How to successfully navigate all of life’s milestones

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Maaaan, life is hard. It's so unpredictable.

Just when you think you have it figured out, you're thrown a curveball and whiff. Badly.

In baseball, you get more at-bats. You start seeing more curveballs and you get better at hitting them.

Life isn't that much different. What if I told you it's not that unpredictable. It only looks unpredictable.

Life can seem hard and unpredictable, but I'll tell you how to successfully navigate life's milestones -- and the answer may surprise you!Many of life's problems already have solutions. What worked three hundred years ago, often still works today. The tools might be slightly different and the situations might be slightly different, but they're pretty much the same. The ball might curve a little differently but, fundamentally, a curve is a curve.

That's why you see all those “things I should've done in my 20s” or “why millennials are…” articles. One of the tricky things about writing for an audience greater than one is that you are often pushed to make generalizations. We see it all the time in mainstream media. (oh and those “Generation whatever is the reason we're all in some kind of mess — just throw those in the trash)

Despite the passing years, many of our challenges remain the same. How do I get a job? How do I find a mate or get my family off my back about not wanting a mate? How will I get a raise? How will I retire? How will I start a family or get my own family off my back about not wanting to start a family?

As individuals, it's more effective to think in life cycles and milestones, not in ages or generational cohorts (GenX, Millenials, GenY, blah blah).

There are a handful of milestones that most people will experience – marriage, divorce, starting a family, first job, getting fired, second job, retirement, death, etc.

Not everyone will experience every life event but at each major milestone, you and your thinking will shift a little. You need to draw more knowledge from someone who has navigated the event already, less from someone who happens to be closer in age. That's how you overcome those challenges successfully.

If you want to successfully navigate all of life's milestones, the answer isn't in asking people your own age or reading articles for people your own age.

On average, a 30-year-old woman who is expecting a child will have more to learn from a 45-year-old woman with kids than another 30 year old who isn't expecting or have kids. It could be on big issues, like “how do you balance kids versus career?,” or small ones, like “what do for childcare during teacher in-service days?”

The 15 year age difference is less significant than the milestone of having and raising children.

The different “generations,” which are themselves artificially created anyway, are even less important. The 30-year-old will face the same issues the 40-year-old may have faced and will draw inspiration and knowledge from her.

When you have a problem, do you look to someone in your generation?

Or to someone who has faced those issues before?

If you're wise, the latter. πŸ™‚

The internet is fantastic for this type of research because people are sharing their experiences every single day. If you have an interview with Google, Microsoft, and Amazon – you can search through hundreds of stories to get a better idea of what to expect.

If you're just looking for an internship or looking for better mental models of how to get a job, you can find hundreds of experts who have distilled their experiences working with thousands of individuals. Through one person you can get the best of the best from the experiences of thousands — how awesome is that? It's freaking unbelievable. (if this describes you, you need to read Ramit Sethi's Briefcase Technique AND his Truffle Principle — it will fundamentally change your mental models about hiring)

Remember, all this has happened before, and all of it will happen again. Don't make other people's mistakes twice. πŸ™‚

After I wrote this post, I stumbled onto an episode of Hidden Brain in which Shankar Vedantam and Dan Gilbert talk about how we're horrible at predicting the future. One of the solutions is to ask someone who has already experienced something to share their impressions, like about a movie or a date. This is exactly what I mean about speaking to someone who “navigated the event already,” vs. someone closer in age.

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Jim Wang

About Jim Wang

Jim Wang is a thirty-something father of three who is a frequent contributor to Forbes and Vanguard's Blog. He has also been fortunate to have appeared in the New York Times, Baltimore Sun, Entrepreneur, and Marketplace Money.

Jim has a B.S. in Computer Science and Economics from Carnegie Mellon University, an M.S. in Information Technology - Software Engineering from Carnegie Mellon University, as well as a Masters in Business Administration from Johns Hopkins University. His approach to personal finance is that of an engineer, breaking down complex subjects into bite-sized easily understood concepts that you can use in your daily life.

One of his favorite tools (here's my treasure chest of tools,, everything I use) is Personal Capital, which enables him to manage his finances in just 15-minutes each month. They also offer financial planning, such as a Retirement Planning Tool that can tell you if you're on track to retire when you want. It's free.

He is also diversifying his investment portfolio by adding a little bit of real estate. But not rental homes, because he doesn't want a second job, it's diversified small investments in a few commercial properties and a farm in Illinois via AcreTrader.

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  1. Kalie @ Pretend to Be Poor says

    When I was expecting our first child, I was so excited to become a parent but also so terrified. I knew I wouldn’t know what to do for lots of scenarios that would happen over the years. I remember being to comforted by the fact that I have older friends who have been through this, as well as my own mother who raised five kids. I don’t know if inter-generational friendships are common, but I’m very grateful to have them!

    • Jim Wang says

      Yes! Having a few friends who are even just a couple months ahead of you can really calm the nerves. I remember when our son bit his lip and there was blood everywhere, we were kinda of freaking out. Fortunately, a friend of ours said – “give him an ice cube” and he happily sucked away on it until the bleeding stopped. No big deal. Looking back, it’s funny we were so frightened. πŸ™‚

  2. The Vigilante says

    “As individuals, it’s more effective to think in life cycles and milestones, not in ages or generational cohorts (GenX, Millenials, GenY, blah blah).”

    I was only vaguely aware of this blog before I read your recent comment on the Rockstar forums and the above quote. Now that I’ve seen a bit more of your writing and the thought you put behind each sentence, I feel like I’ve been missing out! You have a big new fan, sir.

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