8 Tips for Making Big Career Decisions

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At the time I’m writing this, I am currently about to make a big career decision 😂 Perhaps by the time you’re reading this, those decisions will have been made, but remember that this is past-Aidan writing and he doesn’t know what’s ahead yet. I am right here with you.

Nonetheless, I think it’s a common thing that we all find ourselves at forks in the road regarding our careers and futures every once in a while. For some people (and at certain stages of life), these events might happen more frequently. Other people, like my father in law, only had a few in his early years before (happily) settling into a 30+ year tenure at an accounting firm.

I don’t believe “finding happiness” should be the sole, nor even primary, factor to consider when making any decision in life. Happiness is fleeting; it ebbs and flows like the tide. But joy is long lasting, and it will suit you far better to find joy before you work on happiness, which is high maintenance and finicky at best.

Wheresoever you should find yourself right now, I hope these handful of tips and things to remember will help you as you make big career decisions.

1. Your dependents come first

Christian worldview incoming, so if that offends you… well, I’m not really going to apologize. Skip to the next one if you must.

If you have kids or a spouse, I believe you are obligated to provide for them.

Don’t care if you and your spouse are DINKs (double-income-no-kids) and very well off: you are compelled, due to the marital covenant you made, to consider how your career impacts your spouse and marriage as a whole.

As a man of Christ, as a husband, and as a father, I firmly believe it is my duty to provide for my family. Full stop. I’m happy to report though that it is not just my duty, it is my joy! Nothing comes anywhere close to fulfilling me as deeply as knowing I am able to provide a happy, loving, supportive environment for my wife + kids to grow, flourish, and become more of who they were created to be.

It’s my belief that, especially as men in similar situations, as the leaders of our families, we have this obligation to our dependents.

Now, I fully recognize two important things:

  • Accomplishing this can look wildly different from one family to another, and

  • This has less to do with money (although it does to some extent) and more to do with stability.

I’m not at all saying that there can’t be stay-at-home dads, or living situations where the wife provides the majority of the income. Not at all. But what I am saying is this:

Every decision in my life first needs to answer, “How does this impact my family?”

If the answer is positively, then we can continue the conversation. If it’s negative for any reason, we must proceed with the utmost of precautions.

I am ashamed to say that there have been a handful of times in my life where my family has been put though stressful situations because of my laziness and indecision in what I want to do with my career. I allowed my job to dictate my happiness (and joy) and that is so, so wrong. I am deeply grateful to have learned from those mistakes, and to have had a wife who has forgiven me and empowered me to be better than I was yesterday.

If you want to ignore just about everything in this entire portion, at least consider this: your decisions likely impact more thanjust your life alone. And when you had those kids, when you took on that partner (heck, even if you’re just dating), you gave up certain autonomies and independencies. Step up to the plate, and follow through on previous decisions you’ve made. It is wrong for your family to suffer due to your lack of responsibility.

2. Consider every option

At least for me, it’s easy to fall into the trap of thinking that the momentum of my career is the direction I must go. This is false. I am not a river. I am a car on a road. I can veer any which direction I want at any point. In fact, I make the road.

Don’t get pulled into the thought that there’s anything you must do.

Even for the options that seem less likely, I firmly believe we are capable of far more than we think. I have seen more people succeed at chasing their dreams than I have seen fail. And as a result of that, I wish we (as a people) were more brave about running after the thing we really want.

It’s also ok if your dreams change. Oftentimes you’ll find that getting what you want didn’t satisfy you quite the way you thought it might. At that point, it’s okay to move on, or to backtrack, and change what it is you have your eyes fixed upon.

3. Seek trusted counsel

Ideally this is someone like a spouse, a childhood best friend, or in some cases it can be a really exceptional coworker who knows you outside of work + would care for you outside of it.

Talk things out with this person. Ask them: Do you see this future for me? Do you see anything I haven’t considered?

We are often too much in our own head to be able to see things clearly or objectively. Having someone who we consider wise, and who knows us deeply, can be a huge asset when trying to decipher the path we ought to take.

4. Pros + Cons list, baby

Seems basic, but it’s a staple for a reason. I frequently find myself jumping back and forth between trains of thought in such a way that I get exhausted of thinking the same thoughts.

Writing things down allows you to see it in black and white. Don’t repeat yourself on paper. You might be surprised how much more obvious the answers become when you can see them—visually—right in front of you.

5. Consider the long term

Picture yourself in 20 years (can you?). Does choosing one path over the other right now bring you closer to that goal than the other? I’m not talking immediate satisfaction or gratification: we’re really looking at the bigger picture here. Sometimes that might mean 2-8 years of schooling before you get a job somewhere and climb the ranks in your dream job.

Short term suffering is worthwhile to long term gain.

It is way too easy—and I’ve seen it happen just one too many times—to keep your head down on what’s immediately in front of you and forget to plan for where you actually want to go. Like I said in #2, the momentum of your current career or life doesn’t have to dictate where you end up.

6. Think beyond money

Maybe it’s just me, but I think there might be a shift in society where we’re really recognizing all the money in the world doesn’t mean anything if you can’t enjoy it. While financials play a huge role in choosing any one job prospect, there are points of diminishing return on money equating happiness.

Look at the way each career path comes with its own lifestyle.

Shift work? On call? Choose your own schedule? Location specific? Work remotely? Vacation weeks? Overtime?

There’s so much more to consider than just the cash that’ll end up in your bank account. In fact, check out this list of 15 metrics that are good ways to consider your entire life.

7. Actually follow through on something

Dear lord, I think one of the greatest weaknesses I’ve seen in some people is their “one foot on the dock, one foot in the boat” approach to life decisions. These people often stagnate for years at a time, and end up sort of falling into a decision by way of circumstance.

I’m not saying you can’t be indecisive, or have a period of being uncertain about something. Take the time to contemplate what’s ahead of you! I think you should do that all the time.

But for all that is good, please just make a decision and go after it.

I believe you are going to succeed more often than you might fail. And it is so, so easy to have one foot on the dock, one in the boat, and fall into the water, having squandered both opportunities.

8. Change your mind if you’ve gone the wrong way

Last thing I’ll preach about today:

I think it’s one of life’s greatest skills to be able to say “I was wrong.”

I’ve seen waaaaaayyyyy too many relationships fall apart because someone was too proud, or too oblivious to their own self, to admit they made a mistake. Learn how to admit you messed up. Learn how to say sorry. Learn how to ask for forgiveness.

I think if you can do those 3 things, there aren’t many major life decisions you can screw up without recovery.

Of course, every decision has consequences. You might not be able to claim that job offer in 6 months when you realized you should have!

You can almost always turn back around.

Not even tattoos are permanent anymore.

If you’ve found yourself having made a grave mistake, please, please admit it and make it right. You might feel some temporary shame, but in hindsight, it will have been better to have spent a little bit of time going the wrong way than to spend the rest of your life digging your grave because you were too proud to admit your faults.

In conclusion:

Career decisions are tricky!! It is hard to know what path to choose sometimes. But not every door is going to be closed off to you before you have to walk through one. That’s ok. Don’t live your life at such a slow pace.

The world is your oyster, my friends. I think if you want most things in life bad enough, you will find a way. The question really isn’t, “Can I do this?”, it’s “How badly do I want it?”.

Aidan Hennebry

Hey 😀🤚🏻 I’m Aidan, and regularly share a variety of content on my two blogs: Hennebry.ca is full of articles on marketing, managing, and shaping your career to suit your life; ManNotBrand.com is my personal blog on my various passions, interests, and philosophies on life.

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