner date with my husband for the weekend. Or I'm going to sit down and spend some time with my daughter, because I've gotten so busy that I haven't even connected with her." It's about understanding the things that give me perspective again and help me reconnect with myself.

This is where you could begin to leverage this flexibility that more and more of us have but that we don't tend to thoughtfully use. You could say, "I actually can work remotely in my job. Maybe what I could do is think about the tasks that require a lot of thought and I have a hard time finishing when I'm in the office." So do those tasks like a report or a data analysis when you're working remotely and save yourself the commute.

You really have to think about how you're working and where you're working. That's when you start to say, "I think I am going to go to my kid's play" or "I am going to go to the gym." All of a sudden, you start to be efficient with your work, but you're also rebuilding these other things into your life that really do make you your best self.

Cali Williams Yost is a noted workplace strategist, researcher, author, speaker, and the founder of the Flex+Strategy Group/Work+Life Fit Inc.

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