5 Career Moves That Look Risky But Aren't (And the 1 That Is)
What working at Amazon, Microsoft, and Starbucks taught me about calculated risk vs. reckless gambling
I’ve made some career moves that made people (even close family and friends) think I was crazy.
Going back to school as a married adult with two kids.
Joining a renewable energy startup after years at Microsoft and Amazon.
Moving my family across the country for a role that didn’t fully exist yet.
Each time, someone pulled me aside and said: “That seems risky.”
And each time, they were wrong.
Here’s what I’ve learned after 15 years climbing from factory floors to Fortune 500 operations:
Most “risky” career moves aren’t actually risky. They just feel risky because they’re unfamiliar.
The truly risky move? Staying where you are because it feels safe.
5 “Risky” Moves That Actually Aren’t
1. Leaving a “Good” Job for a Better Opportunity
The fear:
“What if the new company isn’t what I think it is?”
“I’m giving up stability for uncertainty.”
“My current job is fine. Why rock the boat?”
I hear this constantly from people I mentor. They’re in a job that’s... fine. Not great, not terrible. Just fine. And they’ve been offered something better (more money, better title, exciting project) but they’re paralyzed by the fear of leaving what they know.
The reality:
If your current job is just “fine,” you’re already at risk. You’re at risk of stagnation, of becoming comfortable, of waking up five years from now and realizing you haven’t grown.
Here’s what most people miss: You’re more marketable while employed. You have leverage. You can negotiate. You can be selective. The moment you’re desperate and unemployed? That leverage evaporates.
Good opportunities compound. Each better role opens doors to even better roles. Each new challenge makes you more capable. Each expanded network makes you more connected.
And the worst case? It doesn’t work out and you find another “fine” job in six months. You know how I know? Because you just left a fine job. You can find another one.
When I left Amazon, people asked: “Why would you leave? It’s stable, you know the team, you’re doing well.”
Because “doing well” in a comfortable role is different than being challenged in a stretch role. Within two years in a fast-paced startup environment, I’d grown more than I would have in five years of “doing well” at my previous company.
The calculation:
Upside: Career acceleration, higher compensation, expanded network, new skills
Downside: Might need to job search again in 12-18 months (which you’re capable of doing)
Risk level: 2/10
When it IS risky:
Joining a company that’s clearly failing (declining revenue, mass layoffs, leadership exodus)
Taking a role where none of your skills transfer (accountant → professional athlete)
Burning bridges on the way out (never do this)
The key question:
“If this doesn’t work out, can I find another job at this level within six months?”
If the answer is yes, it’s not risky. It’s just uncomfortable.
2. Taking a Role You’re “Not Ready For”
The fear:
“I don’t have all the qualifications they’re asking for.”
“What if I fail publicly and everyone sees?”
“The imposter syndrome will eat me alive.”
I’ve watched talented people turn down promotions because they “weren’t ready yet.” They wanted to be 100% qualified before they said yes. So they stayed in their comfortable role, got 100% qualified, and then... the opportunity had moved on to someone who was only 70% qualified but said yes anyway.
The Reality:
Companies don’t hire for perfection. They hire for potential.
If you have 60-70% of what the role needs, you can learn the rest. And here’s the secret: everyone is figuring it out as they go. The difference between the people who get promoted and the people who don’t isn’t competence, it’s confidence to say “I’ll figure it out.”
You’ll never feel ready. Readiness is a myth. I’ve never taken a promotion where I felt fully prepared. Every time, I was maybe 70% qualified. The other 30%? I learned it in the first 90 days.
And failing in a stretch role teaches you more than succeeding in a comfortable one. I’ve learned more from the projects that went sideways than from the ones that went smoothly.
Every promotion I’ve received, I wasn’t “ready.”
When I was promoted to lead my first team at Starbucks, I’d never managed people before. When I joined Amazon to lead multi-million dollar operations, I’d never worked in e-commerce. When I was asked to build supply chain operations for a renewable energy company, I’d never worked in clean energy.
Each time, I was 60-70% qualified. Each time, I figured out the other 30%. That’s the job.
