In my 25 years of work history, I've often joked that I've held every job that a 10-year-old boy would dream of having, short of firefighter and professional athlete.
I worked for Playboy, ran a giant toy store, served as director for a group of rock-band summer camps, and scored a staff position at the newspaper I read while growing up, The Boston Globe. Each position was a dream job in its own right, and I didn't get any of the jobs by accident or simply by sending a resume and hoping for the best.
To get your dream job, you need to work every angle and put yourself in position to succeed. Even that won't guarantee success, but it will at least put you in position to succeed.
People like to hire someone they know, and many enjoy being the hero in recommending someone. That means that if you identify ways to professionally meet people in the organization or profession you want to work in, you will be well on your way.
This could be as simple as attending industry events and making connections, or it could be requesting informational interviews with people who may someday hire you. It's a good idea to ask questions like "what skills or experiences would make me stand out as an applicant?" It's also important to listen, send a brief thank-you follow-up, and, if possible, connect with relevant people on LinkedIn.
2. Gain needed skills
Many years ago, before I had worked as a business journalist, I applied to be the editor of the local business journal more than once without getting an interview. I was an experienced editor, and when I was lucky enough to meet the person hiring for that job at a local journalism event, she told me she knew who I was, but felt I lacked specific business-journalism experience.
Taking that advice to heart, over the next few years I pursued roles that gave more that experience. I had bylines in business sections, I ran the business desk at Boston.com, and when the top job at the local business journal came open again, I interviewed multiple times, though we ended up not making a deal.
If you want a specific job, find out what the people who fill that position are looking for, and then go and get those skills. Even if you don't end up in the job you thought you wanted, you may find other desirable doors popping open for you.
3. Be willing to start at the bottom
Sometimes ego can get in the way of getting where you want to go. Perhaps you're important and successful in a career you don't like. To transition to another field -- one you may actually be happy in -- you may have to bet on yourself and start at a lower level.
If you get your foot in the door, it's possible to show your worth to the organization. It's not about where you start, but where you end up, and if you're humble enough to take a step or two backwards, eventually your other skills and experience will become evident.
4. Have a plan
A number of times that I've been hired for dream jobs, I started as what I consider a novelty candidate. My resume was not dead on, but my experience and cover letter got me the last interview slot, where I would have to overcome in-house candidates or people already in the field.
The only way to overcome those deficits is to blow away the interviewer. That means prepare like an NFL coordinator getting an interview for a head-coaching job. Have a presentation ready for both your immediate and long-term goals for the position. Don't be arrogant and pretend to have all the answers, but lay out your first 100 days and what you will do to leverage your background with the experience of your potential new coworkers, bosses, and direct reports.
5. Be open to anything
In most cases, dream jobs gain that status because so many people want them, and most won't get them. That means no matter what your end goal, it's important to remember that for nearly all of us, there will be detours along the way. Sometimes those detours lead to new destinations and open up paths to dreams other than the ones we first pursued.
None of my dream jobs turned out to be actual dreams. They all had their moments, but most importantly they helped me gain the skills to lead to my current situation, a dream job I never knew I wanted, that became possible only through the pursuit of different dreams.
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