In Pursuit of Fulfillment: How to Define Your Dream Job

What do you really want from a job? A nice boss, flexible hours, interesting work? Maybe you’d, jokingly but secretly, try to get away with not even having a job if you could. Maybe you stopped asking yourself what you want, after you stopped asking yourself what you wanted to be when you grow up. And you just went with it: life, expectations, status, money, whatever.

Last weekend, after I had finished writing 95% of this series on dream jobs and the modern job hunt, I found myself eavesdropping on a conversation two women around my age were having next to me at a coffee shop. I didn’t mean to; they were just talking about careers, jobs, fulfillment, so of course. There were a lot of “I don’t know”s and “I just want”s, a blend of hopeful optimism and hopeless anxiety - I couldn’t tell which, probably both. I made a note to self in my Leuchtturm, pretending that I was making my own plans when in fact I was spying on strangers. I scribbled to remember this, underlining: why does everyone want to “just travel”?

I’ve asked this before, to people in my own life, what they’d love to be doing instead of the jobs they hate so much, curious what a day-in-and-day-out life hating most hours of your day feels like and what they’d prefer instead. The answer is just a summary of this coffee shop conversation: “I don’t know… I just want…to travel.”

And so here I am. The openness and unknowns, the one big glorious self-care moment wrapped up in the exploration of culture, of risk-taking actualized and not simply an act of indulgence, all of this makes the idea of travel an easy culprit for a life well-lived. It’s not that I don’t think travel shouldn’t be a goal, but more that the biggest lie we tell ourselves is that we’d be happy if only we all didn’t have to work. Actual happiness, or the better and more constant feeling of fulfillment, is much more complex. And probably most of us would be more fulfilled doing fulfilling work rather than no work at all. And really, you could replace travel with whatever the scapegoat aspiration of your generation or industry is.

It’s a big, lumpy topic.

Meg’s final column in our Ask a Designer series explored the complex and exhilarating time in a young creative’s journey embarking on their first job hunt in an uncertain world, layered on top of an uncertain self. A few weeks ago, we surveyed the SuperHi community to help us dissect dream jobs and the entire job hunt process. We wanted to know what your challenges are and what your job hunts have really been like. You echoed the same anxiety as our soon-to-be-graduate letter writer and told us things like this:

With how many people are disengaged in their jobs (studies cite as high as 85% of us - that’s a vast majority, not the rare disgruntled), disengaged workers are the endemic of modern work. We’re burnt out by the very idea of work and the whole process around finding it. It’s kind of comforting to know that it’s not just you and that it’s a challenge for most of us, but also disappointingly alarming.

Where we’re at right now is a wake-up call, an in-between space we’re all trying to figure out, one of unprecedented technological change and broken down systems asking for more. And I think within that beautiful mess, there’s room for all of us to craft our careers and job hunts with intent. We have to try. Otherwise, we’re just all living in a world where discontent is the norm, and that’s no fun at all.

You may be like many, seeking a specific company, role, title or salary as the pinnacle of a great career. The big disconnect, why most of us are so unhappy and planning our escapes, just might be because we’re searching for the wrong things. But, what does it take to really be happy at work? In the first article of this series, we tackle that by dissecting all the elements of a job so that you have a baseline knowledge of what’s out there and what’s possible. Let’s go!

The elements of a dream job

🏢 How big is the company?

Many creatives lean towards smaller companies perhaps because smaller companies are thought of as doing more niche, interesting work. It can be more common but it’s not necessarily true: there are small teams and divisions at much larger companies working on all kinds of interesting projects within the context of a larger organizational vision. Big companies are great places to get what you need, whether you want to meet lots of people or stay under the radar; there’s room for all kinds of preferences. And, it’s often the giants that have enough resources to create divisions just for departments like creative R&D, whereas in smaller businesses, you might be more likely to take on many roles.

Company size is also a good indication of potentially the kind of connection you need at work. Large companies can feel overwhelming and it’s possible you’d end up feeling like one among many. If you prefer a place where you know all your colleagues much more closely and have a shorter line to impact, a small company might be more your thing.

👩‍🍳 What’s the leadership like?

There’s a common management adage: “People don’t quit bad jobs. They quit bad managers”. Whether that’s true or not is arguable but the impact a manager or in general, a leadership philosophy, is huge. This is why Glassdoor.com, among the very few things it measures, is “Approves of the CEO”. Do you align with the leadership style? Some managers are very hands on acting almost in the role of coach or mentor, whereas some managers are more focused on technical project management, playing less of a role in active career development. What do you want and need? It might not even be the “nice” boss!

🌱 Is it a startup?

