How to Make a Career Change: 3 Insider Secrets For Success

How do you know when to make a career change?

Sometimes, the right path isn’t clear.

Senior year of college, I had a great job offer. It would have impressed my friends and parents, I would have made a lot of money — but there was something in the back of my head saying no.

My other option was to stay in school for a fifth year, get a graduate degree, and soak up what college still had to offer me.

To decide, I tried all the things you would think of, like writing down a list of Pros and Cons, and sketching out a “5-year plan” (ugh, who the hell knows where they’ll be in 5 years?).

But I kept coming back to this idea that I “should” take this job because it was the right thing to do. And just as I went to call and accept the job offer, I stopped short. I couldn’t shake the nagging feeling, so I sent an email to one of my mentors.

“I have no idea what to do,” I wrote. “How would you think about this?”

We met for coffee and I spilled the beans. Like a great coach, he didn’t tell me the answer. He showed me a new framework, a way to think about how to make a career change. After I talked it through out loud, I actually made my decision on the spot: I’d stay in school and enjoy my last year.

Smiling, he finally revealed what he’d thought: “You were going to leave Stanford so…what? You could get a one-year head start on being an employee…which you’ll be for the rest of your life?”

More than 10 years later, I still remember that one sentence. But even more, I still remember the framework he taught me for making a wise decision…one that, in the end, turned out to be the 100% correct one.

Remember the final scene in Indiana Jones and the Last Crusade, where Indy has to choose the Holy Grail? He could choose the shiniest cup, but (spoiler alert) because he has an intellectual framework, a “map,” of what the Holy Grail looks like…he chooses correctly: the old cup that would have probably been owned by a carpenter. That single decision saves the life of his father.

What would you give to have someone share these frameworks with you? For someone to help give you clarity over the big decisions? The ones where, if you make the wrong decision, you can get stuck in a decade-long rut that becomes increasingly hard to climb out of…or if you make the right one, your career can soar and leapfrog others who didn’t have the prescience to choose correctly?

Let me share 3 of these frameworks with you today:

  1. Reverse Engineering
  2. Yes and Yes
  3. Regret Minimization

Career Change Framework #1: Reverse Engineering

One technique you can use to make a career change is to “reverse-engineer” the careers of people you admire. You can do 50% of this online, simply by studying their career history (use LinkedIn) and analyze how they ended up where they did.

What was their first job out of college? How did they switch industries? Oh, they got laid off when their third employer shut down? How did they transition then?

But there’s a twist.

Most people take that knowledge and stop. Then they copy the exact same career moves. I call this Moronic Modeling. “Ah, got it! So I should start working at a magazine…then switch to TV…then finally write a book and become famous!” No, dumbass, you’re copying the tactics without understanding why it worked.

It’s like an aspiring chef going to a restaurant, eating the food, then thinking that knowing the ingredients alone will let them make the exact same dish. Wrong!

There’s another part: Understanding the context. This means understanding WHY the person made those decisions, not just WHAT those decisions were.

For example:

  • When should you take a job with a 40% pay cut?
  • Under what circumstances should you move to a small city vs. a big one?
  • How do you know when to leave your company?
  • Should you aim for more money or work/life balance?
  • What do you do if you hate your boss?

If you understand the WHY — the frameworks to make the right decisions for you — you can adapt them to almost every possible situation you’ll encounter.

Instead, most of us get so stressed about these choices that we procrastinate and do nothing.

We let other people make the decision for us. We spend our time wondering “what if…?” What if I did things differently?

People spend their ENTIRE LIVES stuck in this cycle (mostly starting around 30)…wondering why our careers aren’t going the direction or at the velocity we want them to.

And when we do come across an opportunity, we freeze, uncertain how to proceed, terrified of making the wrong mistake.

Or we sit at our desk in a job we never should have taken, wondering where we went wrong and if it’s too late to change? Or if we’ll know how to make the right decision the next time we get our shot?

Career Change Framework #2: Yes and Yes

It’s interesting when people let their barriers slip out in their actual language. Usually, they don’t even realize they’re doing it.

Guy 1: “So you started going to the gym?”
Guy 2: “Yeah, I actually kinda like it now. You should come.”
Guy 1: “I don’t want to go to the gym every day for the rest of my life to lose weight. I could never do that!”

Guy 1 is demonstrating an example of an “extreme-reach barrier” — the assumption that if you want to do something, you have to go to the COMPLETE EXTREME to do it at all.

This allows him to rationalize the fact that he doesn’t go, even though he could get benefits from going 2-3 times per week. I hate him.

Another way we do this is by creating false dichotomies. “Ramit, should I do X or Y?”

My answer is usually “Yes and yes.” This is the idea that top performers don’t do X or Y — they do both, and they’re better at it than everyone else.

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Career Change Framework #3: Regret Minimization

Not ONE of us ever graduated from college saying, “Yes! I want to be a replaceable cog in the machine! I want to spend all day doing Excel and listen to my boss tell me how I ‘should be lucky to have this job’ and how ‘the economy just won’t let me give you a raise this year.’”

So how do top performers seize impressive, rewarding, lucrative careers…while average performers wind up as cogs in the machine, waiting for someone to recognize their hard work and finally reward them? (A reward which almost never comes.)

It’s not an accident.

Top performers DO have strategies and tactics they use, which average performers don’t.

One of the people who’s taught me the most about these strategies is Ben Casnocha. Ben is one of the most sophisticated thinkers on careers today — he’s been an entrepreneur, author, and right-hand man to one of Silicon Valley’s godfathers, Reid Hoffman.

How does someone so young make these career moves?

I wanted to know — and I wanted to reveal these frameworks for you. That’s why I invited Ben into my studio to pick his brain about how to make a career change, and how anyone can make the most of these defining career opportunities.


How to write a resume for a career change

No matter what job you’re applying for, your resume should not be a list of facts.

This is especially true if you are making a career change. Your resume should craft a narrative. How will your experience up to this point help you in your new career?

Ask yourself, “After someone reads my resume for 10 seconds, what is the one thing they should remember about me?”

If you just list your education and job history, what will they remember? But if you call out key courses you studied or professional accomplishments, you’re getting closer to being memorable.

“Oh, that’s the candidate who started that e-commerce website for tweens.”

I spent over 100 man-hours crafting the perfect resume. That’s not an exaggeration. Every word was carefully considered. Each line added a powerful piece to the narrative. When I was done, I tested it and it worked. The resume got me jobs at top companies like Google, Intuit, and a hedge fund.

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Written by

Host of Netflix's "How to Get Rich", NYT Bestselling Author & host of the hit I Will Teach You To Be Rich Podcast. For over 20 years, Ramit has been sharing proven strategies to help people like you take control of their money and live a Rich Life.