Have you Been Strategic about Career and Money

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A couple of recent mainstream articles really got me thinking about the early part of my career and money. Our struggles with debt show we were not very strategic when it came to thinking about our money, but what about careers.

I’m not sure if I ever had a calculated plan beyond heading to college and wanted to land a steady, well-paying job. I had no precise definition of what well-paying was, just enough to support my needs.

My parents had laid the groundwork for a good work ethic. My dad always worked. Over time, part-time jobs, and side jobs too over the years to bring in extra money, and my mom after raising five children returned to work once I the youngest was in school.


Even with no real strategic plan, other than working hard, I’ve still managed to earn a six-figure income. I’m not sure if that was a blessing or a curse given the mismanagement of that money for years. Would less of an income mean less failure or more, would a larger income mean we would have gone into even more debt?

I’m not here to second guess myself or speculate on what might have been. I’m all about moving forward these days. It does, however, make me wonder how to make these lessons valuable to my three children, and improve upon the things I was taught, and have them learn from my failures.

Critical Thinking

When I look at charts or read articles that cover topics on how much money you should be saving during specific periods of your life, they make sense to me. I mean as a guy in his mid-forties, who over the last several years cleaned up his finances, they better.

For example, this how much money you make and spend in a lifetime chart from a recent Business Insider article, compiled with data from a Consumer Expenditure Survey.

I get it your career and earnings have a trajectory, it’s not linear, and it should be upwards. I’m a little surprised at the decline in the early 50s. I would at least expect that to be flat unless you stop working altogether.

Looking at the above automatic millionaire savings chart, again pretty straight forward they earlier you start saving, the easier it is to amass wealth, and the later, the more work you need to do.

Now how to bundle my years of experience, my money history, career knowledge into a meaningful way for my three children to look at the same information now, and get excited about it.

Well, honestly, I’m not 100% sure, but I believe it starts with critical thinking — the ability to objectively analysis and evaluation of an issue or information to form a judgment.

If my kids can do that inevitably, they can see that saving money early and often will be useful, no great for their futures. The key is getting them out of the routines they have been in for years.

Critical thinking is not the memorizing of facts that you can learn once and then use forever, such as the multiplication tables, its way of thinking about particular things in a specific time

Break The Cycle

Now more than ever, parents need to be active partners with their school districts and vice verse. We both have something to offer.

For those parents lacking the tools to help their children in certain areas, the school system can offer assistance. Parents and the community as a whole can provide valuable real-world feedback and experience to help improve the quality of the education being taught.

This all requires changes, breaking the regurgitation of facts and memorization of tables, and teaching better real-world skills like:

  • technology
  • financial literacy
  • interpersonal communication
  • critical thinking
  • teamwork
  • career readiness

I’m really beginning to envy homeschoolers. Given a broader base of real-world skills students, our children will be less likely to follow in someone’s footsteps, because they will be able to make a path of their own. They will have the strategic ability to plot the course and critically think about the outcome.

Sure I just dumped a ton of other stuff on our already overload children’s lives, but I’m pretty sure they can handle it. I believe it will relieve the mindless homework cry I have heard 100 times before in our household “when will I ever use this in my life.” The above skills will be carried for a lifetime, and take them much further than memorizing some textbook facts.

Have you ever been strategic about your career or money? What’s the best way to teach kids what you know now about careers and money?

18 thoughts on “Have you Been Strategic about Career and Money”

  1. I’m trying to answer that question everyday.. how can I be strategic? I don’t know – I feel any move to a more lucrative role or switching teams is a little bit backstabbing in a way. It’s important to keep getting solid bumps each year and then move when you see negatives to staying.

    For kids, I don’t know either. I’m trying to figure out how to influence my sisters.

    • It much more common nowadays to move more frequently. I think it’s okay as long as you are not chasing the money and burning bridges.

  2. Hmm, good question. I don’t think I’ve been as strategic with my career as I could have been. I’ve been guilty of job hopping instead of sticking it out at a company, which is definitely a weakness of mine.

    • I don’t think job hopping is necessarily bad if you are doing it for good reasons. Companies will not be loyal to you if they need to make cuts.