A dream job can be a synergy between what a company needs and who you are: it doesn’t usually come out of the box perfect. More and more, we - both individually and as a part of teams - work together to shape our jobs by way of companies that enable this and encourage it. Startups, though not always and not exclusively, are recognizing that people have potential to keep growing and contributing, leading to (often accidental) professional development opportunities and environments where growth and change are constant.

Startups can be a great place to make an impact, build things, and experiment - but you may have to rely on self-learning, self-drive, even self-accountability more than a more established company that has its processes and structures more defined. They are known to be both exciting and volatile places to work, depending on where you go and what your tolerance or desire for risk and the unknown are.

🚂 What industry do you want to work in?

This is where the idea of “finding your passion” probably most closely aligns (but notice it’s still just one of the many factors). Is there a specific industry you’re interested in? If this is important, it helps to know because you might end up defining your dream job by industry more than you do by your role. Keep in mind that the most popular, “glamorous” industries are often the lowest paid, especially at the entry level.

But, something to consider: there are many roles and types of work available in any given industry, something that’s obvious but many of us don’t fully realize. So sometimes, we latch onto specific roles because they’re the most popular representations of a specific industry. For example, maybe you like movies. You don’t have to be an actor or director. Maybe you work in sound production for film, or costume design, or creative direction. This can be a great way to cast a wide enough net for something you’re passionate about but still have enough diversity in actual roles and companies; it can also be a great way to frame possible career changes.

🏷 What’s your role/title?

Is this important to you? If I can change your mind about the importance of not getting too stuck in on titles, it’s because they can be limiting. New jobs are being created all the time. But, if having a title that you feel proud of really matters for you to feel engaged, then fight for a job that reflects it. I’ve just seen a lot of titles that don’t actually fully encompass the role to put too much stock on this, but of course, that’s my biased view. What do you need? If you need clear definitions and responsibilities, are the job duties and responsibilities clear, and do they match up to what your title says? Vice versa: if you desire flexibility and agility and the thought of rigidity makes you anxious, then feel free to discard the importance of this. You might be the kind of person that applies to those “Define your dream job” postings that are popping up more and more now.

👓 What values and vision are you working towards?

More and more companies are taking this seriously, not just as an external customer value proposition point, but internally to inform and drive employee engagement. What do they say they believe in? Do you believe in that too? After all, you’re going to be contributing to that. Are there specific brands that really get you excited, even as a consumer? Pay attention to that! (…that is, if being highly aligned here matters to you. It might not! Or maybe it’s less important than other things.)

🖥 Where will you work?

Where do you do your best work? This often gets overlooked but it’s been gaining more attention in recent years with the rise of remote work. Remote work can take time to get used to and it’s a short pathway to isolation, if it isn’t done with care. And if you’re not self-motivated, you may find it hard to stay engaged especially at smaller companies. But do the benefits of zero commute and more control over how you work outweigh the cons?

I feel incredibly grateful to have been working remote full-time for about five years now. Before that, I had only worked in jobs where I was solo in a small, back office, which means I’ve successfully dodged my own personal work nightmare: open-plan offices, minus the occasional visit to company HQ. Don’t fall victim to what you think you should or shouldn’t want: I know someone who recently got a job with his very own cubicle, and it was his dream come true!

🚨 How much stress does the job come with?

Your job isn’t your whole life. What are your needs outside of work and how does your job potentially impact that? This is an interesting one because as it turns out, both in our tiny survey and in studies on careers, one of the key factors in a fulfilling career is challenging-enough work. There are many facets to this: Does the work feel too easy? Do you actually need more a challenge? The answer doesn’t have to be a resounding yes. Maybe you’re seeking something a bit more low-stress.

💰 How much money will you make?

Aside from all the warm fuzzies you get from jobs, the most tangible return on your time and investment is $. Studies show happiness doesn’t increase after we hit $75k in salary (take that with a grain of salt - 75k is a lot in some places, and not so much in others). What do you need to be happy? What are your life goals and how do your financial goals support that? Don’t settle in a job that otherwise is great if you can’t have what you need to live the life you want. Your life goals matter, a lot. That’s a big part of why you’re working. On the other hand, consider potential trade-offs in overall job satisfaction you may be making in pursuit of more money. Decide where your line is and what sacrifices you are, and aren’t, willing to make.

Across all industries, learning to negotiate, working hard and communicating your impact in performance reviews is important in increasing your earning power. P.S. We’re covering all things money here at SuperHi so stay tuned for more on that!

🎩 Does the name matter to you?

If working for the top of the top (insert with the FAANG or cool kid of your industry) is important to you, embrace that but make sure it’s not the default simply because you haven’t looked elsewhere. These jobs tend to be highly competitive, and probably for good reason. Working at a well-known company is huge for opening up opportunities. So it could make for a great dream job right now even if other aspects of the job are less than stellar, if it helps you get to where you want to go.

