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Career and Interview Tips

How to Escape the Trap of the Career Dead End—Without Going Back to School

Partner Content

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.


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Work-Life Integration

The 13 Tools You Need to Work Healthier—Not Harder—and Get More Done

Partner Content

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.

Haele Wolfe, Skillcrush

What makes a great designer or developer? Is it the right credentials, education, or tools? Or is it something less tangible, like determination or a great sense of organization? Or maybe it's even simpler than that: Success in any field has a lot more to do with your daily work routine than you might think. And as the workweek shifts from the standard 40 (or 50, or 60) hours to something more closely resembling the natural fluctuations of our individual lives, our concept of how we work needs to shift, too.

Taking care of yourself is critical to a successful career: You can't expect to deliver top-quality work if you're constantly exhausted or sick. In that vein, I put together a list of habits and tools for busy tech pros (or really—any employee) to implement into their daily routines so that they can work not just harder, but healthier. There are cheap buys, splurges, and free hacks, but in any case: It's your health. Treat yourself.

Career and Interview Tips

What It’s Like to Go Back to Work After a Long Break

Partner Content

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

About a year ago I started to consider getting back into the workforce. I'd left unskilled retail work and a long, meandering college career 12 years earlier to be an at-home parent to my first daughter. A second daughter followed three years after that—so I'd had my hands full trying to keep up with them while my wife worked full-time—but at the ages of 12 and nine, my kids were getting to a point where they didn't need as much constant parental care. Meanwhile, my wife and I were looking for ways to add some savings for their college funds, and to have extra money set aside for emergencies.

The problem was, my parenting duties were still just enough to make the idea of working outside the home—even part time—fairly daunting. I remember thinking that if only there were a way to make money from home, that would be the perfect scenario—but the idea sounded like something out of a get rich quick scam. Fortunately, I told my woes to a friend of mine and she metaphorically slapped some sense into me about the very real, very achievable world of remote work. The company she worked for happened to be looking for part-time copywriting help, and within a couple of weeks of our first conversation, I found myself working for Skillcrush.

At the age of 40, I thought I'd run my course as far as what I was going to be doing with my life—I've never been a particularly ambitious or career-minded person, and I was perfectly happy with most aspects of being an at-home parent and husband. But, I did still feel like something was missing. It had been so many years since I'd really gone out on a limb and tried something new that there was a part of me that felt stagnant.

Paid work filled this void by adding a new dimension to my life, and—although I'm busier now than I've been in years—my life is fuller and more focused than it was before. I have to think about schedules and parcel out specific time for different activities in a more regimented way than I did before, and it makes me really think about how to spend my time and appreciate the downtime I have in between. It's also refreshing to learn and implement new skills—and actually earn a paycheck for doing so.

I'm Not a Barista Anymore: Fighting Impostor Syndrome

At first, I looked at my new job the same way as the bookstore and barista jobs I'd had decades prior: I figured I was supposed to be available, receive instruction on what to do, do what I was told, and rinse and repeat. I worried that asking for clarification or even requesting more work would be perceived as me not knowing what I was doing and expose the fact that I really didn't belong. But professional work isn't about clocking in and mindlessly following a set of instructions—you need to find or create opportunities to get actively involved in your workplace, particularly if you're freelancing or remote, where nobody actually sees you.

And, I needed to let go of my impostor syndrome. If I didn't belong, they wouldn't have asked me to be there—end of story. But I let that feeling take over, afraid of my own shadow, sitting quietly and not wanting to be noticed as opportunities passed me by.

With that approach, my hours dried up and I was exactly where I was before: stagnant. Luckily, a few other Skillcrushers were kind enough to clue me in on how things work. Asking questions? Not a bad thing. Requesting more hours and seeking out ways to evolve and define your role as a part-time freelancer? Also not a bad thing. Once I followed this advice, I started to hit my stride and establish a solid role in the company.

Here's what I wish I'd known when I started: Don't be afraid to express interest in projects you're not already attached to, or to let your managers or coworkers know about skills or interests you have that aren't typically part of your job title. Try saying something like "I hear that we're developing a podcast. I have some audio editing skills and I'd love to be a part of the project." Or, "I'd love to learn more about how we track our audience. May I sit in on the next numbers meeting and observe?" Nobody will think you're being pushy (my greatest fear). Remember that your colleagues and managers want you to succeed—and if they don't, you're working for the wrong company.

More Work is a Good Thing?

Beyond learning the culture of a workplace, I also had to adjust to an entirely new system of timing. During my first few weeks of working for Skillcrush, the extra hours of paid work didn't have much of an impact on my unpaid work of housework and childcare duties—until one particularly dark, rainy day when the dishes had piled up, a chimney leak was letting water into the living room, my kids had an early release day from school. . .and I had an article due that I hadn't even started yet.

