How to Escape the Trap of the Career Dead End—Without Going Back to School
A version of this article previously appeared on Skillcrush, an online education program for creatives, thinkers, and makers that gives total tech newbies the tools to make major career changes.
Scott Morris, Skillcrush
Face it: there's almost nothing worse than the looming feeling of a career dead-end. Every fiber of your being is telling you there's no future in your current situation, but with a full calendar, getting a new job seems easier said than done—especially if you're looking at a full-blown career change. Who has four or more years to spend getting a new degree or certification, much less the money to spend on another round of student loans?
I reached out to a group of career coaching professionals to get their take on career upskilling without another degree. Is there any way to leave a dead-end job without going back to school? The short answer— "yes!" It's not only possible, but practical, too. Read on to hear what these pros had to say about taking on a career transition‚—minus the crushing debt or debilitating classroom hours.
Before You Resign, Try to Save
When it feels like your job or career is hitting a dead-end, the first thing you should do is assess whether or not it's salvageable, says Andy Chan, founder at career coaching center Prime Opt. Rather than jumping into the job market immediately, Chan suggests talking to a manager about making a change to your current duties. It doesn't mean telling your manager you hope to leave your job—the goal is to see whether they can offer you new tasks in your current position, or whether they might even be able to put you in a new role on the same team. If it isn't possible to come up with an acceptable solution after transparent conversations with your supervisors, that's when it might be time to look elsewhere. Ultimately, Chan says to think about the future development of your career path and ask yourself, "Does my career path have a ceiling? Is my current position limiting where I can go, career-wise?" If your answers are "yes," Chan says it might be time to start considering a new job or an industry change.
Commit to How Awesome You Are
If it's truly time to move on, and you're hoping to escape a dead end job without the cost and time burden of more college, career coach Carlota Zimmerman says it's important to realize there's no one-size-fits-all-secret. "I've had clients who've gotten new jobs through LinkedIn, others who were introduced to a company that was hiring by someone in their knitting circle, and still others who got an interview after talking to a fellow college alum at their alumni association Christmas party," Zimmerman says. "Commit to the process, commit to the belief that you deserve a job you love, commit to the belief that you have something to contribute. Commit!" she says. Zimmerman adds that this is particularly crucial if you've been in a dead-end, depressing job for years. "It's akin to being in an abusive relationship," she says. "You have to learn—all over again,—to believe in yourself and your abilities. The worst thing you can do is half-heartedly attend one networking group, speak to no one, and go home deciding, 'Oh well, I guess my boss is right, I'm a loser.'"
If you're in a toxic workplace where you aren't getting the encouragement, challenges, and opportunities you need to be happy and fulfilled, it's easy to overlook just how draining that unhappiness can be. Before formulating the specifics of your plan for career change, it's important to take some time, reorient your perspective, and go all-in on the commitment Zimmerman describes. Your dead-end job may have sapped your enthusiasm a long time ago. Recapturing your drive and reframing your self-worth is the first step toward something better.
Up Skill on Your Lunch Hour
Once you've kicked the tires on your commitment to career change and reoriented your POV to one where you KNOW you deserve a better job, it's time to take practical steps toward making that job a reality. You might have put off career change in the past due to the fear that a lack of relevant degrees would make your transition impossible, but Career Counselor Rebecca Beaton says that—despite the myth of degrees being a barrier to entry—today's employers are less interested in whether or not applicants have x or y degrees, and are more focused on skills specific to the roles they're trying to fill.
What's more, Beaton says that plenty of skills necessary for either entering a new career or improving your marketability in your current one, don't require a fortune and excessive amounts of time, to acquire. Skills like programming languages, spoken languages, software suites, and management techniques can all be learned at your own pace during chunks of downtime—say, during your lunch break, or while you're waiting for a dentist appointment.
According to Beaton, once you have a general idea of what you want your new job or career to be, then it's time to review online job postings and learn what specific skills are required for that line of work. After you identify the skills you need, Beaton says there are thousands of free or cheap online courses that can be found through sites like Udemy, Coursera, EdX, or Pluralsight. Online courses like these will give you a good foundation in the skills you're interested in learning, but Beaton says they'll also serve to give you a better idea of your fit within a particular career path.