  3. We’re still early days in school, so the answer to “When Will I use this?” is still “Every darn day. Everything builds on this,” rather than “You may not. Some of your classmates, though, might, depending on their career path. And you never know where your career path will take you.”

    I would never have thought my career path would lead to banking, accounting, and tax preparation. Teenaged me would have thought it was boring and not areas that clicked with my analytical bent.

    My parents talked about jobs, not careers, but my mom drifted through several disparate ones (teaching, commercial art, sales, social work) and my dad always knew he wanted to practice law…in his dad’s firm. I think Jon and I may be far more explicit with Little Bit about career paths, job dos and don’ts and networking. I know we’ve already been more explicit about money.

    • Sounds like Little Bit is getting a great foundation. The early years of school are building blocks, but we have found the high school years can be numbing for some students if they are interested in other areas.

      It is tough for teenagers to really have a focus on where they’ll be in 5 or 10 years. I still believe it’s valuable to have them information planted in the back of their heads for use when they are ready.

  4. I kind of fell into my retail career, but once I was there I was fairly strategic about it until I started changing careers. I never really found that mix of something I was passionate about and something that earned good money. Unfortunately, my kids didn’t get many important takeaways about my working life, and they both seem to be casting about rather than strategic in that area.

    • That’s a big key Gary, finding something you’re passionate about or at least have a good work/life balance with decent income. If not you become one of those dreading Mondays, always hoping for Fridays type of people.

  5. I can’t say I have really seen that automatic millionaire chart before, although I know I periodically read an article and it inspires me to keep picking up the occasional penny I see in a parking lot.

    Your point on critical thinking also nailed it on the head. It’s something we want to teach our children because technology has made so we don’t have to solve problems. My wife and I were talking last week how we even use the iPhone calculator to do simple math that did in our heads a few years ago.

    We have also read articles how employers are looking for applicants that can think for themselves instead of needing to be told every move to make.

    • Thanks for your comment Josh. Independent thinkers, employees who don’t have to be micro managed every minute of the day sounds great! I know as a managing that the team I’d like to lead.

  6. I just started reading a parenting book called “How To Raise an Adult.” The premise is that in the past, most children were raised with a clear goal in mind. If your father was a blacksmith, you were raised to be a blacksmith. If your family were farmers, or aristocrats, you were trained to be the same. It’s wonderful that we now have more options available to us, but that means parents aren’t quite sure what they’re raising their kids to be. Success often gets defined in terms of sports, academics, or extracurricular involvement, but that doesn’t always translate into the real world, especially when kids are over-scheduled and helicopter-parented. I think trying to teach kids to think critically about the big picture of one day being able to contribute to society, support a family, or plan for your own future is so important. But we are just at the beginning of all this!

    • It a new challenge Kalie, one our parents really didn’t face.I’m sure most of us are up for it, but think change within our school systems will lag behind. That why it’s so important for us parents to be on the top of our parenting game.

  7. I need to be more strategic about my career as well. I’ve had good progression in my career, income, and responsibility over the years, but most of it wasn’t intentional. I kind of just did something, then did something different – changed projects and took on more responsibility – but didn’t take the time to map anything out. Now I’m at a level where I can’t really just wing it anymore, so I’ve been much more intentional about the projects I take and the discussions with my management team. Great reminder!

  8. I have been strategic about my career, and was already working in still in college by taking on extra roles and internships that fitted the road I wanted to follow.

    What helped for me is try out much and often at an early age, follow up on what gives you energy and find out what you have to do to get there.

    I’ve been thinking about this lately, but more the other way around. My focus has always been on building up a successful career. I’m still under 30, but I don’t have that same drive anymore. Rather I focus on doing what I like, working on what I am good at and develop my skills along the way. And the career will follow automatically.

    • Good for you for having such a great head start. Often when you follow what makes you the happiest or most passionate about good things follow. Continued success!

  9. Great reflection Brian! The value of critical thinking really is irreplaceable. Your point about being envious of homeschoolers is an interesting one – I definitely see how that could breed a little more independence of thought than passively learning a rote curriculum in a classroom!

    • Thanks, Jay. School systems are just so slow to react to the changing world we live in. Homeschoolers have such an advantage to be more agile.

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