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How to Make Tough Choices You Might Face at Work

Find answers to some thorny questions you could see on the job

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Ryan Johnson

En español

I’ve just been passed over for promotion for the second time — again to someone 20 years younger than me. Should I make a stink about age discrimination or move on?

There’s a much better option: Build a case for why you should be considered for a promotion, and present it to your boss in a calm, professional manner, says Jim Peacock, principal and founder of Peak Careers Consulting in Waterville, Maine. “You definitely don’t want to go in with boxing gloves on. There’s no way you can win that way.”

To prepare, make a list of at least five ways you add value to your organization, each with an example of its impact, Peacock advises. If, say, one strength is that you are highly organized, cite how your systems keep the workplace running smoothly. If you have strong interpersonal skills, reference how you attracted new business, resolved conflicts with customers or serve as an unofficial mentor.

In creating the list, consider assumptions your boss may have about you so you can counter them. “Your boss might have age biases buried deep and not even realize it,” Peacock says, adding that common assumptions are that older workers won’t be on the job longer and aren’t great at adapting to new technology.

Hit on each assumption with a positive twist, Peacock says. “You might say, ‘I am always eager to improve my technology skills. I’ve never shied away from learning and staying up with new software or systems.’ Or, ‘I’ve loved working for this company and plan on working for another 10 or 20 years.’ ”

Don’t underplay any of your strengths. You might assume they are obvious, but they are often not, especially if your boss oversees a large group or has broad responsibilities, Peacock says.

After presenting your case, ask your employer for input, he says. “Say, ‘I am concerned I’m being overlooked for advancement. What can I do?’ ”

If you continue to be overlooked and truly believe age is a factor, only then should you consider booking an appointment with your human resources department.


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Ryan Johnson

I’ve gotten a great job offer, but it’s 300 miles away and I can’t work remotely. Should I quit my current job and uproot my household in order to take it?

It’s easy to get overwhelmed by a decision like this, which affects not just your career but you and your family’s entire life. Rebecca Michel, an associate professor in the counseling program at DePaul University in Chicago, recommends a decision-making ladder that begins with your values and ends with your preferences.

On the first rung, detail all financial benefits or drawbacks of relocating, beyond just the obvious salary and benefit details, Michel says. Are housing costs higher or lower in the new location? Would your spouse or partner have to find a new job and lose income during the job search? Would you have to budget for more commuting expenses? Are there advancement opportunities at the new company?


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Next, consider your family’s circumstances. “If you’re in the sandwich generation helping both parents and young children, this gets more complicated,” Michel says. The implications of moving — finding caregivers, changing schools, switching doctors and health coverage — can be dealbreakers.

The next step is to evaluate your preferences for location and community, and how comfortable you are with big changes. “If you are part of a faith community or civic organization, investigate if there are similar options in the new location,” Michel says. “Weigh the impact of disruption — some people see it as an adventure, but others struggle with it.” Still unsure? You may need more information to make a decision. Ask to meet with your future colleagues. “A big unknown is often the people you’ll be working with,” Michel says. “You want to be sure you like them.” If you aren’t clear on certain aspects of the job offer, request a call with the human resources department.

Remember, you’re in a sweet spot. With both a job and an offer in hand, you have leverage to ask your current employer for a raise and even a promotion, and to negotiate a sweeter deal from the prospective employer.


a man leaping over his work desk and out of his cubicle to freedom

Ryan Johnson

I’ve gotten tired of going through the same daily grind with the same people for a large organization I can’t really influence. I've been thinking that I'd be happier if I left the corporate world and went freelance. Is this the right move? 

It’s possible that the pandemic has given you a taste of what freelancing could be like — a flexible schedule, no dress code, a pet-friendly office and maybe the freedom to pick and choose projects.

“But there’s a danger in romanticizing the freelance life; there are plenty of potential drawbacks,” says Sharon Givens, a psychotherapist and founder of Visions Counseling & Career Center in Columbia, South Carolina. She suggests you tackle the question by considering the following factors.

Finances. It’s often not enough to match your current salary, because your expenses as a contractor can be significantly higher. “If you have to pay for your own medical insurance, any travel expenses, upgrade your home office — these are significant costs you have to budget for,” Givens says. Plus, your taxes often go up, now that you don’t have an employer paying half your Social Security taxes.

What’s more, freelance income can be highly irregular, so you’ll need to have a cushion of at least a few months’ expenses.

Clients. Who will hire you? For a comfortable freelance life, a broad network is critical, so you should have that in place before you take the plunge. You’re probably not ready if you have only one or two potential sources of work. Aim to secure a contract before leaving your corporate job.

Responsibilities. Freelancing means not only performing your typical professional role, but also taking on new duties, such as marketing and accounting. And when your computer acts up or you need to set up a web or social media site, a corporate IT staff isn’t going to swoop in and help you out. These additional tasks can cost you time, money, peace of mind — or maybe all three.

Lifestyle. As a freelancer, you’re usually a team of one. “You have to really know yourself and what drives you. If you are motivated by sharing goals with colleagues and having that social interaction throughout the work day, freelancing may not be the right choice,” Givens says. “It can feel very isolating.”

Karen Hube is a veteran financial writer and a contributing editor for Barron’s.