"If you thought you wanted to become a web developer but took a coding course and hated it, you might want to consider a different avenue," says Beaton. However, if you love your coding class, you can take it a step further and invest in something like an online 3-month bootcamp program. After you've taken a course or two and decided you're on the right path, Beaton says the best way to solidify those skills and generate experience for your resume is to do some actual work for a client using the skills you've been learning. "Find someone you can work for, probably at either a reduced rate or for free," says Beaton. "It's a great way to start building your portfolio."
Through this process of researching job listings, building on your skillset, and putting those skills to work in practical situations, you'll be firmly on the road to career change, sans massive student debt and four or more years of your life spent languishing in classrooms.
Don't Be Shy
Developing relevant skills is a big part of career change, but those skills won't do you much good in a vacuum—making connections in the industry you're hoping to break into is just as important. Valerie Streif, Senior Advisor at Mentat, a San Francisco-based organization for job-seekers, recommends setting up informational interviews with people working at the kinds of jobs you're interested in. That way, you'll be networking and meeting potential future colleagues while learning more about the skills you need to sharpen as you make your career move.
Streif says the best approach is to send a warm outreach email to your interview prospect and ask if you can take them to lunch. If you're at a loss for who to reach out to, talk to any current industry connections or acquaintances you have and see who they can put you in contact with. Then, Streif says, when the meeting happens, take notes and make sure not to be too pushy or to outright ask your interviewee to help you get a job. Focus on listening, gathering information, and establishing a connection with your interviewee as a future professional contact.
Resume Coach Robyn L. Coburn says that attending industry-specific networking events is also a must when laying the foundation for a career change. Sites like Meetup, Eventbrite, and Eventful are good places to start searching for relevant events in your area. While Coburn knows that networking feels daunting at first (and for some people, it never stops being scary), the key to making it easier is preparation. "Instead of thinking of networking as a job interview, think of it as a fact-finding mission," Coburn says.
Coburn also suggests preparing two or three questions about the job or company you're interested in that require more than a "yes" or "no" answer, and to be ready to ask the people you meet. Much like an informational interview, this is a chance to listen, get better insight into your career of interest, and start getting to know people in the field. And remember, you don't have to speak to the CEO of a company you want to work for, in order for a networking event to be successful. Coburn says that simply connecting with one new person who works in the field is enough to make the effort worthwhile.
Don't Sell Yourself Short
So you're building skills in your downtime, and making connections to learn more about the industry you want to break into, but when you're ready to make that final leap you'll need to package yourself in a way that stands out to potential employers. What can you do to polish off your resume and market yourself in the best way possible?
Streif says DO fill your resume with transferable skills—anything relevant you have previous experience with, alongside any skills you've familiarized yourself with in preparation for changing jobs—but DON'T add fluff.
"This is something so many people struggle with, and doing it incorrectly won't help your chances of making a career move," says Streif. "Trying to make up for a lack of experience with excessive, meaningless words like 'effective communicator' or 'team player' isn't going to fool anyone. You need to be creative, think of the SPECIFIC projects you've completed in your current role, and brainstorm how those responsibilities transfer into a different role or how they'd help you complete tasks in a new one. Specificity is key!"
Beaton says that your resume is also a great place to circle back and present any test work you've done while building your skills, even if you did it for free. "The fact that you worked for free or cheap isn't relevant to the employer," says Beaton, "the main thing is that you have the right skills and you know how to use them. Beaton says it's also important to include the results you achieved for your client (or employer) using those skills. For example, if you took a course to learn Search Engine Optimization (SEO) and did some free SEO work for a friend, you might put something like 'Optimized full five-page website, resulting in a 200% increase in traffic and website appearing on the first page of Google for two primary keywords."
Marketing yourself effectively is as important as any aspect of your job search, so don't sell yourself short—everything relevant to your future job counts, and it's up to you to advertise it proudly.
