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Don’t Make A Big Career Move Without Checking These 3 Boxes First

Worried it’s too risky right now? This checklist can help you decide whether to bide more time or take the leap. (P.S. It shouldn’t be a “leap.”)

Don’t Make A Big Career Move Without Checking These 3 Boxes First
[Photo: Glenn Carstens-Peters/Unsplash]

Timing isn’t everything when it comes to risky career moves, but it’s no minor consideration, either. Sure, you first need to find your unique purpose, especially if you’re feeling burned out by a meaningless job. And then you need to figure out how to make a living off that passion. Those are challenging steps all on their own. Once you’ve laid that foundation, though, the “when” becomes your biggest concern, and knowing exactly how to time your switch isn’t always easy.

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But no matter what type of career move you’re contemplating–whether it’s switching employers or industries, or even jumping into self-employment for the first time–there are three key criteria that you absolutely need to nail down first. If you can’t, you should probably wait a little longer to take the leap.

1. “I’ve Been Practicing This Work Daily For The Past Two Years”

Does that sound like a tall order? It should.

It’s one thing to spend a lot of time talking or thinking about your dream job, and it’s another to spend a lot of time actually doing it in regular, incremental ways. Having a passion that you’re striving toward is important, and for a time, it’s fine for that to remain some far-off, distant concept. Ultimately, though, you’ll need to start taking real, concrete steps toward it–otherwise you’re just stalling. Many of us keep on talking about our dreams in the future tense because it’s easier than doing the daily work to make them a reality.

Those who go on to accomplish their dreams do something different. They take whatever time they have–usually an hour or two–and dedicate it to that activity. They don’t just talk about it. They do it. I call this the “baby-step strategy,” and it’s crucial to the success of any artist, author, entrepreneur, or would-be career changer. If you want to do something you love for at least eight hours a day every single day, you need to start by doing it just a little bit every single day.


Related: Your 5-Week Plan To Starting A Side Hustle Over Your Lunch Break


The good news is that you can start small and work on it over a long timeline. Two years isn’t a hard-and-fast rule, but it’s a long enough timeline to give you ample practice without carving out tons of time (which you probably don’t have anyway) in an ordinary workweek. The point is to take the time to find out how much you really enjoy this work–not just as a side gig but on a regular basis–and whether you’re cut out to do it full-time.

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If you can’t maintain a daily discipline of an hour or so working on the side, then you have no business quitting your job to do it full-time.

2. “I’ve Replaced Half My Monthly Income For The Past 90 Days”

In his excellent 2011 book, EntreLeadership, author and radio host Dave Ramsey suggests that the work you’re doing on the side should be pulling in at least half your salary when you’re devoting fewer than 20 hours a week to it. In other words, your time-to-money ratio needs to be on par with your day job before you quit your day job.

If you can get your side hustle to consistently generate that much value for at least three months in a row, then it stands to reason that if you increase the time you’re spending on that activity, you’ll increase your income, too. Put simply: If you aren’t yet making enough money off the line of work you’re hoping to switch into, then you need to keep working on it until you are.

3. “I’ve Won The Support Of My Family, Friends, And Coworkers”

It’s common to dismiss the criticism of those who love us as “jealousy” or the detractions of “haters”–and sometimes that’s exactly the case. But if you can’t repeatedly find people close to you who agree that this is the right move at the right time, then there’s a good chance you’re the one who’s off-base.

Personally, I knew it was time to quit my job working as a marketing director at a nonprofit when multiple people–from my wife to my friends to my mentor–all told me, “Jeff, it’s time.” In fact, when I gave my notice, even my boss said to me, “I’ve been waiting for this. I knew it was time for you to move on. You’ve outgrown us.”

Can you find at least one person in each of those categories–friend, coworker, family member–to affirm this dream? Do you they see your vision as clearly as you do? Do they “get it”? It doesn’t have to be everyone. But someone should be firmly on your side in every major sphere of your life. Someone should see what you see and be cheering for you.

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I’ve written before that every story of success is a story of community, and this is more true than ever when it comes to making major career moves. You won’t make it just on your own, so you’ll need the help of others who believe in you. And if nobody does, that should give you pause. Maybe the idea isn’t strong enough yet, or maybe you just haven’t communicated it well enough. Regardless, that’s a sign you need to wait a little longer and work a little harder before taking the leap.

Indeed, “leaping” is probably the wrong way to think about it. You can’t just jump and hope the net will appear beneath you. You need to stitch the net first–patiently, deliberately, and sometimes painstakingly–but not necessarily all on your own. Like most things, great careers are built gradually and intentionally, and by many hands. When you’re ready to confidently check each of these three boxes, you’ll know it–and others will, too.

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