At the time, I'd banged out my first few Skillcrush articles without really knowing what I was doing. I started at Skillcrush in the middle of the holiday season and bounced between different roles before settling into my current place on our editorial team, so I didn't have an official, black and white training period. This—combined with my overall lack of experience—turned each article I wrote into an anxiety-laden experience. Whenever I finished writing I felt like, "Oh thank god! I finished it, it's over! I don't have to do that again!" But—of course—this was a job, and after one article was finished, the next one needed to be done. And this particular rainy day was the first time my mounting anxiety partnered with my backed-up domestic duties to make the whole thing feel impossible.

I remember totally freaking out: "WTF have I gotten myself into? There's no way I can get everything done!" But after a few deep breaths I started the article, took a break to pick up my kids, finished the article, and excavated the dishes. The leak got fixed about 6 months later, but the point is: There was time to do it all—I just had to focus on one task at a time, and everything started to fall into place.

In the months since—whenever my schedule starts to seem overwhelming—I think back to the methodical approach that pulled that day together, and it makes me remember that the focus of having part-time remote work on top of my domestic duties actually makes me more efficient all around. There's a greater feeling of urgency to get everything done, which means there's less time spent procrastinating and avoiding—I literally can't get away with putting things off anymore—and that's been a positive change in my life.

What's the Plan?

That said, I have had to be proactive in my new, efficient life back in the workforce. Paid work is a whole new world—particularly if you've been out of the game for awhile. You have to learn the ins and outs of how your workplace functions, navigate a new set of social interactions, calibrate your ability to meet deadlines, and (if you're working remotely) remember to change out of your pajamas in the morning. It took me a few months to get used to all of this, much less to get to a place where meetings and reporting to managers didn't automatically fill me with dread—not based on anything anyone else was doing, but just due to my own feelings of inexperience and insecurity. The ability to figure all of this out and still get work done doesn't come together accidentally or automatically. It's all on you to establish systems and habits that will help you succeed. I learned this the hard way.

For my first couple of months I had a completely scattershot approach to working—no plan for when I was going to work, no breaks built-into my schedule (because I didn't have a schedule), entire days spent forgetting to drink water or eat anything—and I was starting to feel completely rudderless and out of control.

I'd start my day intending to do paid work, but then I'd notice some things that needed to be done around the house and I'd decide to take care of those first. Of course—en route to doing vacuuming or laundry folding—I'd put off making coffee or eating breakfast, but after a few hours of chores I'd realize the day was slipping away, so I'd absent-mindedly sit down at the computer, "just to get started." Four to six hours later, my paid work was done, but I was totally fried and wrecked going into the next day where I'd begin this haphazard run all over again.

This approach obviously wasn't working, so at a certain point I had to take a time out and reassess—I'd read all the articles and seen the advice about how you need to create structure when working from home (schedules, breaks, an environment conducive to getting work done, etc), but I'd kept telling myself I'd get to it eventually. The truth is it's all stuff you need to address on day one (or if you're past day one, then right now).

In the months since, I've adjusted my approach—the night before a work day I make sure the house (or at least the area I'm going to be working in) is clean enough so that I'm not distracted, I put off all non-essential housework during the day until I'm done with paid work that's due (or that I've scheduled to get done that day), I keep a written log of what I'm working on in Google Docs, I add due dates to my calendar, I mindfully schedule when I'm going to do what, and I try to stick to the same routine every day as best I can. The results of this approach have been night and day—I now feel like I have a handle on what I'm doing, and I'm able to maintain physical and mental health while also working and caring for my house and family.

In my year at Skillcrush, I've had my eyes opened to how many opportunities there are—not just for work in tech—but for quickly gaining the skills needed to start new careers. I always thought that starting a new career would require years of school and certifications, and that's just not the case. In interviews I've done with tech professionals and conversations I've had with Skillcrush alumni, I've been surprised at the number of people who were in similar situations to mine, and how many success stories there are when it comes to remote work, online coding classes, and other non-traditional venues as a path for returning to the workforce.

I worried about the adjustment, too, but that also fell into place (with some proactive but manageable work on my end), so if you're looking to add paid remote work to your domestic work as a parent or an at-home partner, don't let the extra hours and duties intimidate you. You'll likely find that the tension between paid work and other responsibilities will actually make your days more focused and efficient.

And maybe the biggest bonus is one that was totally unexpected: At a time in my life when I was set in my ways and thought I'd met just about everyone I was ever going to know, I've been introduced to a whole new cast of smart, funny, creative, inspiring people, all while learning new things every day and getting paid. I'm not sure how it gets better than that, and now that it's so integrated into my life, it's weird to think that this part of me didn't exist just a year ago.