Leave on a High Note
Finally, Coburn cautions, never complain about your current job or company during your transition process. "If you are asked why you want to move on," says Coburn, "express your reasons in terms of your own growth or needs, rather than due to not liking your company. Coburn suggest the approach of, "It's been a great place to work, but I've reached as far as I can go there and I want to make a contribution in a larger organization with more opportunity to advance," or, "It's been a great place to learn about the industry from an industry leader, but I'd like to find a smaller company where my skills and experience will make a difference in the day-to-day operations," depending on the type of company you're applying for.
Maintaining a positive relationship with your current job while you work toward a career change is also critical, Coburn says, because it's important not to leave a job you have without securing your financial situation and—hopefully—your next position.
"Remember," says Coburn, "the currently employed person is always more attractive to employers than someone who is out of work." By the same token, Coburn says not to accept a new job offer out of desperation—a surefire way to end up in another unsatisfying employment situation. Instead, take your time and really consider any new job opportunities that come your way—how will it address your current job unhappiness and how will it help you grow your career moving forward? When the right job comes you'll know it, and—through upskilling, networking, a solid resume, and a positive commitment to change—you'll be in a prime position to make your move.
💎Want to know what engineering teams are like at Workiva? Watch the video to the end to find out!
📼 Engineering teams at Workiva are constantly hiring. Marie Yue, Senior Engineering Manager at the company, tells you what they look for in a candidate and what the dynamics of teamwork are like.
📼 The typical path in the engineering teams at Workiva is that you grow into a senior, and then you move into a lead role. From there, there are a few different tracks that you can take depending on your interest. You can become a staff engineer, an architect, or even an engineering manager. What are you waiting for to apply?
📼In the engineering teams at Workiva every member should feel empowered to do their job effectively. For this, each has to understand how the work they do day to day solves customers’ problems. Managers will always seek to be aware of members’ career path aspirations so that they can look for opportunities and projects to help each person reach the next step in their career.
Engineering Teams At Workiva: A Safe Space
Marie Yue’s team is a safe space for people to make mistakes and ask for help, and each member feels a sense of belonging and inclusion. She wants to make sure that everyone is individually empowered to lead and make decisions. For this, the team has regular meetings where they do fun things like play virtual games or eat lunch together, and they also like to re-review and add to their team working agreement once a quarter.
🧑💼 Are you interested in joining Workiva? They have open positions! To learn more, click here.
Get to Know Marie Yue
If you are interested in a career at Workiva, you can connect with Marie Yue on LinkedIn. Don’t forget to mention this video!
More About Workiva
Workiva was founded to transform the way people manage and report business data with various collaborators, data sources, documents, and spreadsheets. Today, people all over the world use their platform to seamlessly orchestrate data among their systems and applications for transparent and trusted connected reporting and compliance. At Workiva, they are innovative in everything they do—from how they build their software, to how they serve their customers, to how they treat their employees.
We all have our favorite websites– the ones we frequent, bookmark, and recommend to others. You might even enjoy some website features so much that you’ve found yourself wondering why they aren’t more popular. Or maybe you’ve experienced times where you were frustrated with a website and wished you could add features or even design your own!
If you’ve ever found yourself intrigued at the prospect of designing and developing your own websites, then a career as a web developer might be just for you!
As a web developer you would be responsible for coding, designing, optimizing, and maintaining websites. Today, there are over 1.7 billion websites in the world and, in turn, the demand for web developers is on the rise. In order to figure out what kind of web development work best suits you let’s start with an introduction to the three main roles in web development that you can choose from.
The Three Types of Web Development Jobs
Front-End Web Development: The Creative Side
In addition to programming skills, front-end developers need to be detail oriented, creative, willing to keep up with the latest trends in web development, cyber security conscious, and geared toward user-friendly designs. The median salary for a front-end developer can reach well into the $90,000 to $100,000 range.
Back-End Web Development: The Logical Counterpart
While a house can be beautifully decorated, it’s incomplete without a solid foundation and efficient infrastructure. Similarly, a well-designed website depends on logical and functional code to power the features of that website. Back-end web development is code-heavy and focused on the specifics of how a website works. If you enjoy the analytical challenge of creating the behind-the-scenes code that powers a website, then back-end development is for you.
