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The 7 Top Challenges for Millennial Job Hunters

How boomer and Gen X parents can help their kids overcome them

By Valerie Dorn

(The following is excerpted from the new book, Millennials in Wonderland: Coaching Grads at the Crossroads of Life and Career by Wendy and Kenneth Schuman. The website for the book is Millennialsinwonderland.com.)

Millennial
Credit: Adobe Stock

If you are the parent of a Millennial, you probably know how difficult it can be for recent college graduates to navigate the potentially stormy waters between graduation and establishing themselves in an initial career path.  Millennials are simultaneously excited and overwhelmed by the possibilities before them but can become discouraged when they don’t land their dream job immediately upon graduating from college or grad school.

Below are the seven biggest challenges they face looking for jobs and how to empower your Millennial kids to create their own unique path forward toward their dreams and goals:

Challenge No. 1:  Holding on to beliefs that no longer serve them. As a professional coach, I worked with a client in her 20s who had studied engineering in college and started a career in engineering. After a few years, she was laid off and had been unemployed for almost a year when we started working together. She did not have any energy or enthusiasm for her job search, which, as it turned out, was because she no longer wanted to be an engineer.

After giving herself permission to think beyond what she had gone to school for, she discovered that she actually had a passion for teaching girls math and science. After volunteering at a public school for a couple of months, she realized that teaching was a perfect fit for her. All she needed to pursue this new path was to obtain teaching certification, and there were several accelerated programs that would enable her to begin her new teaching career in only a year.

Often, twentysomethings think it is too late for them to change direction or believe that if they do something different, then everything that they have done up until now has been a waste. Help them to see that their past experience and education is not only valuable but also a necessary step along the way to where they are going. Explain that their first (or second or third) job will not be their last and only job; it is OK to use the next job as a stepping stone to bring them closer to their ideal job.

Challenge No. 2:  Not recognizing their own strengths and values. In working with Millennials, I have found that many of them do not recognize or know how to articulate what their skills are and how that translates into a job.

For example, I worked with a recent college graduate, Sherry, who did not think she was qualified for the jobs she wanted to apply for. Together, we broke down the job descriptions into concrete skills and compared them to her experiences on her resumé.

Sherry had extensive experience working in retail, which she thought was menial and irrelevant. However, upon closer examination, she realized that she had supervised and trained new associates, which demonstrated leadership skills that she thought she was lacking. We went through her resumé one experience at a time, including work, volunteering and extracurricular activities. By the end of our conversation, Sherry was not only clear about what she had to offer an employer but was also feeling confident in applying for the positions she wanted, understanding her value for the first time.

A critical aspect to a successful job search is having a clear understanding of one's values and how they connect to finding meaningful work. You can help your Millennial identify and prioritize his or her values. There are many free values assessment tools online. Assessing values can be especially helpful for people who do not enjoy the work they are currently doing or are not sure what kind of work or work environment they would enjoy.

Once someone knows what he or she values most, it is often much easier to narrow down career options across different variables, such as geography, industry and work environment.

Some guiding questions: What do you value? How are your values being honored or not honored at work? What are your strengths? How closely aligned is your current job with your strengths?

Challenge No. 3:  Not knowing what they want. Our educational system provides a clear, step-by-step roadmap through college or graduate school, but after that, graduates often feel lost —  especially if they are not following a more traditionally defined professional career path such as medicine or law.

In working with Millennials, I have found that they are looking for someone to tell them what to do. They want “the answer” — a clearly defined path from where they are now to where they think they want to go.

For example, I had a client named Leslie who desperately wanted someone to tell her what the correct next step was. She found herself receiving both solicited and unsolicited advice from everyone, and whenever that advice conflicted with her desires, she found herself feeling defensive and resentful. Through our work together, Leslie decided to stop asking for advice. We came up with strategies for how to respond effectively to unsolicited advice in a way that was respectful to both parties. As Leslie let go of what others were telling her she should do and started to listen to what she wanted from her heart, her confidence in her own judgment increased.

Another situation graduates often find themselves in is being dissatisfied or unhappy in their current job but not knowing what would be better. For example, I worked with Ken, a designer at a graphic design firm, who enjoyed his work, but did not like the environment he worked in, which was competitive and critical. He thought he might want to give up graphic design completely, but with further exploration discovered that maybe it was working specifically in the highly competitive graphic design industry that was contributing to his unhappiness.

Ken realized that other industries also needed graphic designers and started applying for in-house design positions. He quickly landed a position in educational publishing, where he was one of only a few graphic designers in the organization. As a result, his work was deeply appreciated by his non-graphic designer colleagues and he was no longer competing with co-workers to land good projects.