The calculation:
Upside: Accelerated growth, higher compensation, expanded responsibilities, bigger network
Downside: Steep learning curve, temporary discomfort, possible failure (which you can recover from)
Risk level: 3/10
When it IS risky:
The role requires deep technical expertise you truly don’t have (you can’t “figure out” how to be a surgeon)
The company has unrealistic expectations (turn around a failing division in 30 days)
There’s zero support, mentorship, or training available
The key question:
“Do I have 60-70% of what this role needs?”
If yes, take it. Learn the rest. You’ll be fine.
3. Going to a Smaller Company After Big Tech
The fear:
“I’m leaving [*insert Fortune 500*]’s brand name on my resume.”
“Startups fail all the time. Big companies don’t.”
“I’ll lose my compensation, benefits, and prestige.”
I’ve had this conversation dozens of times with people who’ve spent years at big tech companies. They’re offered an exciting role at a smaller company (maybe 50 people, maybe 500) but they’re terrified of leaving the brand name behind.
The reality:
Big company experience doesn’t disappear when you leave. It stays on your resume forever. “Former Amazon” or “Former Microsoft” is a permanent credential that opens doors.
But here’s what people miss: At a smaller company, you learn faster because you wear more hats. At Microsoft, I was responsible for one slice of supply chain. At a 200-person renewable energy company, I built supply chain from scratch. I touched everything—strategy, systems, private equity financing, digital transformation, vendor negotiations, board presentations.
Which experience made me more valuable? The one where I did ten jobs, not one.
And here’s the other secret: You can always go back to big tech. They love boomerang employees. People who left, learned at startups, and came back with broader skills? They’re more valuable, not less.
After Microsoft and Amazon, I joined smaller companies in renewable energy.
Did I miss the free food and the big budgets? Sure. But I learned five times faster because I had to solve problems without an army of specialists. When I wanted to talk to Fortune 500 companies again, I could—with better, broader skills.
The calculation:
Upside: Faster learning, broader skills, more impact, potential equity upside, you matter more
Downside: Less structure, possibly lower short-term comp, you might have to solve problems yourself
Risk level: 4/10
When it IS risky:
The company is clearly failing (no revenue, no product-market fit, everyone’s jumping ship)
You’d be employee #3 with no customers (very different from employee #50)
The compensation cut is unsustainable (you can’t pay your bills)
The key question:
“Will this experience make me more valuable in 2-3 years?”
If yes, the brand name on your resume today doesn’t matter as much as you think.
4. Asking for a Significant Promotion or Raise
The fear:
“They’ll think I’m entitled or ungrateful.”
“What if they say no? I’ll have damaged the relationship.”
“I’ll look greedy or out of touch.”
This is the “risk” that costs people the most money over their careers. They’re underpaid, they know it, and they’re too scared to ask. So they wait for their manager to notice. And wait. And wait.
Meanwhile, their colleague who’s 10% less qualified but 100% more willing to advocate for themselves asks and gets a 20% raise.
The reality:
Not asking is a guaranteed zero. Asking has upside.
Good managers respect self-advocacy. They want you to stay. If you’re underpaid and unhappy, they’d rather give you a raise than replace you. Replacing you costs more (recruiting, onboarding, ramp time) than paying you fairly.
The worst realistic outcome of asking? They say “not yet” and you get a timeline. “Let’s revisit this in six months after you complete [specific milestone].” Now you have a roadmap instead of uncertainty.
And if they’re offended that you asked? You’re at the wrong company.
Early in my career, I was terrified to ask for a raise.
I was at a company for two years, performing well, but I hadn’t seen a significant increase in compensation. I watched a colleague (who was good, but not better than me) ask for a 20% raise. And get it.
I asked the next week. Got 15%.
The only risk was the two minutes of discomfort in the conversation. The upside was thousands of dollars a year for the rest of my time there, compounded across my entire career.
The calculation:
Upside: More money, better title, expanded responsibilities, respect for advocating for yourself
Downside: A temporarily awkward conversation
Risk level: 1/10
When it IS risky:
You’re about to be fired and don’t realize it (read the room)
You just got promoted three months ago (timing matters)
You’re asking for something wildly outside market norms (VP title with two years of experience)
The key question:
“What’s the worst realistic outcome if they say no?”