Full-Stack Web Development: A Little Bit of Everything
A full-stack developer is essentially the Jack (or Jill)-of-all-trades in web development. Full-stack developers need to be knowledgeable about both front-end and back-end roles. This does not necessarily imply that you would need to be an expert in both roles, but you should fully understand the different applications and synergies they each imply. In order to work in this position, you will need to know the programming languages used by front-end and back-end developers. In addition to these languages, full-stack developers also specialize in databases, storage, HTTP, REST, and web architecture.
Full-stack developers are often required to act as liaisons between front-end and back-end developers. Full-stack developers need to be both problem solvers and great communicators. The end goal for a full-stack developer is to ensure that the user’s experience is seamless, both on the front-end and on the back-end. In return, you can expect to earn a median salary of $100,000 – $115,000 a year for this role.
Taking the Next Step
Web development is both in-demand and lucrative! All three roles described above contribute to specific aspects of web development and the scope of each one can be customized to the industries and positions you feel best suit you. Regardless of which role you choose, all of them need a foundation in programming.
To gain the programming skills needed in each role, you can enroll in courses or learn independently. Coding bootcamps are a great way to boost your skillset quickly and efficiently.
Click here for some of our highly rated programming bootcamp options! Make sure to check out the discounts available to PowerToFly members.
Joseph Arquillo doesn’t work in Human Resources — he works in People Operations. And the distinction matters.
“It was named ‘human resources’ because it saw humans as resources, utilized for certain tasks or behaviors. But that’s not really what it’s about,” says Joseph, who is a Senior Manager of People Ops at Clyde.
“Calling it ‘people ops’ adds back what you lose with ‘HR.’ My philosophy is that I am there to support you. I am there to work with you, empower you, and enable you so you can be your best self.”
For Joseph, a key element of helping employees become their best selves is making sure that the workplace, whether in-person or virtual, is an inclusive space for all. That doesn’t happen by accident — it requires a dedicated DEIB strategy and leaders who are committed to asking hard questions of themselves and others.
We sat down with Joseph to hear more about his professional journey, and the practices of leaders who create environments where everyone feels included.
More Than Just a Number
As a college freshman, Joseph planned on sticking with liberal arts when it came to choosing a major. But then he took a class in Boston College’s School of Education, and loved its holistic approach to applied psychology.
This inspired him to switch his major to psychology and human development, and select minors in political science, and management and leadership, where he enjoyed learning about organizational psychology.
After graduation, he explored the consulting space to put theory into practice, but found out during an internship at a multinational consulting firm that finance or accounting weren’t the places he wanted to build his career.
“Since Big Four companies have 250,000 employees, you become just a number,” he says of the experience. “It wasn’t my cup of tea. Too corporatized.”
That kicked off Joseph’s interest in startups.
“It’s always fun to get in the weeds! One thing that’s very interesting to me is a challenge,” he says. “When you’re helping a company like Clyde grow and scale, joining when they’re at a Series B and helping them get to the next level, you really get to focus on the interaction between people, process, and product,” explains Joseph. “You need to hire the right people to work towards increasing efficiencies in all areas, but also make sure that we’re enabling them to create a strong product.”
6 Keys To Building Inclusive Spaces as a Leader
Across the different industries and companies that Joseph has worked in, he’s identified the behaviors that create truly inclusive environments — as well as those that discourage them.
Here’s what he’s seen:
- First, recognize your own privilege. “If you’re a man, you have privilege, even if you’re a gay male. If you are a white woman, you have racial privilege. It’s really important that you’re cognizant while you interact with somebody how they might interpret the interaction based on your identity.”
- Leaders should always speak last. This is important always, but especially in in-person spaces, where it might seem even more nerve-wracking to speak up in a crowd, says Joseph. “You want to make sure you’re creating that space for employees who aren’t as senior to feel comfortable voicing their thoughts.”
- And, leaders should use check-ins liberally. “You need to ask yourself how you’re supporting your employees. Are you checking in on them as people before you ask about certain tasks? You want to foster a workplace where employees from all walks of life can feel supported,” he says.
