The key to making a successful career change is to clarify what you actually want, use stepping stone roles to reduce risk, build experience before you quit, grow your network through real conversations, and reshape your resume to tell a compelling story.
Step 1: Be Clear on What You Actually Want
Before quitting your current job, look inward and reflect on what you truly want out of your career.
Figure out what’s not working in your current role
To assess this rationally, without making emotionally-charged decisions, make a simple list of what’s been draining you at work. Maybe it’s unnecessary meetings, a lack of creative freedom, or the sense that the work you do doesn’t matter. These pain points can help you clarify what you want to avoid in your next role and find what aligns best with you.
By pinpointing what you want and why your current role no longer aligns with the career path you’re building, you’ll also be able to leave your job without burning bridges.
Identify what energizes you (not just what sounds impressive)
To figure out what energizes you, pay attention to the tasks that make you lose track of time. If you can stay focused and engaged without feeling distracted or mentally drained, you’re likely doing something you genuinely enjoy.
Aside from that, observe what you read about in your free time or the activities that make you forget to check your phone. These natural tendencies can reveal your true interests and passions without being shaped by external expectations or how impressive something might seem to others.
If you’re wondering how to turn those passions into a career that pays, check out these guides:
Don’t expect a “perfect fit” (look for alignment, not perfection)
No job or career offers 100% enjoyment, fulfillment, and high pay all at once. That ideal doesn’t exist.
Even dream jobs come with boring tasks and frustrating days. Instead of chasing the “perfect job,” aim for a 70 to 80 percent alignment with your interests, values, and strengths.
Once you’re in the role, you’ll often have the chance to shape it accordingly. That’s why it’s more important to focus on the core elements that matter most to you.
Step 2: Use Stepping Stone Moves to Your Advantage
A complete 180-degree career change might sound thrilling, but it can also be risky, as a much steeper learning curve is to be expected.
Instead of diving in headfirst, consider using stepping stone moves to gradually transition into your ideal career.
Change industry or role (but not both at once)
Trying to switch what you do and where you do it at the same time makes the transition much harder than it needs to be.
For example, if you’re a marketing manager in healthcare and want to become a software developer in tech, consider starting by moving into tech as a marketing manager. Shifting one variable at a time, whether it’s the industry or the role, makes the change more manageable and provides a solid foundation to build from.
Look for internal transfers before external jumps
If you’re looking to change your role, start by exploring opportunities within your current company before you search elsewhere.
Your current company already knows your value and work ethic, which makes internal moves much easier than convincing a new organization to take a chance on you, especially if you don’t have much experience in the new role you’re aiming for.
Even if a full transition isn’t possible right away, volunteer for projects in your target department. This helps you build relationships with people doing the work you’re interested in. Once you’ve established a strong reputation, you’ll have advocates who can vouch for your potential when positions open up.
Ask to shadow someone, volunteer, or get a mentor’s help
Not sure if your target career is the right fit? What we imagine a role to be can turn out to be completely different in reality.
To test the waters, ask if you can shadow someone in that role for a day. You can also volunteer for projects that expose you to new areas of the business you’re interested in.
It’s also worth finding a mentor who can help guide you through the transition. A good mentor can offer perspective, feedback, and clarity on your next steps. Here’s a list of questions to ask a mentor to help you get the most out of that relationship.
These low-risk experiences give you real insight into the role you’re interested in, while also showing your initiative towards upskilling and adding value to the company.
Step 3: Build Experience Before You Decide to Quit
It’s not easy to jump into a different career with no prior experience. Use this transition period to start building the skills and experience that will move you closer to your next role.
Use freelance, volunteer, or side projects to gain skills
You can develop relevant skills and experience while keeping your day job by taking on small-scale freelance gigs, evening volunteer work, or weekend projects.
These are great opportunities to create tangible proof of your skills and show future employers what you’re capable of. For example, if you want to move into web design as a career, you could start by building websites for friends or local nonprofits.
Even spending just five hours a week on these projects can add up to 250+ hours of experience in a year, which can easily build a solid portfolio that gives you the confidence to apply for roles in your new field.
If freelancing is part of the path you’re considering, these guides break it down even further:
Reframe your existing work as transferable experience
You’re not starting from scratch when you choose to switch careers. Chances are, you’ve already built a foundation of valuable skills in your current role that you can carry over into your next one.
Look for transferable skills that align with your target career. For example, a teacher moving into project management can point to experience in juggling complex timelines, coordinating with multiple stakeholders, and adjusting plans based on feedback.
Even if the end goal is different, core skills like problem-solving, communication, project management, or data analysis often apply across industries. That means your experience still matters; it just needs the right framing.
Start by listing your current responsibilities, then translate them into language that fits your new field. This simple “skills translation” step can make all the difference in a successful career change.
Keep a running skill journal
Once you decide to pursue a specific role, commit to learning new skills and track your progress along the way. Document all the new skills you’re developing through courses, side projects, and volunteer work. This ongoing record helps you identify patterns in what you enjoy and where you excel.
