Quick question: If money wasn't an object, what would you do for a career?
What was your gut reaction, initial, no-overthinking response? Is it worlds apart from what you do now? Or is it being the "bomb ass boss" at your current gig?
What is it you want to do with your career, really?
I know, I know. Easier asked than answered.
Or just maybe, deep down you know the answer, but you're afraid of the answer or you have no idea how to move forward.
You might be sitting at your desk, asking "Is this it?" "Is this the best career for me?" "Because I'm not super happy and sort of want to strangle my cubicle-mate." Even if your cubicle mate is your actual mate because, work from home.
First off, slowly back away from your desk and realize that you're going to need to get real with yourself if you want a meaningful career, including a job that will make you happy.
Where Happiness at Work Actually Comes From
Job satisfaction is comprised of a lot of factors, but for you to be truly happy at work, you need to focus on yourself. Your personal connection to the work is where the happiness comes from.
Here's what I learned through two major career changes of my own: I used to be a professor. Yup. I taught courses like "The History of Creativity." That's totally a thing. Did you know that was a thing? I LOVED being a professor. But I also loved paying the rent. I'm not sure if you know this, but academia isn't exactly a cash cow.
I finally hit a breaking point financially and was forced to reconsider and reevaluate.
I tried out a few things, but nothing felt right.
I knew I wanted to continue educating and helping people find their thing. I knew I liked helping students figure their own stuff out. It was when I finally worked with a career coach that it became clear.
I specifically wanted to help people with their own career development and growth. It makes sense, right? Teaching college is helping students figure out what careers and futures they're interested in. Career development is the next logical step. Career development just made all sorts of sense.
Cool, but knowing what I wanted to be was only part of it. I had to figure out how to make my teaching skills make sense in corporate-land.
I made my way back to advertising and marketing, where I had worked until grad school. I dabbled in several roles until I found my footing in creative staffing. It's truly a mix of recruiting, management, learning and development, and a healthy dose of career coaching.
In my years of staffing candidates and coaching clients, as well as finding my own sweet spot, I've learned that finding a fulfilling career requires getting honest with yourself. Really honest.
The Power of Asking "Why?" Five Times
In order to find a job that makes you happy, you need to ask yourself ONE tough question, five times. Seriously.
This technique, borrowed from root cause analysis, helps you dig past surface-level complaints to understand what you actually need.
Step 1: If you are not currently happy at your job, ask WHY.
This is where you get to leave the stuff you don't like behind you. It goes like this:
"I don't like my job because I hate my boss." WHY do I hate my boss? "She's demanding." WHY is she demanding? "She acts like I don't know how to do my job." WHY does she act like that? "She is stressed all the time." WHY? "There are only two of us to do all the work." WHY? "It's a small company."
Based on all that, you may need to find yourself a larger company that allows you some trust and autonomy to do your job. Once you do this for the multitude of reasons you're currently unhappy, a picture should start to emerge of the type of job, company, and environment that will allow you a bit more job satisfaction.
Step 2: Ask WHY you want to work (other than a paycheck)
We all need to pay the landlord, but other than that, WHY do you want to work?
For example: "I want to have a sense of purpose." WHY? "I want to feel fulfilled at work." WHY? "I need to know that what I do matters." WHY? "Because otherwise, I'm just wasting my life." WHY? "Unless you're doing good, there's no point to it." WHY? "Doing good is the whole purpose of life."
You might need to find yourself a job or company that gives back in a big way. This may mean a gig in a small nonprofit, a massive corporation with a charitable foundation you can work for, or a midsize company with lots of volunteer days.
Step 3: What abilities, interests, and skills make you feel good, strong, and engaged?
Keep in mind that just because you're good at something, you don't have to do it for a living. I mean, I'm great at laundry, but I'm not about to open a dry cleaners.
So, what interests and skills do you have?
"I'm interested in art." WHY? "It's amazing to see all the ways someone can express themselves." WHY? "It really shows just how unique we all are."
Anything else?
"I'm good at organization." WHY? "I just get how to keep things straight so they're easily accessed." WHY? "My brain just sees things in a logical, mathematical way."
Who knows, maybe an operations position in an art gallery would knock your socks off. Maybe a solo business where you organize closets and show people how to dress creatively with items they already own could be your jam.
Step 4: How do you work best?
Under what conditions do you work best? Do you have a boss and are part of a team, or are you a solo-preneur? Do you go to an office, work from home, or the beach? How many hours do you put in and how much money are you making? Basically, how do you want to live life? WHY?
"I prefer to work in an air-conditioned office downtown." WHY? "I like the structure of having somewhere to go." WHY? "Otherwise I'd never put on pants." WHY? "I really like being at home, on my couch, with my dog and being comfortable, so going to an office makes me act like a real human." WHY? "Because I'd happily work in my underwear with Judge Judy on for background noise while eating PB&J every day if I didn't have to get dressed." WHY? "Because that's what makes me happy!"
Just saying, maybe you really do want a gig that lets you telecommute. Just put on a decent shirt for those Zooms, okay?
Step 5: So what?
This is where it all comes together. Go back through your answers to steps one through four and pull out what feels the MOST important to you. Now hit those with WHY.
I want to work part-time: WHY? So you can surf in the mornings? Awesome, brah. I prefer to work on my own: WHY? So you can be in charge? Get it, girl. I love the social media aspects of my job: WHY? It's engaging and fun. You betcha. I want to help women and folks with my work: WHY? The gender wage gap needs to go. Amen.
