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How To Talk To Your Kids About Career Choices


In this season of life I have two high schoolers that are thinking about their first jobs and college majors. They’re experiencing the rush of earning their own money, making choices about how they invest their time and what they want their future lives to look like. Call me a masochist, but it might be my favorite parenting moment! And probably the reason I’m a recruiter. 

So, in the spirit of back to school, this post is about first [high school] jobs and college majors: How to talk your kids off a ledge and remind them of all the opportunities in front of them.

First Jobs

Teach The Process 

As parents, we want to curate an amazing entry into the work world for our children. We fantasize about meaningful internships and apprenticeships that prompt them to discover new interests. Meanwhile, they’re just hoping to earn some spending money and work with their friends. When they come to us for guidance, it’s easy to overstep and get the job for them rather than teach the process. You have the opportunity to shape foundational skills that will serve them for the rest of their lives. As the adage goes, “Give a man a fish…”

I had our high school daughter put together a resume, including her camp counselor and babysitting experiences. (ChatGPT is helpful here.) We talked about the places she wanted to apply and what skills would be meaningful to those employers. She collected references. We rehearsed typical interview questions. I encouraged her to research the companies’ websites to formulate her own questions and talking points. 

Here’s what important about the process:

  1. Resume – Learning how to present themselves to the world
  2. Applying & Following Up – Disabuse your kids of the notion that it’s rude to follow-up
  3. Interviewing – Address the employer’s needs before talking about your own
  4. Balance of Wants vs. Responsibilities – Appreciation of what it takes to run a business + reliability; Recognizing what’s fair vs. opportunistic
  5. Work Ethic & Team Dynamics – How to deal with varying levels of contribution
  6. Negotiation & Advocacy – Effective conversations about their needs
  7. Openness to Learning – Asking for help and receiving criticism

Life Skills

While high school jobs and internships can inform future career paths, they also teach important life skills: Flexibility, teamwork, prioritization, ownership, accountability, hard work… and importantly, not to cut the avocados too early because they’ll brown. 

Chris Sacca, venture investor and founder of Lowercase Capital and Lowercarbon Capital, famously writes about sweet and sour summers. As he explains on The Tim Ferriss Show, his parents would organize a sweet job (high-powered internship) and a sour job (any of Mike Rowe’s dirty jobs would qualify). One summer he interned as a lobbyist, followed immediately by a job in construction. The idea was to expose him to different environments and people: Sometimes personal development and critical thinking were the focus, other times you just needed to push something heavy uphill. 

When Sacca does his own hiring, he looks for experiences that taught humility, whether it was a dirty job or time spent abroad in a non-English speaking country. “Humility comes from needing to ask for help. The best managers in the world are great about asking for help.”

Also, everyone should wait tables. 

College Majors

A recent school assignment had our high schoolers asking: 

Knowing what you know now, what would you have done differently [academically]?

Do you have any regrets about your choices?

My regret is latching onto a career path early in college. (I did a full-time marketing co-op the first semester of my sophomore year). Then taking a myopic focus and leaping into work right away. In other words, I specialized too early and didn’t take the time to sample other classes or professions.

But specializing early is what’s being evangelized right now. As we wrote about in The Checklist Manifesto post, technology and innovation have allowed us to solve problems more complex than any one brain can master. The sheer volume of knowledge has required us to specialize. The role of the general practitioner is going away.

As a result, high school students have access to sophisticated course offerings, apprenticeships, and classes for college credit. Getting ahead in a certain discipline and pursuing universities known for those disciplines are ways to stand out in the competitive college application process.  

The tricky part is that for every 1 student that knows they want to be a pilot or a software developer, there are 5 that are talking to me about a career change in their late 20s. They specialize early, conceivably to get ahead in their field, only to discover later that they’re unhappy with the profession they’ve chosen. 

There’s a remedy for this: 

  1. Sample before you specialize
  2. Experience your career path IRL

Embrace The Buffet

I was certain that I wanted to be in International Relations or Journalism until my freshman Current Events class when I realized I didn’t love reading the newspaper! So I went for a “practical” business degree, but never explored HR, organizational management, or took a creative writing class for the heck of it. (To be fair, I don’t think entrepreneurship was a thing back then!) College is the most convenient time to explore. It’s harder to make room for interests or upskilling later. 

Take It For A Test Drive

Career aptitude assessments and strengthsfinder tests have come a long way, but are strikingly void of lifestyle questions such as: Do you excel in corporate environments or entrepreneurial ventures? Do you follow a maker’s or manager’s schedule? Are you an individual contributor or team player? Do you prioritize creativity or altruism over earning potential? Do you want to travel? Have summers off? Are you a risk-taker or prefer security and predictability? Can you deal with variable income or a “busy season”? 

Without getting real-life experience in your work environment, you’re missing the connection between career and lifestyle. 

In Conclusion

The central theme here is to take advantage of all learning opportunities. Have your kids do the sweet and sour summers. Experiment with classes they’re curious about, even if outside their perceived career path. Be intentional about their internship choices, using them to evaluate work environment, earnings potential and lifestyle.   

A few resources:

Xello: Help students build 21st century skills

Truity Career Personality Profile

Steele St. College Consulting Resources

Comments please. Did you give your kids career advice and live to tell about it? Please share so we can all benefit.

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