Plus, even small projects count as real experience that you can highlight in applications and interviews. Having this documented advantage sets you apart from candidates with no relevant background at all.
Step 4: Talk to People, Not Just Job Boards
The best way to seek out opportunities is not just quietly applying for jobs, but rather, it’s making genuine connections.
Reach out for low-stakes conversations (no pitching)
Most valuable opportunities come through personal connections, not online applications.
Instead of hardselling yourself, reach out to people in your target industry. You can send them a simple message like: “I noticed you’ve been working in [field] for several years, and I’m curious about transitioning into this area. Would you be open to a 15-minute chat about your experience? No pressure at all.”
If they agree, do your homework to make the conversation worthwhile. Prepare three to five thoughtful questions about their day-to-day work, career path, or industry trends, rather than just asking about job openings. Afterward, follow up with genuine appreciation and share something you learned or acted on from the conversation. These small steps build meaningful relationships and keep the door open for future opportunities.
If you’re ready to ask for a job, here’s a guide on how to ask for a job professionally without coming across too strong.
Grow your network in the relevant industry
After your initial outreach, use each conversation to grow your network. You can ask, “Is there anyone else you think I should talk to to learn more about this field?”
This approach helps you connect with a variety of people and gain diverse perspectives. Pay attention to recurring themes in these discussions. For example, if several people mention the same skill gap you might need to fill, that’s an important insight you need to take into consideration.
With every conversation, this natural network expansion brings you closer to your target role.
Opportunities don’t float, they’re attached to people
Many jobs get filled through word of mouth and personal recommendations before they ever appear online. The person who appreciated your thoughtful questions could remember you when a position opens up.
When changing careers, focus on building genuine relationships. This approach not only gives you deeper insights but also opens doors to more valuable opportunities, instead of just blindly submitting online applications and hoping for the best.
Step 5: Make a Strategic Decision
Now that you’ve gained experience and insights from peers in the industry, use these frameworks to guide your next move toward the career you want.
Reverse engineering: Study the why, not just the what
Look at the career paths of people you admire to understand how they reached their goals. The real value comes from knowing why they made certain choices, rather than simply copying their exact steps.
It’s important to ask yourself tough questions like, “When does it make sense to take a pay cut?” or “How do you know when it’s time to leave a company?”
By clarifying the real reasons behind your desire to change careers, you can move forward with greater confidence.
Yes and Yes: Stop thinking in false choices
We often fall into the trap of false either-or scenarios, like “Should I make more money or have a better work-life balance?”
Top performers find ways to have both. Instead of settling for one or the other, challenge yourself to discover creative solutions that offer the best of both worlds. You might not check every single box, but you can at least give it your best shot to build a career that brings purpose while moving toward the life you want.
Regret minimization: Zoom out and imagine the long game
When facing big decisions, think about what you’ll regret least looking back years from now.
Jeff Bezos used this approach when he left a stable Wall Street job to start Amazon. He asked himself whether he would regret not trying more than he would regret failing.
Consider if the safety of staying where you are might eventually feel like settling, while taking a risk could lead to important growth. Often, short-term discomfort paves the way for long-term satisfaction when you’re working toward something meaningful.
Step 6: Create a Resume That Tells a Story
Now that you’ve decided to take action, your resume becomes one of the most important tools to help you land a job in your dream career.
Lead with what matters to the job, not just listing down everything
Your resume should clearly explain why your background makes you a great fit for your new career direction.
Many people think resumes must follow a strict chronological order. Instead, focus on making your resume as relevant as possible so the hiring manager quickly sees why you are the right candidate. Lead with your most relevant experience for the target role, even if it isn’t your most recent job.
After reading your resume, hiring managers should remember one key thing that sets you apart and gives you an advantage over other candidates. This clear distinction makes you more memorable and increases your chances of moving forward in the hiring process.
To craft an outstanding resume, check out my guide on 20 skills to put on a resume, along with a proven winning resume you can use as a reference to build your own.
Highlight results, projects, and relevant overlaps
When crafting your resume, focus on showcasing your achievements and measurable results instead of merely listing job duties. Hiring managers look for proof that you can solve their problems, so concrete examples backed by numbers demonstrate your impact beyond just completing tasks.
For example, rather than saying “Responsible for social media accounts,” try: “Grew Instagram following from 2,000 to 10,000 followers in six months, boosting customer engagement by 35%.”
Be sure to highlight specific projects that showcase skills relevant to your target role. You want hiring managers to immediately see how your past experience connects to the job you’re applying for—don’t leave them guessing about your fit.
Step 7: Start Applying Before You Feel Fully Ready
Applying for jobs can feel intimidating, especially when you’re making a big career change. But waiting until you feel completely ready often means delaying progress. At some point, you need to take action and put your plans into motion.