Try to help your Millennial home in on the exact elements of his or her work or work environment that are not a good fit, so your child can be clear about what he or she is looking for in a new job.

Guiding questions: What do you like most about your current position? What do you like least about your current position? What would an ideal day look like? What skills do you want to gain/develop in your next position? What kind of an impact do you want to have through the work that you do?

Challenge No. 4: Having no clear strategy. This pitfall results from a combination of Challenges No. 2 and 3. As a coach, I have seen many graduates applying for jobs using the strategy I call “applying for anything and everything that I think I am qualified for.”

It is easy to fall into this trap if you lack self-awareness around your strengths and values and don’t know what you want. By not being discerning in their search, graduates find themselves feeling overwhelmed, exhausted, frustrated and fed up with their job hunt. In addition, they may not be considering positions that are a bit of a stretch or may be somewhat outside their field but might be good stepping stones to build skills to get to their dream job.

For example, I worked with, Lara, a client in her 20s, who after graduation continued to work as a barista at a coffee shop while applying for any and every position in the country she thought she might be interested in and qualified for. By the time we started working together, Lara was discouraged by the lack of results and was starting to believe there was something wrong with her. In reality, the problem was having no clear strategy.

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Through our work together, Lara was able to limit her geography to a few specific areas of the country and focus on applying for a few different types of positions within one industry: travel. By being more focused, Millennials actually feel more free and successful in their search.

Challenge No. 5: Feeling isolated. Looking for a job, especially while living at home, can be very isolating. Graduates go from being surrounded by the support of their peers to being in environments where they may be the only person their age, and thus often feel like no one understands what they are going through. In addition, graduates are used to receiving a lot of external reinforcement in college, and without that, they can feel discouraged and unmotivated.

It can be helpful for graduates to seek the support of someone their age who is going through the same process they are, which can be incredibly validating and motivating.

Graduates often compare themselves to their peers, especially through social media, and believe that everyone else has everything figured out — that they have all found jobs they love, are making good salaries and are living well.

Help your child figure out if the time he or she is spending on social media is supportive or destructive to his or her confidence and self-esteem. Help your Millennial find outlets where your child can connect with peers in similar situations.

Sometimes the safety net of family support can become a crutch. It’s helpful for graduates living at home to identify and weigh the benefits and drawbacks of living at home to help increase their motivation and confidence in finding a job that enables them to move out, if that is their ultimate goal.

Challenge No. 6: "All or nothing" thinking. Young adults tend to think in terms of black and white: all or nothing. For example, a client I was working with, Carolyn, told me about how she used her network to land an in-person interview for an ideal position in an organization whose mission was aligned with her goals and vision. In the end, she was not offered the position and she jumped to the conclusion that “networking does not work.”

I encouraged her to re-examine the situation step-by-step from a different perspective. As we did that together, she realized that although the end result was not what she wanted (the offer of a job), that didn’t necessarily mean that everything she did along the way was worthless.

Affirm your child’s courage in taking steps toward his or her goal and reinforce the actions that are producing necessary steps on the path to landing a meaningful job. By reinforcing appropriate and effective job search activities, you can help build confidence that the steps your child is taking are the “right” steps, even if they do not produce an interview or a job offer every time.

Challenge No. 7:  Overreliance on technology and lack of attention to detail. Millennials are extremely comfortable using technology, and while it can be an incredible tool to use in their job search, it should not be the only tool they are using.

I have worked with many clients who had been sending out hundreds of resumés with little to no results. One of them, Cate, had been diligently sending out 10 to 20 online applications every week and the only responses she was receiving were “no” if she heard anything at all. Cate did not have much experience networking in person and was not sure how to network or where to begin.

You can help your Millennial figure out what his or her network looks like; your child may be surprised at how big it actually is. When Millennials see the value in networking and have confidence in their ability to network, they will not only feel more empowered in their job search but also start to see some concrete results.

Another challenge I see some Millennials face is a lack of attention to detail in their cover letter and resumé. While much of their digital lives does not require perfect spelling or grammar, proofreading cover letters and resumés is absolutely critical for a successful job search. Make sure your child has clean, clear, error-free resumés and cover letters.

In addition, make sure your son or daughter has sanitized his or her social media profiles. Many employers screen applicants by doing an online search for them, and if they come across anything questionable, they will eliminate those applicants from the process.

As young adults, Millennials are still figuring out who they are, what they value and what success means to them. You have an incredible opportunity to support and guide yours to help create a successful, repeatable process for finding the next job opportunity that is the right fit.

Valerie Dorn is a certified professional coach and owner of Find Fulfillment Coaching. She volunteers as a coach with Grad Life Choices to assist low-income grads and is also a yoga and meditation teacher. Visit her website at Valerie-Dorn.com. Read More
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