What does it take to build a fulfilling career in today's job market? There's no single answer. For some professionals, it's finding more flexibility or new ways to use their skills. For others, it's pursuing work that aligns with their values or knowing when it's time to make a change.
In Good Job!, a new video series from Robert Half and Hanna Goefft of Hanna Gets Hired, career experts, entrepreneurs and professionals share their experiences navigating career decisions, overcoming setbacks and finding opportunities for growth.
Each conversation offers a different perspective on what makes a good job and practical advice for building a career that works for you.
Here are some of the career lessons from the series so far.
How to build a career that works for you: Lessons from Good Job!
How to build a portfolio career using the skills you already have
Could your existing skills and experience help you earn income in more than one way? A portfolio career offers an alternative to relying on a single full-time position, but building one takes planning, persistence and a willingness to adapt.
In the first episode of Good Job!, Hanna speaks with Anna Mackenzie, a U.K.-based startup advisor, mentor and author of Anna Mack's Stack, about her unconventional path to a six-figure portfolio career.
Anna describes her career journey as "ultra-squiggly," spanning consulting, mentoring, digital products, writing and education. Along the way, she's navigated setbacks, including a period when her business revenue dropped to zero.
Her experience highlights the opportunities and challenges of self-employment, including how to turn professional experience into services that clients are willing to pay for.
Two ideas to consider for your own career:
Identify skills you can offer in different ways. Think about the knowledge and experience you've developed throughout your career. Could those skills translate into consulting, freelance projects, teaching or other professional services? Start by identifying a specific problem you could help someone solve.Build and test before making a major transition. Multiple income streams can offer flexibility, but they also require time to establish. Consider testing a service or taking on a small project before depending on it as a primary source of income.
Watch the full conversation with Anna Mackenzie: How to Build a 6-Figure Portfolio Career | Anna Mackenzie
Hannah GT: Welcome to Good Job, where we reverse engineer the careers you admire, one decision at a time. Today's guest is Anna McKenzie, startup adviser, portfolio career mentor, writer and educator.
Anna McKenzie: To me, a good job is one that provides autonomy and freedom. I want to choose who I work with, what problems I work on and when I work. Continuous learning and being surrounded by people who challenge me are also important.
The foundation of a portfolio career is diversification. Rather than relying on a single employer or business, a portfolio career is built around multiple income streams, opportunities, projects and clients. It creates flexibility but also comes with responsibility. The reality is that there can be a fine line between freedom and burnout.
After leaving what I considered a dream job to pursue a podcast business full time, the COVID-19 pandemic caused our sponsorship revenue to disappear almost overnight. That experience taught me the importance of maintaining an emergency fund and ensuring that one reliable income stream anchors a portfolio career.
For professionals considering this path, it is helpful to inventory your skills, experience and accomplishments. Many people underestimate the value they can bring outside of a traditional job description. Corporate experience, professional networks and specialized knowledge can often be translated into consulting, advisory, mentoring or other opportunities.
When developing offerings, pay attention to recurring problems and questions. Patterns often reveal opportunities to create services, products or educational resources. Building a portfolio career is an iterative process that evolves over time based on market demand and personal interests.
One of the most important lessons I've learned is to trust your instincts. There are many ways to build a fulfilling career, and success looks different for everyone. Understanding your priorities and remaining open to new opportunities can help create a career that provides both impact and flexibility.
Hannah GT: Thanks for joining us, Anna. For more career insights and conversations like this, subscribe to Good Job.
Thinking about quitting your job? Ask yourself these questions first
When you're unhappy at work, finding a new job can feel like the obvious next step. But before starting your search, it's worth considering what you want to change and whether a different role will actually address it.
In episode two of Good Job!, Hanna speaks with Sho Dewan, CEO and founder of career coaching platform WorkCap, about making more intentional career decisions.
Sho encourages professionals to look beyond job titles and compensation to consider what makes a role fulfilling. His approach focuses on understanding the work you enjoy, recognizing your strengths and identifying opportunities that better match your priorities.
That distinction can be especially important in a competitive job market, when pressure to find a new position may lead you to pursue opportunities that aren't the right fit.
Two ideas to consider before making your next career move:
Define what you're looking for beyond a new job title. Consider the responsibilities you enjoy, the work environment where you perform best and the priorities that matter most to you. Knowing what you want can help you evaluate opportunities more effectively, whether you’re searching independently or working with a recruiter on a career change.Assess whether a potential role addresses your reasons for leaving. If you're considering a change because of limited growth opportunities, for example, look closely at how a prospective employer supports career development. A new position may not be a better fit if it presents the same challenges.