Usually, it’s: Nothing happens. You try again in six months. That’s it.
5. Changing Industries After Years of Specialization
The fear:
“I’m starting over from scratch.”
“My years of experience won’t transfer.”
“I’ll take a massive pay cut and lose all my credibility.”
“I’ll be behind people who’ve been in this industry their whole careers.”
Of all the “risky” moves on this list, this one feels the scariest. You’ve spent a decade building expertise in retail, or logistics, or tech and now you’re thinking about jumping to a completely different industry. It feels like throwing away everything you’ve built.
The reality:
Transferable skills are more valuable than industry knowledge.
Leadership is leadership. Operations is operations. Problem-solving is problem-solving. These skills work everywhere. What changes is the context, and context can be learned.
Industry insiders have depth but often lack perspective. They’ve done things the same way for so long, they can’t see what’s broken. You, coming from outside? You see everything they’ve become blind to and that fresh perspective is valuable.
And industries are converging anyway. Supply chain used to be separate from technology, now it’s the same thing. Sustainability used to be separate from operations, now it’s integrated. The walls between industries are dissolving.
You’re not starting over. You’re adding dimensions. Your previous experience doesn’t disappear, it compounds with your new experience to create a unique combination.
I’ve worked in cloud, retail, satellite broadband technology, and renewable energy.
Each time I switched, someone said: “But you don’t know [this industry].” True. But I knew how to optimize operations, build teams, manage vendors, and solve complex problems. Those skills are universal.
And every time I switched industries, I saw opportunities that insiders missed. At the renewable energy company, I applied supply chain practices from Amazon that the clean energy industry hadn’t adopted yet. That combination—tech company rigor plus renewable energy mission—made me more valuable, not less.
The calculation:
Upside: Renewed energy, expanded network, fresh perspective, new opportunities, intellectual stimulation
Downside: Learning curve, possibly lower initial compensation, you’ll need to prove yourself again
Risk level: 5/10 (the highest on this list, but still manageable)
When it IS risky:
The new industry requires credentials or licenses you don’t have (medicine, law, engineering)
The pay cut is more than 40% (very hard to recover from financially)
The new industry is clearly declining (newspapers, coal mining, etc.)
The key question:
“Are my core skills—leadership, operations, strategy, problem-solving—valuable in this new industry?”
If yes, the industry-specific knowledge can be learned. Skills transfer. Context doesn’t.
The 1 Career Move That IS Actually Risky
Staying Put Because It Feels Safe
Let me tell you about the riskiest career move I see people make:
Staying in a job that’s “good enough” because leaving feels too uncertain.
Here’s why this is the most dangerous move you can make:
1. Stagnation compounds negatively
Skills become outdated. Your network stops growing because you’re talking to the same people every day. The market moves forward while you stand still.
What felt like a good role in 2020 might be obsolete by 2025. AI is reshaping supply chain. Automation is eliminating middle management. Remote work is globalizing competition for your job.
If you’re not growing, you’re falling behind. And you won’t notice until it’s too late.
2. The market moves without you
Your “safe” job might not exist in five years.
I’ve watched this happen. People who stayed at companies that seemed stable—retail giants, logistics leaders, traditional manufacturers—because they were “too risk-averse” to leave. Then the industry shifted. E-commerce killed retail. Technology disrupted logistics. Suddenly their “safe” job disappeared and they hadn’t built skills that transferred. They weren’t laid off because they were bad at their jobs. They were laid off because their jobs stopped existing.
3. Regret is expensive
I mentor professionals in their 40s and 50s who are talented, capable, and deeply unhappy. When I ask what happened, the answer is almost always the same:
“I had opportunities in my 30s. I didn’t take them because they seemed risky. Now I’m stuck.”
Financial cost: They stayed in underpaying roles for 10-15 years. That’s hundreds of thousands of dollars in lost lifetime earnings.
Emotional cost: They look back and say “I should have...” That regret weighs on you.
Opportunity cost: All the doors that never opened because they didn’t walk through the first one.
