Updated: Mar 18
The art of getting from where you are to where you want to be.
It has happened to the best of us. Overpaying for education and crossing our fingers that that education will lead us to our dream job. At times we’ve even doubled down on that approach and paid for even more education aimlessly. Oftentimes the degree obtained is not worth the paper that it’s printed on. Okay, that's dramatic, but you get my point.
We’ve also taken a job because we needed the money or because we thought that’s what we wanted to do. If you are part of the fortunate yet misguided, you’re pursuing a career you thought you wanted because your family steered, or maybe pushed you begrudgingly, in that direction.
If you aren't in the right career, and you’re lucky, you’ll realize sooner that sooner than later. Regardless of when you have this realization, you still have a plenty of time to make a change. I don't care if you are 18 or 65. There is time. I’ve been there myself, I have friends and family that have experienced this, and now I find myself working with clients who have come to a similar crossroads.
Suppose you’re a fresh-faced 18-year-old entering the working world and coming across this; lucky you, truly. I wish I had known the following information when I was your age. I would have avoided a lot of missteps in my career and found my dream job sooner. But maybe then I wouldn’t be blessing you and the rest of the world with this hard-earned wisdom. You win some, and you lose some 🤷♂️.
Step 1: How do you get jobs?
"You get jobs by talking to people."
- Don Asher
I often ask my clients, “how do most people get jobs?” They all inevitably answer something to the effect of "you get jobs through friends, your network of people you know, etc.." Basically, nepotism. (You don't have to like it, but understand that is how the game is played.) My next question is, “how are you going about your job search?” They inevitably respond with “looking at job boards and applying for the opening I come across that fit my skill set and/or experience.” We understand that most people get jobs through their network, yet, when it's our turn to look for a new job, we rely on the good ole job boards. Make it make sense! I don’t fault anyone for the disconnect here. I used to be in the same position. I know better now, and I want to assist you in avoiding the same mistakes that I made and help you get to where you want to be most expeditiously.
Step 2: Identify your Dream Job
"Dreams are extremely important. You can't do it unless you imagine it."
- George Lucas
Let’s start with what I mean by a dream job. The job you’ve always thought you wanted, but your journey took a detour for whatever reason. Now, we are course-correcting.
Many of us know what we want to do but think, “we can’t do that,” “it’s not practical,” or “my spouse, family, or friends will think I’m silly,” we hold ourselves back. We put imaginary limitations on what we can accomplish. The lie we tell ourselves is that others who have experienced achievement in an area where we want to experience achievement have a superior intellect, skill set, or more money or resources than us to get started. They don’t. I mean, some do, but not all. (The world is not fair. Get over it.) We made up those stories, or excuses, to comfort ourselves from having to do the hard things and start working toward our goals, in this case, our dream job.
Don't @ me. I understand life is challenging, and there are obstacles. Some of those are within our control, and others are completely outside of our influence. Focus on what is within your control, and let go of what you can't control.
Step 3: Pen to Paper
“The hand that holds the pen writes history.”
- Film “Colette”
I’m a big believer in the power of putting pen to paper. Writing things down has helped me and many others gain clarity on any matter with which we were struggling. Take out a pen and a notepad and start writing. Pen, not a pencil. We aren't in elementary school! Below there are some prompts that I would recommend that you start with, but don’t limit yourself to just this list. Let the pen do that work and start writing.
1. If money were no object, and you could live anywhere and do anything, where would you live, and what would you do? The key to answering this question is to not think about it particularly. Be selfish, and don’t worry about how much you’d be getting paid, location, family, etc… Remain laser-focused on what YOU want to do. We will spend time figuring out the details later. The standard pushback I get here is, “Randall, that’s nice, but I have responsibilities.” We all do. There will never be a perfect time or perfect situation, you have to get started doing the thing now and figure out the details as you move along. Now is not the time to limit yourself.
2. Do I enjoy my current job? Which jobs have I enjoyed the most? Why?
3. What are the responsibilities of my current job that I enjoy and those I don't?
4. What’s your number? What is the minimum amount of money you must make to cover your necessities? Food, water, shelter, and bills you are obligated to pay, i.e. insurance, mortgage, student loans, car note, etc...
Avoid matching your present skillset to jobs that would suit your skillset. We are NOT trying to match our present skillset to jobs we would be proficient at. We are trying to identify our dream job. That could mean acquiring a new skill set, relying on dormant skills, or turning a hobby into a business (sorry to sound like an inspirational Instagram post).