Let momentum replace perfectionism: Refine as you go
Your first applications and interviews won’t be perfect, and that’s okay. Each experience provides valuable feedback to help you refine your approach. You’ll also gain practice and build confidence along the way.
The only way to get better at job searching is by taking action, learning from real-world feedback, and continuously refining your strategy. If you wait for everything to be perfect before starting, it might never happen.
So just begin even if you don’t feel fully ready yet.
Why Career Change Feels So Hard (Even When You Really Want It)
Making a career shift can feel paralyzing, even when you know it’s the right move. For many people, it’s not a lack of desire, but the weight of uncertainty, fear of failure, and the emotional labor of change that makes taking the leap so difficult.
In my podcast episode with Kara and Sean, we explored this exact tension. Sean has been in the same role for nearly a decade and is well aware that he’s hit a ceiling, both in growth and salary. And yet, even as Kara feels the strain of being the main breadwinner and burnout starts to creep in, Sean struggles to take the next step.
| Sean: [00:19:28] With my particular role, eight, nine years that I’ve been doing it, I am getting to a burnout point as well like Kara described. And so I have quietly applied for other positions pretty much annually, sometimes semi-annually, depending on what comes up, and I just haven’t gotten anything else. So those are all applications to similar roles, just in different places that would pay a little bit more. So she’s right, short of a total career shift. Unless some of those jobs start calling me back, I don’t have a huge potential for a salary increase, so butting up against the glass ceiling. Kara: [00:21:09] I’m the one who is looking for these jobs for him, which makes me sound like a crazy person, like a crazy wife. But I’m just so desperate to know that there’s something more waiting for us and that I can finally relax. Sean: [00:21:34] I don’t agree with that totally. She has been great about being proactive and sharing things that she finds on little Glassdoor, recommendations, or whatever. But I have my own alerts set up, and I apply for those too. It’s just, I think, probably time for me to decide whether I want to commit to shifting careers entirely, or– Kara: [00:21:59] Yeah, but I feel like I have to be the force to do it. |
This kind of struggle is something many people face when considering a career change. Here are a few possible reasons you find it hard to make the shift.
You don’t know what’s next, so you freeze
The uncertainty of a new path can feel overwhelming, especially when compared to the comfort and familiarity of your current role. This fear of the unknown stops many people from taking even the smallest step toward change.
To move past this paralysis, try breaking the process into smaller, manageable actions like the steps I shared above. When the path feels more concrete, taking the next step becomes far less intimidating.
You feel like you’re “starting over”
Making a complete career shift can feel like starting from zero. It’s common to experience a sense of loss, whether it’s letting go of your status, income, seniority, or the expertise you’ve spent years building.
But in reality, you’re not starting over. You’re bringing a wealth of experience, perspective, and transferable skills from your previous roles. Your unique background can actually set you apart from traditional candidates, offering fresh ways to solve problems and drive results.
Rather than seeing this as a restart, view it as another progressive chapter in your ongoing career journey.
Your identity is tied to your current role
After years in the same field, it’s natural to connect your sense of self with your job title or industry. Leaving familiar work means rethinking part of your identity, which can feel threatening.
But you are more than your job title. When you start seeing yourself as a dynamic, evolving person rather than someone fixed to one profession, you open the door to new opportunities. Shifting this mindset gives you the freedom and space for professional growth, aligning with the person you want to be.
Shift Your Mindset Before You Make a Career Move
Think of your career as a series of experiments, not one fixed decision. Each role offers valuable lessons about your skills, interests, and what truly matters to you.
When transitioning into a new role, embrace the mindset of a learner rather than an expert. This perspective opens you up to new possibilities and eases the pressure to be perfect right away.
Remember, feeling uncomfortable is a natural part of learning. It’s a sign that you’re growing, not failing.
How To Change Careers: What a Successful Career Change Looks Like
Real career changes rarely happen overnight or in a single giant leap. But with thoughtful, steady progress, you can take the necessary steps to make a rewarding career shift.
It usually doesn’t follow a straight line
Most successful career transitions involve a series of stepping stones, such as taking on side projects to build new skills, going through dedicated learning phases to deepen your knowledge, and holding bridge jobs that help you gain relevant experience.
While you’re in the middle of this process, the path can feel uncertain and messy, with progress that isn’t always linear. However, when you reflect on your journey later, you’ll often see how each step connected and contributed to your growth, making the bigger picture worthwhile.
Your first “win” might just be clarity
Sometimes, the most significant victory isn’t landing the new job right away, but just clarifying what you want and the direction you’re heading. Small milestones like completing a relevant course or making a valuable new connection count as meaningful progress toward this transition that deserves to be acknowledged and celebrated.
Even if you haven’t yet secured your dream job immediately, having the clarity and knowing what you’re working toward can act as a solid foundation for making intentional career choices. These choices can better align with your vision of a Rich Life—one where your work supports the lifestyle, impact, and experiences that matter most to you.
If you want to explore this idea further, check out my article, How to Live a Rich Life to start shaping your own path today.