- DEIB isn’t just about adding new initiatives — sometimes it’s about removing barriers. “You need to remove unnecessary bias,” explains Joseph. “That can mean making sure you have appropriate policies and practices that don’t hinder people depending on who they are or where they live.”
- Maximizing participation requires planning with a diversity lens. Joseph has helped the Clyde team gather together and bond as a group. Along the way, he’s been careful to consider physical and psychological safety for everyone involved. “For instance, if you’re doing an event, do you have someone who’s not drinking? Have you set up the environment for people who might have a physical disability, or carefully planned the flow of activities for people who might be neurodivergent?”
- Saying you want to be better isn’t enough — articulate actions you will take. “Pride is a great example,” explains Joseph. “Yes, June is a time to celebrate. But it’s also a time to march. And beyond that, how do you show up and celebrate with the LGBTQIA+ community throughout the year?”
Embracing the Unknown
If you visit Joseph’s LinkedIn profile, you’ll see his personal motto: “Without challenge, change, and a bunch of unknowns, it’s no fun.”
That belief has led him to study what he’s passionate about, to take on new and exciting roles at growing startups, and now, at Clyde, to help formalize what world-class people operations looks like at a fast-growing company.
“I view myself as a connector that really empowers people, challenges teams, and helps drive us towards what I consider to be an improved future,” he says. “I feel like it’s my responsibility to be the chief advocate for each of our employees, and remove any barriers in the way of their growth.”
Insight from SoftwareONE’s Jeff Cannon and Chris Lecosia
SoftwareONE’s Jeff Cannon Business Development Executive US) and Christopher Lecosia (Senior Consultant) share a similar adventurous and brave spirit, which has led to a long trajectory of creative experiences for both of them. From taking care of two new puppies to backpacking across Europe — neither of them back down from a challenge.
As members of the LGBTQIA+ community, Jeff and Chris spent a large portion of their careers fighting for inclusive workplaces where they feel a sense of belonging, and opportunities to use their experiences to serve people, no matter what career stage they’re in. And they’ve both recently found that in the global provider of end-to-end software and cloud technology solutions SoftwareONE.
We sat down with Jeff and Chris to hear their stories on how they navigated mid and late career changes and their journey to finding a company where they felt valued. Keep reading to the end for four major tips on how to successfully pivot careers.
The Journey to SoftwareONE
Jeff Cannon was born in Tacoma, Washington, but considers both Texas and Georgeia his home. After graduating from college with a bachelor's degree in English and History, “I wanted to go to graduate school for history,” he explains. But upon arrival, he realized graduate school was not the right path for him, so he packed his backpack and set out for a trip through Europe instead.
This adventurous spirit led him back home to pursue exciting challenges, such as opening a hotel in Austin, working as a flight attendant in New York and Hawaii, and eventually pursuing a sales career at Dell. “I was an account executive for large university systems and large K-12 systems providing information technology to students to be able to further their education. It really fit in with my mantra around how important education is in society,” Jeff explains.”It's kind of my thing.” But after nearly 20 years at the company, he decided to look for new opportunities. “I was tired of doing the same thing all the time.” Enter SoftwareONE.
“This was an opportunity to do something completely different and take the information that I learned and use it to help build a practice that can accomplish some of the same things,” Jeff explains. He joined the company as a Business Development Executive Executive where he works to build the company’s education practice within the public sector in the United States.
SoftwareONE is a company where Jeff can thrive professionally and personally. He specifically cites the company to be people-first, which his coworker Christopher Lecosia agrees with. “SoftwareONE is a place where you can thrive as an employee, and where your creativity can flourish,” says Chris.
SoftwareONE is a leading global provider of end-to-end software and cloud technology solutions, with headquarters in Switzerland. The company itself prioritizes people as their “greatest asset” and advocates for life-work harmony. Their company’s core values are Employee Satisfaction, Customer Focused, Speed, Passionate, Integrity, Humble and Discipline, to name a few, and they ensure that they have “a welcoming – and constantly evolving – work environment for all”, no matter the racial, ethnic, religious, sexual or other preferences.