There is behavioral economics theory, the sunk-cost fallacy. It’s a situation in which you find yourself reluctant to pivot, course-correct, or change lanes because you have made a significant investment in your present strategy. Oh, I dunno. A significant investment of, say, spending way too many years in a career you don't enjoy.
If you’ve gone to school to be a nurse, and you’ve been a practicing nurse for 10 years, I would assume that you have a skill set that makes you a proficient nurse. Moreover, you’ve also made a significant investment to be a nurse with the time, energy, effort, and money you invested in nursing school and the decade you’ve already spent in the field. Two things can both be true in this instance, 1. You’re a great nurse, and 2. You despise it. Should you keep doing it because you’ve invested so heavily and are good at it? Of course not! Personally, I’m great at aimlessly digging holes in the ground, but do I ideally want to do that every day? No! End rant, moving on.
Step 4: The Search
"He who would search for pearls must dive below."
I'll hit you with a little preview because The Search deserves an entire devoted post.
Through the above exercise, you should be 75% of the way to understanding what your dream job is. You're only 75% of the way there because you've never had this job before, you've never searched for this job before, you've never gone down this path before - we still have some figuring out to do.
Major key alert: be deliberate and intentional with your search activities. We no longer cast a wide net. We are spearfishing (to add to the analogy).
1. Share with your TRUSTED friends, family, and professional network that you are now pursuing a career in [insert dream job].
2. Connect, LinkedIn or otherwise, with people that you know are presently doing your dream job and see if they will make time to discuss their journey of how they got there. This is more likely to happen than you might think. People love talking about themselves.
3. Connect, LinkedIn or otherwise, with recruiters and hiring managers that are hiring for your dream job. Not only connect but proactively reach out to them, regardless of whether or not there is a present job opening. If you can find their phone number, call them. If not, send them a LinkedIn message or an email. When you write them, make the message unique and compelling enough to stand out.
4. Yes, job boards, there I said it. I hope you are happy! Job boards can be valuable, but not necessarily in the way that you think. Search for your dream job, assuming it's not an entrepreneurial endeavor, and apply for those openings. Then, find out who the recruiter and hiring manager are and call and/or email them to express your interest in the role. When most jobs are posted, the organization knows who they want to hire. Again, nepotism.
However, you might get lucky, and that might not be the case.
The primary value in this exercise is 1. learning more about the dream career path you've decided on, 2. getting better at interviewing, understanding what the typical interview is like, 3. understanding where you are at verse the competition, 4. TALKING TO PEOPLE. This puts you in a position to talk to more people. Perhaps you won't be their candidate this time, but next time there is an opening, and you've done your job of staying top of mind of the hiring manager, perhaps you'll be the person they have in mind for the job before the posting goes up. You're welcome!
5. Track your activity and contacts, almost like your own job-searching CRM. This will allow you to periodically reach out to the people you've built relationships with so you stay fresh on their minds. Pro-tip: We aren't asking for jobs when we do this. We are doing stuff like, "I saw this article and thought you might find it relevant."
Step 5: Quick Hitters
Make sure your house is in order
Make sure your resume can compete with the competition. But I’ll drop a few nuggets of wisdom below.
Google image search “modern resume,” your resume should look like one of those
Your resume is not a job description of the past positions that you’ve held. It is a professional brag sheet. Write it accordingly. Say “I” often, use assertive language, “I spearheaded/Led/etc…” When you can take full credit for a project, do so.
Don’t limit yourself to just one page.
Anything position over 10 years can be dropped unless it is extremely relevant to the jobs you are pursuing.
I believe education is less important than experience. Put work experience first, education afterward.
Quantify items where you can, “I increased this thing by X%," "I led this initiative and increased revenue by x%."
Ensure your LinkedIn profile is up to date and fully optimized, and you have a profile picture.
Step 6: The Journey Continues
"Sometimes, it's the journey that teaches you a lot about your destination."
Oftentimes, when I take my clients through this exercise, they realize that their dream job would be what they always wanted to do but were sidetracked from pursuing it. Think Pastry Chef because it doesn't pay well, or I'll smell like sugar all the time. Or they know they have always had an entrepreneurial mindset but have been surprising the urge and/or afraid to leap. Smell like sugar, start a business, fail, learn, succeed, repeat.
If you've been intrigued by this post and think that you could benefit from some additional guidance. Please reach out to me at firstname.lastname@example.org
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