4. You’re modeling the wrong lesson
If you have kids, they’re watching how you handle your career.
When you choose comfort over growth, you’re teaching them to do the same. When you talk about the opportunity you’re too scared to take, they learn that fear should stop them.
I want my sons to see me take calculated risks. To watch me leave “good enough” jobs for better opportunities. To know that staying comfortable is more dangerous than being uncomfortable.
The proof:
The unhappiest people I know aren’t the ones who took risks and failed. Those people learned, recovered, and are now doing something they love.
The unhappiest people are the ones who never took the risk. Who stayed in the safe job for 20 years and woke up one day realizing they’d built a career they didn’t want.
The calculation:
Upside of staying: Comfort (temporary), familiarity, no immediate stress
Downside of staying: Stagnation, regret, shrinking opportunities, obsolete skills, wasted potential
Risk level: 9/10
This is the career move that actually ruins careers. Not the risky opportunities you take. The safe opportunities you don’t.
The Framework: How to Know If a Risk Is Worth Taking
Okay, so if most “risky” moves aren’t actually risky, and staying put is the real danger, how do you know when to take a leap?
Here’s the framework I use:
Question 1: Can I recover if this fails?
Ask yourself:
Do I have 6-12 months of savings?
Are my skills transferable? (Can I get another job if this doesn’t work?)
Do I have a safety net? (Family support, network, geographic flexibility?)
If yes to at least two of these, you can recover.
Most career “failures” aren’t actually catastrophic. They’re:
“I’ll need to find another job” (you can do this)
“I’ll look foolish for a few months” (you’ll get over it)
“I’ll make less money temporarily” (emphasis on temporarily)
Question 2: Will I regret NOT taking this risk in 10 years?
This is the regret-minimization framework, and it’s the most powerful question you can ask.
Imagine yourself at 50 or 60. You’re looking back at your career. You think about this opportunity you had—the one you’re scared of right now.
What does that older version of you think about your decision?
If they’re grateful you stayed safe → don’t take the risk
If they’re indifferent → it’s not that important
If they’re disappointed you didn’t try → take the risk
I’ve made this mistake. There are opportunities I turned down in my 20s because they “seemed risky.” Now, in my mid-30s, I look back and think: “That wasn’t risky. That was just uncomfortable. I should have done it.”
I’m not making that mistake again.
Question 3: What’s the actual worst-case scenario?
Not the catastrophic fantasy your brain creates at 2am.
Not “I’ll be homeless and my family will disown me and I’ll never work again.”
The realistic worst case.
For most career moves, the realistic worst case is:
“I’ll be back in the job market in 12 months”
“I’ll have learned something valuable”
“I’ll have tried, so I won’t wonder ‘what if’”
That’s it. That’s the downside.
And here’s what people miss: Even in the “worst case,” you’re not worse off than you are now. You’re just back where you started, with more knowledge.
Putting It All Together
So here’s what I want you to take from this:
The career moves that feel risky (leaving a good job, taking a stretch role, switching industries) usually aren’t risky at all. They’re just unfamiliar.
The career move that feels safe (staying where you are because it’s comfortable) is the riskiest move you can make.
Before you turn down an opportunity because it “seems risky,” ask yourself:
Can I recover if this fails?
Will I regret not trying this in 10 years?
What’s the realistic worst case?
If you can recover, you’ll regret not trying, and the worst case is temporary discomfort?
That’s not risky. That’s called growth.
Take the scary opportunity.
You’ll figure it out. You always do.
And if it doesn’t work out? You’ll have learned something. Which makes the next scary opportunity a little less scary.
The only career move you’ll definitely regret is the one you were too afraid to try.
Rooting for you,
Justin
P.S. If you found this helpful, share it with someone who’s deciding whether to take a leap. Sometimes we all need permission to be uncomfortable.
And if you want weekly career insights like this—lessons from factory floors to Fortune 500 boardrooms—subscribe to Career Field Guide. It’s free, and I promise not to waste your time.
Hey, great read as alwas. Totally agree stasis is the real risk. For us devs, it's often just finding the next interesting bug, no?