To succeed in your career, play it like a game, career coach explains in new book

In her new book “Secrets of the Career Game: 36 Simple Strategies to Win in the Workplace,” career coach Kendall Berg reveals a range of strategies for taking control of our careers that combine pushing for bigger promotions, titles, and paychecks, but also finding work that fulfills.

Her take has sparked more than half a million followers across Instagram, TikTok, and YouTube who are trying to get ahead at work and be happy.

I asked Berg to share some insights. Here are edited excerpts of our conversation.

Kerry Hannon: What’s the key to success in the career game?

Kendall Berg: It’s choosing intentionally and strategically where you want to play the game, how you want to play, and when to not play the game. There are times in our career when it might be more beneficial to do something for our progression, but it crosses a value line that we have, or a boundary that we have.

How is a career a game?

It’s a lot like chess, where there are moves and counter moves, rules and no rules. When my husband and I first got married, he decided to teach me to play chess. He conveniently left out a lot of the rules that would’ve helped me win.

Your career operates similarly, where there are some rules that you’re told: Here’s your job description. Here are the expectations for you to be successful. Here are the deliverables. Here are your deadlines.

But there’s a whole other set of rules that you only learn by playing, which is not how hard you work. It’s who you are building relationships with, how you advocate for yourself, how you talk about the work you do.

If you take the first job offer that you get every time you are searching, regardless of how it matches your passions, skills, or values, the only person who gets held back is you. If you stay loyal to a company that doesn’t promote you or give you opportunities for growth, the only person who ends up stuck is you.

There’s one crucial rule that’s common to both chess and the career game: Even when you start off as a pawn, it’s possible to become the queen — the most valuable piece on the board.

You write that career progression rarely depends on merit all by itself. Elaborate on that.

Most of us think that our careers are going to be a straight meritocracy. We’re going to go to work, do our tasks, and that alone is going to be enough for us to get promoted.

But it’s not true. Progressing in your career is not about the merit of doing your core job, it’s about developing the right soft skills to be an effective leader.

We have tunnel vision. I see it all the time: Individuals who are working hard on a million different projects, increasing their mental load and stress levels exponentially, only for their leadership to be blissfully unaware.

Even if your boss is paying attention, odds are they don’t have time to understand the intricacies of the work you’re doing, the level of detail, the collaboration that it requires, the amount of time that it requires.

So if you’re not advocating for yourself, sharing all of those details, communicating the value of the work you’re doing, they’re not going to have a case to promote you. That’s why a lot of people get stuck. Maybe you’re capable of operating at the next level, but you’re not talking about it.

Why should we run our career like our own business?

If I run my career like a business, then I’m thinking like a CEO. I’m thinking, do I want to take this client on— which is the company you choose to work for versus feeling desperate to be employed by a client.

I’m constantly selling myself and my business. Here’s what I’m good at. Here’s the value it brings your company. Here’s why it’s important. I’m thinking about the impact that my business has. Anybody who’s been a solo entrepreneur, started a side hustle or a business, knows you’re in sales 99% of the time. You’re out there saying, here’s the value of the work I’m bringing. Here’s the impact it has on your bottom line.

When you start to shift into a CEO mindset, you’re constantly building relationships so that your business can grow, so that you have more opportunities in the future. Otherwise, you’re just a cog in the machine who’s taking a salary. You’re not going to see that same upward mobility and trajectory that you may want.

Kendall, you write about the importance of self-development, let’s discuss.

When we hit 40, our self-development basically craters. We start to get to this mindset where we think we know everything. I’ve been doing this for 20 years. I’ve seen a thing or two,

The reality is our landscapes are constantly changing. If you’re not investing in yourself, if you’re not learning AI, new technologies, there is somebody who is, and that person is going to get the promotion.

What’s your list of 11?

The 11 list is a homegrown tool that I’ve built over the last eight years of coaching that is intended to help you understand who you are and how you want to show up at work.

It’s five things you want to be known for at work, five things you don’t want to be known for at work, and one personal brand statement.

We’re really hard on ourselves. And having a rubric of self-evaluation can help us really measure a good day versus a bad day. It helps us to see if we are growing in the direction we want to be known for at work, or are we starting to slip into bad habits the way we don’t want to be known for. Once you understand yourself as you are, not as you would like to be, you can begin to better articulate the value that you bring to your team.

Have a question about retirement? Personal finances? Anything career-related? Click here to drop Kerry Hannon a note.

What advice would you give someone who has recently been laid off?

Getting laid off sucks. There are a lot of emotions that go into being laid off that make you feel really uncomfortable, really unvalued. They can be very detrimental to your confidence. You feel it’s a setback. It’s an emotional grieving process post-layoff.

You have to give yourself time and space to feel those things, but not too much. You’ve got two weeks. Feel all your feelings. Cry it out, if that’s your personality type. Go to Aruba.

Sit with it, then you’ve got to get back in the game relatively quickly.

Meet with anybody and everybody who you’ve ever worked with, who you liked, or who works at a company that you like. These can be in person or virtual for 15 minutes to catch up, but in person is better. These are not “can you please refer me” calls.

Then write down your 11 list, your passion statements, your personal brand statement, and start to identify jobs you want to target.

Your personal brand is going to be how you talk about yourself in interviews, how you talk about yourself on your resume, how you talk about yourself in a coffee chat.

Start applying for jobs only after investing in warming up your network, creating that right resume, creating that right story, creating that right passion question assessment

Then go out to the job marketplace. It could take three to nine months to get hired, but be intentional and connect with people because most jobs are being filled by referrals.

Kerry Hannon is a Senior Columnist at Yahoo Finance. She is a career and retirement strategist and the author of 14 books, including the forthcoming “Retirement Bites: A Gen X Guide to Securing Your Financial Future,” “In Control at 50+: How to Succeed in the New World of Work” and “Never Too Old to Get Rich.” Follow her on Bluesky.

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