How does a remote social media strategist for small businesses sound? Boom. Done. Now go find yourself some true career happiness.
The Four Steps to Making It Happen
It really is about digging deep and being honest with yourself. I know you can do it. But once you know what you want, you need a plan to get there.
1. Start with Yourself
Outside of societal and family pressures, you need to acknowledge who you are and what you truly want. What your values, likes, and priorities are.
This doesn't have to be daunting. It can be as simple as sitting down with a pen and a notebook and really asking yourself what you want from life and how that reflects what's important to you.
Use the five-why technique above. Journal. Make lists. Talk to yourself out loud if that helps. The point is to get brutally honest about what you actually need to be happy, not what you think you should need.
2. Reach Out
Now that you've had a nice conversation with yourself, it's time to chat with other people. Especially people in your network.
Your network is a goldmine.
Want to know what it would be really like to be a preschool teacher or graphic artist? Reach out and ask. Someone you know is connected to everyone you want to talk to.
Use LinkedIn, email, your alumni association, your hair stylist's sister. Reach out and ask to take them for coffee or set up more formal informational meetings.
Everyone's favorite topic is themselves, so don't be afraid to politely ask. Most people are genuinely happy to help someone who's thoughtfully exploring career options.
3. Do the Work
Shadow, volunteer, and do freelance projects if at all possible. Even a few hours a month can give you real insight into a new role and lead to a vast network of connections.
If you're already working three jobs and just can't make the time commitment work, try squeezing in an e-course, webinar, or nighttime reading that is relevant to your career goal.
The point is to test your hypotheses. You think you'd love being a graphic designer? Great. Do a project or two. You might discover you love it, or you might realize you actually prefer the strategy side of creative work. Both discoveries are valuable.
4. Sell Yourself
Now that you know who you are, who you want to be, and what work you want to do, it's time to sell yourself.
You really only need three things to effectively market yourself into the job you want:
LinkedIn profile (recruiters live and die by it)
Portfolio/Website (no matter what your line is)
Resume (yes, still)
Whether you are a career changer, freelance maven, corporate rockstar, or newbie grad, you need sales collateral. Yup, it's true. That's exactly what these things are, and if used correctly, they can do most of the job hunt work you hate doing.
If you've got all three of these buttoned up, recruiters will call you. For the rest of you, you need to get set up to sell yourself ASAP.
Building Your Sales Packet
Where do you start? With your story.
Before you slap together a profile, format a Google doc, or whip up a website, you need to start with a clear story of who you are, where you want to be, and why you want to be there. Most people treat their resumes as a list of past job descriptions. What you should be doing is using them to tell your story. To outline why you're the perfect fit for that bigger, better job.
Gather a list of five to 10 bullet points that highlight your unique value, impressive stats, and skills you want to build on. Use these "Story Bullets" to build out your summary, job history, and "about me" pages. Your LinkedIn, resume, and website need to be cohesive and work together. Using the same wording for your summaries on each will not only save you time but help you form your personal sales pitch.
Look at your bullets and focus on the ones that a recruiter hiring for the "next big gig" you want would be searching for. Don't focus on the job you want out of. Show that you're right for the next level up.
For example, Jack, of Beanstalk fame, might have the following bullets:
Co-Founder of Giant Slayers Inc, which sold for 45 million farthings
Deep understanding of the gold-egg market
62 percent rise in used-cow sales within two years
First to market with singing harp services app
These could be summarized as: "I'm a marketer with six years of in-depth experience in multiple markets including golden eggs, harps, and cows. My experience in multi-channel campaigns, campaign management, and technology development has given me unique insight into the giant-slaying arena."
Now, for his job history sections, Jack should list his absolute best or biggest accomplishment, or story bullet, as his first. Again, highlight the skills and accomplishments that will appeal to the hiring manager you're gunning for. Don't just rewrite your current job description.
A portfolio for creatives is a 100 percent must, but it can be invaluable to all types of professions.
What's the first rule of story writing? Show, don't tell. Well, a website lets you show, not tell, your skills. For many people, building a website feels intimidating, but it can be a simple templated site hosted on a free or low-cost service.
Your Bare Basics Checklist
LinkedIn:
Photo
Summary
Contact info
Job history with key bullets featured
Skills listed
Portfolio/Website:
Photo
Summary
Contact info
Links to social accounts
Links to relevant content: blogs, creative works, case studies
Link to resume
Resume:
Summary
Contact info
Job history focusing on key bullets but with more complete skills and accomplishments listed
Skills section highlighting those most useful for the job you are going after
Making It Strategic
Three emails sent to viable network connections are worth 50 resumes sent out into the internet void.
Do your research and tailor each application, cover letter, and email to that specific person, for that specific role, that you are specifically interested in and fit for.
This whole process can take days, weeks, or even months. Go at your speed and try not to play the comparison game. Who cares if your younger cousin appears more successful than you. You don't know her life.
Eyes on your own paper, butt in your own lane.
Focus on you and your path.
The Bottom Line
Finding a job that makes you happy isn't about chasing some vague passion or settling for misery because you think you're stuck. It's about getting honest with yourself through deep questioning, understanding what you actually need to thrive, and then strategically positioning yourself for the work that aligns with those needs.
Start with the five whys. Figure out what you actually want, not what you think you should want. Then reach out, do the work, and sell yourself effectively.
You don't need to start from scratch. You just need to understand yourself better and communicate your value more clearly.
Now go get 'em, tiger.
Yours in you really can find work that makes you happy goodness,
EBS
