The Professional Generation Gap

How do you advise your kids on their careers when you’re still figuring out your own? Get an expert’s tips on some of the perennials of career planning that any concerned parent can cleave to.

My sister-in-law has just graduated, from a good college with a good degree, and has started looking for a job. She’s a lot younger than I am and it’s been a very a long time (and three careers) since I stood in her shoes. But I can still remember the panic and the excitement of being, for the first time, free of an institution and a timetable, confronting the dreaded question: what am I going to do with my life?


She’s getting a lot of advice from her parents. And it’s been fascinating to watch. Because, as retirees, they’re a long way now from the job market. And their experience of the work world is decades out of date. Watching the discussions and arguments whirl around me has made me realize just how much work has changed and how hard it is to give anyone advice that isn’t obsolete.

What do Kim’s parents want? They want her to get a good job with a solid company that will leave her (eventually) with a good retirement plan.

What does Kim want? Kim wants to make some decent money so she can live decently for a change. (She was a thrifty student but economizing is starting to pall.) She wants to find out if her talent for art could lead her anywhere. She wants to work with fun people and to do something that isn’t mind-blowingly boring. She isn’t oblivious to money but right now retirement is pretty far from her mind.

There’s not much common ground between them. Why? Because Kim is living in the present and her parents are living in the past. As a parent myself, watching their mutual incomprehension has given me a lot of food for thought about how any parent stays abreast of the modern workplace and how we advise our kids. It’s baffling evaluating entry-level positions once you’ve escaped them. It’s hard to advise on salaries and opportunities. However much you may read and discuss the modern workplace, the chances are that, as parents, we are out of touch.

So what are the perennials of career planning that parents can cleave to?

Start with great companies, not great jobs: It’s a highly unusual graduate who walks into a great job. However expensive that education was, it rarely equips anyone for serious responsibility inside a commercial organization. So entry-level positions are, almost always, lousy jobs. All they can offer is two things: the opportunity to shine, and the reflected glory of the company name. Any first job has to have at least one of these; if it has both, you should be proud of your child and show it. If it has neither, it may pay the rent but it’s a waste of time. Buy your child a big dinner and urge him or her to keep looking.


Don’t look outside; look inside: Successful careers require knowing what you want and how to get it. But without a lot of experience, how can your child know either of these things? Quite a lot as it turns out. Instead of talking to her about retirement plans, it might be more useful for Kim’s parents to discuss things she’s done — exams, jobs, projects — and ask some good questions. What was satisfying about them? Did she prefer challenges that involved other people or where she could be independent? How much stretch and stress did she enjoy? Does she like speed and time pressure? How competitive is she? Put an uncompetitive person into certain industries and they’ll die; put a competitive person into a place that doesn’t stretch them and they’ll be universally loathed. Everyone loves to talk about themselves. These conversations with your kids may be some of the most reflective and rewarding you’ll ever have. But remember: your job is just to ask the questions.

Experiment: Every parent wants to see their kids settled. Some of this is selfish — we really would pay money to be able to stop worrying — and some of it is protectiveness: we want to see a company value our offspring appropriately. But the truth is that very few kids really know what they want to do when they graduate. And the only way to find out is to try things. This can be nerve-wracking for parents. One day he’s working in retail and the next day thinking about medical school? Is he a genius, a schizophrenic or just flaky? Don’t be too impatient. I tried trying banking, retail, commodities trading and psychology before settling into a thirteen-year broadcasting career. I don’t regret any of those experiments, because they taught me the difference between the environments in which I thrived and those in which I withered. How else could I find out?

Talk about money: Unless they come from very poor backgrounds, most kids under-estimate the importance of money. They want — quite rightly — to pursue passions and dreams. I think that’s great and I always encourage it. But I also know that some dreams will never pay well and won’t suit a hedonist. In these conversations, money needs to be neutral: what is important is that expectations goals match financial tastes.

Start and finish with values: Whatever values your kids hold (and you may not share them) aligning personal values with values articulated at work is, in my opinion, the single most important aspect of a satisfying career. If your children want to change the world, don’t let them join a conservative institution. If they love order and routine, steer them away from start ups. If they’re independent free thinkers, don’t send them into a law office. If they need to feel they’re making the world a better place, don’t put them in retail. It isn’t about good and bad industries; it is about fit.

Make a plan: When your children have a sense of what they want to do, encourage them to make a plan. Who do they know who can help? Where are the key information sources? Do they have the skills they need and, if not, how will they acquire them? Marjorie Scardino, the CEO of Pearson, says you should have a plan and “execute it violently.” She points out that we plan most major aspects of our lives — weddings, vacations, house moves. Why not plan a career? Opportunism is great but unreliable. Plans have a weird habit of illuminating opportunities — but when those don’t come along, you still have momentum.

The reason Kim and her parents are at such loggerheads is because they started talking about jobs and industries first. But jobs and industries change. What matters to anyone at any stage of their career is understanding who he is and what he wants. That will keep changing. But if your children know how to explore those existential questions, you will have given them the career tool that will never date.