Watch the full conversation with Sho Dewan: Don't Quit Before Asking Yourself These 3 Questions | Sho Dewan
Hannah GT: Welcome to Good Job, where we reverse engineer the careers you admire, one decision at a time. Today's guest is Sho Dewan, founder of Workhap, career coach, recruiter and author of Get Hired, Get Paid, Get Happy.
Sho Dewan: A good job is about more than salary or prestige. It comes down to three things: enjoying the work itself, enjoying the people you work with and enjoying the life the job allows you to have. When all three align, you're much more likely to feel fulfilled in your career.
Early in my career, I followed a traditional path into consulting because it seemed like the right choice on paper. Over time, I realized that financial success alone wasn't enough. I was drawn toward helping people, coaching others and guiding careers, which eventually led me into recruiting, human resources and career coaching.
Career fulfillment often requires experimentation. Many people stay in jobs that no longer fit because they are afraid to explore alternatives. Trying different industries, roles and experiences can help uncover what motivates you and where your strengths lie.
When I left my corporate career to build my business, I had only a small financial cushion and no guarantee of success. What kept me going was seeing gradual progress, believing in the value I could provide and having supportive people in my corner who encouraged me to keep moving forward.
For job seekers today, networking remains one of the most effective ways to create opportunities. Building relationships, staying connected and demonstrating how you can solve problems for employers often matters as much as submitting applications online.
I also encourage people to identify their personal "qualities of fulfillment" before beginning a job search. Understanding what matters most, whether that's flexibility, creativity, compensation, purpose or growth, can help guide better career decisions. Once you've defined those priorities, explore different possibilities before committing to a new direction.
Above all, don't be afraid to try something new. Careers rarely follow a straight path, and the process of exploring different opportunities often leads to the most rewarding outcomes.
Hannah GT: Thanks for joining us, Sho. For more career insights and conversations like this, subscribe to Good Job.
Turning a passion into a business takes more than enthusiasm
Pursuing a career built around something you love can be rewarding, but passion alone doesn't guarantee business success. Developing a sustainable business also requires planning, understanding your audience and being willing to adjust your approach over time.
In episode three of Good Job!, Hanna speaks with Gaby Dalkin, founder of What's Gaby Cooking, cookbook author and chef, about the work behind building a successful food business.
Gaby began sharing recipes on Blogspot while attending culinary school and spent years working as a private chef before growing her brand. Her experience illustrates how a business can develop gradually through experimentation, relationship-building and identifying new opportunities.
She also discusses the importance of knowing when to say no, negotiating for better opportunities and developing multiple income streams.
Two ideas to consider if you're interested in entrepreneurship:
Test whether there's demand for your idea. Before leaving your current position, consider ways to build experience, find potential customers and determine whether people are willing to pay for what you offer. Starting small can help you refine your approach while limiting financial risk.Look for opportunities to grow sustainably. Building a business doesn't mean pursuing every opportunity that comes along. Evaluate which projects support your long-term goals and where your time and expertise can deliver the most value.
Watch the full conversation with Gaby Dalkin: What Nobody Tells You About Being Your Own Boss | Gaby Dalkin
Hannah GT: Welcome to Good Job, where we reverse engineer the careers you admire, one decision at a time. Today's guest is Gaby Dalkin, founder and CEO of What's Gaby Cooking, a food, recipe and lifestyle brand that has grown from a personal blog into a multifaceted business.
Gaby Dalkin: A good job is something you're excited to do every day. For me, it's about building meaningful work, surrounding yourself with great people and creating a life that allows you to be present for the people who matter most.
While many people say to "follow your passion," that advice often leaves out the reality of what it takes to turn a passion into a career. Building a business requires long hours, constant effort and a willingness to take on many different responsibilities. When your hobby becomes your job, it can change your relationship with the thing you love.
After a marketing and public relations job ended during the 2008 recession, I enrolled in culinary school and began building experience as a private chef. At the same time, I started a food blog as a side project. For years, I worked on the blog nights and weekends while maintaining other sources of income until the business became financially sustainable.
One of the most important lessons I learned was the value of building gradually. Rather than immediately taking a big leap, I tested ideas, developed my audience and created multiple revenue streams before making the business my full-time career.