🍵 What’s the company culture?

There are a lot of amazing companies out there trying hard to make work work. They’ve figured out that if they want great work, it helps to create an environment where people can do their best work, a place they’re not always trying to escape from. Genius, isn’t it? The thing is, “great culture” differs vastly from company to company, even team to team. And it can be quite nuanced, hard to define. This is what defines your sense of belonging and connection in a workplace and it’s important that you feel in tune and aligned - so don’t discount the feeling of something just not feeling “right”.

👥 Who are you working with?

Do you like and/or respect your coworkers? This tends to get overlooked while you’re job hunting (because you don’t really know who you’re working with yet, in many cases), but one of the most commonly cited patterns that I’ve found in the people who talk about the jobs they love are that they enjoy the people they work with. Chemistry can’t be forced, but if you find yourself with a poor batting average when it comes to team fit, it might be worth some self-reflection too.

⏰ How much flexibility do you want?

This isn’t always the easiest thing to come by, especially if you’re just starting out and don’t have a lot of career leverage. Employers are more likely to trust you if you’ve got a track record. But it is becoming less of a rarity, as more employers realize that it can be a huge part of job satisfaction. Maybe your life demands flexibility, or maybe it’s a preference of personality. Just remember that flexibility can go both ways too - it’s easily a way to work more hours or feel like you’re working all the time. Do you like well-defined working hours where you don’t have to think about work as soon as you clock out? Or do you prefer a flexible approach?

💗 How important is growth and development?

We cover development opportunities and how to take advantage of them to grow your career and change jobs later on in this series. They can be a huge part of what makes up a dream job, if you thrive on being a constant learner and see work as a place to grow. What a company puts into their development and growth perks or programs can potentially be indicative of their general philosophy on work, growth, and how they invest back into their employees.

🥅 What motivates you?

Many companies have performance-based bonuses to help motivate and reward employees. In tech, equity and stock options or a combination of the two may be common. Are these important to you? Do you need to feel attached to outcomes in order to work at your best? If you identify as competitive or achievement-oriented, working at a company with an alternative compensation structure contingent upon performance can make a big impact in how you show up at work. There’s a reason certain people love sales, regardless of what they’re selling.

It may not be monetary: motivation can be intrinsic, like the above-mentioned growth, but there’s always ways to tie intrinsic goals into tangible achievements. If you’re a goal-oriented person, you might find yourself happier working at a company or in a job that has some sort of reward structure for performance.

👨‍⚕️ What benefits or perks are important?

We put benefits and perks last not because they’re least important, but because they’re a fairly obvious one. This tends to be a tangible one that companies love to outdo each other on. Make sure you’re clear on what you want and need, because this is one potential area that you may be able to negotiate if you need to compromise on something else on this list. This could include:

• medical insurance

• vacation policy

• professional development

• fitness and health

• pension and retirement savings

• coworking stipends if you’re remote

• catered lunch

• the list goes on!

Just don’t get too caught up in perks and realize that at the end of the day, they can usually be attached to a monetary value.

So what now?

How you turn this list into a “this is what I want and need from my dream job” will look very different. You may not even know right now, if:

• you’re new to work

• you’ve been disconnected from what you want for a long time

• you feel like the idea of a great job is a far-fetched fantasy

• you just haven’t tried enough versions of work

Here’s an example of how I think about my dream job: I value autonomy, and enjoy working with smart and talented people so that I’m not just self-learning (because I could do that myself). I value empathy more than I do perfection, and I prefer startup environments. I thrive on the feeling of not knowing what may happen, and riding the waves of growth and change to new things. I’ve been working remote for years and I don’t think I could go back, though it’s possible (but not likely) that I’d consider it. And I need to work for a company that I believe in and that feels like an extension of what I actively want to build and contribute to. So I only ever apply to jobs at companies that I think are the best at what they do, or could be, with a vision of the future that matches mine. And sure, sometimes I brag about my perks and vacation policy, but it’s really the work, team and culture that I’m here for. And, more on this in part four, but it took me a while to fully be aware enough to understand what I needed. I started without a lot of things, and built my dream career, one job at a time.

What I’m not doing: going through the list and ticking off the boxes, yes or no. The list is so you see the things you may not have previously considered, in light of being attached to the other surface components of jobs, then to use that awareness to gauge curiosity and exploration. But you have to rely on your gut to feel out what’s important, what’s priority, what really matters and what’s just a nice-to-have.

Knowing what’s out there and the various factors that make up what a job is, I hope, will give you something to reach for or at least be curious about other than the typical denominators we gravitate towards - or the one, grand “quit my job and travel the world” story we buy into of ultimate happiness.