Christopher works as Senior Consultant for SoftwareONE. He entered the field of IT in 1974. “Back then it was called data processing,” he jokes. “But I kind of fell into IT consulting.” He enrolled in college as an accounting major, but quickly realized that was not the path for him. “I drove into the parking lot of this college for the first day and I got very scared,” explains Chris. “I turned around and went home and I found a job.” And he was able to pursue jobs that allowed him room to change and grow with the market. He began as a systems programer and, progressively, he scaled to managerial data processing roles at multiple software companies, including IBM. He played a key role in leading and growing software asset management programs, directing support for configuration and asset management, and serving as a senior project manager for multiple teams in his previous companies.
His successful 40+ year-long career led to the start of a well-deserved retirement. “I turned 65 last October, and I thought, ‘okay, I think I’ve had enough,’ and I decided to retire in full.” But his retirement was short-lived. “A few months before I retired, [my company] had put out an RFP to the street, which SoftwareONE responded to, and I'll never forget,” says Chris. “I was hearing them respond to me and I thought, ‘Wow, these people know what they're talking about. They're really sharp and I really believed in the value that they could bring.’” So when he was offered a position as a Senior Consultant, he didn’t think twice about coming out of retirement. “In November, a recruiter from SoftwareONE called, and I started in January of 2022.”
Changing jobs after working for a company long-term can be risky, especially later in your career. But both Jeff and Chris agree that the benefits of working at a company like SoftwareONE are well worth the risk. And for the first time, they’ve felt like they can show up as their full, authentic selves at work.
Jeff recalls past workplaces that, when push came to shove, “had an undercurrent of non-acceptance.” This undercurrent brought many challenges, but he credits them for his confidence today. “I have no issues whatsoever showing up originally as myself. And at SoftwareONE, everybody's been really lovely.” Even remotely, he finds ways to connect with his coworkers, and he feels like he can do so authentically.
Chris reiterates this in his own trajectory at SoftwareONE. “When I started, my Regional VP asked me for a bio. In my bio, I talked about my husband and my two dogs and how long we've been together. That got sent out to everybody in the organization. So when I onboarded, everybody already knew,” he explains. “It was the first time in 65 years that, right from the get go, there was no pretense at all as to being something different than I am. And that's how I came out at SoftwareONE. It was good to do that. I feel truly authentic.”
Advice for Mid-Career Pivoters
Both Jeff and Chris have successfully pivoted roles and companies later in their careers. They offer four tips to consider before making the jump to a new role or joining a new company.
1. Find a place that values service to the client. “Have the mindset of service,” says Chris. “ I'm a service oriented person and part of being of service is to share my experience, strengths, and hope with other people. Whether that's on a, social, spiritual, mental level, or on a professional technical level, this helps bring growth to you, and to the company you’ll work for.” Jeff shares that, “with this mindset, we see the challenges that customers face, so we're able to better articulate to customers what our value proposition is. We can help clients achieve their goals, and everything comes a lot more easily and naturally.”
2. Believe in what you have to offer. Chris and Jeff share that aligning with the company’s mission is another key aspect to consider before changing companies. “I never thought that anybody would want to hire me at 65 years old,” Chris shares. “I had been in my former job where I saw many opportunities that I thought I was perfect for, in terms of advancement, but I wasn't given those opportunities because of my age. I started to feel dried up a little bit. When I got the offer at SoftwareONE, I felt I really wanted to come back, be of service, keep my brain sharp, and do something. I do believe I have something to offer to many clients, as well as colleagues. And that's what made me make the move.”
3. Think of the experiences you bring to the table. Jeff shares how he transferred his knowledge to his new role. “I was able to take everything that I had learned about building an organization and bring it over to a company that needed that expertise specific to the United States. Being able to have the opportunity to do some of that background work and build on alliances has been, and continues to be, a great opportunity.”
4. Find a workplace that prioritizes diversity. “Each one of us brings a certain set of characteristics with us that sit well with our clients,” explains Chris. “The diversity we bring to the company — whether it be age, gender, color, educational background, intellectual capacity — all of that color makes us more relatable to our clients and our customers.” This leads to the company’s overall success.
SoftwareONE is constantly looking for dynamic employees like Chris and Jeff. Check out their company page to find out more about their roles!