As the business grew, I became more intentional about defining my brand and understanding what aligned with my values. That meant turning down opportunities that didn't fit, even when they were financially attractive. Protecting audience trust ultimately proved more valuable than short-term gains.
Today, the business includes digital content, cookbooks, brand partnerships, consumer products, restaurants and live experiences. Growth has come from continually experimenting, listening closely to audience feedback and adapting when new opportunities emerge.
One of the biggest factors in my success has been learning to ask for what I want. Whether pursuing partnerships, launching products or exploring new ventures, opportunities rarely happen without taking initiative. If you don't ask, the answer is always no.
For anyone building a career or business, my advice is simple: start before you feel ready, stay open to learning and don't be afraid of rejection. Persistence, adaptability and confidence in your vision can open doors you never expected.
Hannah GT: Thanks for joining us, Gaby. For more career stories and insights, subscribe to Good Job.
Finding meaningful work when your career path isn't linear
No one's career path is perfect. Your experience across different roles can help you identify what matters to you and what you can offer a new employer.
In episode four of Good Job!, Hanna speaks with Miki Reynolds, a startup ecosystem builder and investor who took a 50% pay cut to pursue work she cared about. Their conversation examines what it means to build a career around a mission that matters to you, without necessarily sacrificing long-term ambition or earning potential.
Miki shares how she turned a broad professional background into what she calls a "Swiss Army knife" skill set, and how one cold email opened the door to an entirely new career direction.
Two ideas to consider for your own career:
Look beyond job titles for a sense of purpose. Mission-driven work extends beyond nonprofits. Consider the problems you want to help solve and the organizations working on them, then look for roles where your skills could contribute.Connect the dots in your experience. If your career has taken several turns, identify the transferable skills that link those roles. Explaining how those skills work together can help an employer understand the value of your background.
Watch the full conversation with Miki Reynolds: She Took a 50% Pay Cut to Do Work That Mattered | Miki Reynolds
Hannah GT: Welcome to Good Job, where we reverse engineer the careers you admire, one decision at a time. Today's guest is Miki Reynolds, startup ecosystem builder, investor and former CEO of Grid110.
Miki Reynolds: A good job is one that goes beyond compensation and titles. It's work that feels meaningful, creates impact and allows you to learn from people you admire. For me, fulfillment comes from contributing to something larger than myself and helping create opportunities for others.
Early in my career, I followed a traditional path and achieved many of the markers of professional success. I had the title, compensation and career progression I thought I wanted, but I realized I wasn't fulfilled by the work itself. That experience forced me to rethink what success really meant.
One of the most valuable lessons I've learned is the power of being a generalist. Working across industries, functions and roles gave me a broad perspective that helps me solve problems, adapt quickly and support founders from many different backgrounds. While I may not be the deepest expert in every area, understanding how different pieces fit together has become a significant advantage.
A major turning point came after being laid off during a company shutdown. Instead of rushing into the next role, I gave myself time to recover from burnout, explore new interests and connect with new communities. That period of uncertainty ultimately led to opportunities that shaped the rest of my career.
Through roles at General Assembly, Grid110 and Slawson & Co., I became increasingly focused on creating access for entrepreneurs and founders who have historically been overlooked. I learned that meaningful impact doesn't always come from a company's product. It can also come from creating opportunities, building inclusive communities and helping others succeed.
Community has been one of the most important factors in my career growth. Nearly every major opportunity I've had came through relationships, conversations, shared learning experiences and the willingness to reach out to people. Building connections, joining communities and creating spaces for collaboration can open doors that traditional job applications often cannot.
I've also learned that many of the best opportunities don't exist yet. Sometimes a role is created because you're willing to identify a need, suggest a solution and take initiative. Being curious, resourceful and willing to figure things out can be just as valuable as having the perfect credentials.
For anyone navigating career uncertainty, my advice is simple: don't be afraid to make a leap before you have every answer. You can learn along the way, adapt as circumstances change and often discover opportunities that weren't visible when you first started.
Hannah GT: Thanks for joining us, Miki. For more career insights and conversations like this, subscribe to Good Job.
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Whether you're considering a career change, exploring entrepreneurship or looking for greater fulfillment in your current role, the experiences shared in Good Job! offer different perspectives on navigating professional growth.
Watch the conversations and find more career advice by subscribing to the Robert Half YouTube channel.
