Consider a scenario: You’re reentering the job market. You may have a few years under your belt or many years of experience, may or may not have a family, have some flexibility about where you want to work, and are trying to set yourself up for personal and professional success. Whether you’re an accountant or recruiter, CEO or marketing specialist, you’re trying to identify your next challenge and understand where you’ll add the most value and what you need to thrive at work. You have the luxury of picking from more than a few options and recognize that each person has their own definition of success. You’d like competitive compensation with long-term upside, but also the opportunity to network and skill build in order to maximize your lifetime earnings power. 

If this scenario sounds familiar, one of the key questions you are going to have to ask and answer is whether you want to work for a large, well-resourced brand name company or a smaller, less structured, high potential operation that runs a little leaner.

Two Roads Diverge

Large vs. Small is only one way to frame your search, but we think it’s an important one. We’re a small firm ourselves, and we invest in small businesses, so we’re frequently championing small over big. Put simply, we’re a team of people who all chose to work for a small company that buys and invests in small companies, so we self-selected into small. That said, there are many valid and right reasons for choosing to work at a BigCo, challenges involved in working at a SmallBiz, and vice versa. And that calculation looks different for everyone, regardless of whether you’re an entry-level worker or a CEO. Size drives a lot of the differences between companies that end up being most meaningful on a day-to-day basis.

The real work, then, is triangulating where you best fit. And that requires a lot of introspection and self-knowledge about what you value, what you’re good at, and where you want to go. It’s important to know yourself – is a defined role really a benefit for you or a tendency towards bureaucracy really a problem for you? 

Career decisions are difficult because they’re never really just about the job. They’re about how you see yourself, how you want to see yourself, the environment you want to spend at least a third of your life in, how you find meaning in work, and how you provide value and impact.

Which Has the Better Claim?

In the spirit of that messy middle, we’ve built a question set to aid in figuring out where you might find your best fit based on your skills, mindset, preferences, and goals. The answers are a sliding scale between one extreme and the other. One side is generally more common in large companies and the other is generally more frequently seen in small businesses, although of course nuances and outliers exist everywhere. While these questions may not seem exceptionally brilliant or groundbreaking, we do think they’re questions worth asking. 

If you’re seeking contentment and purpose in work, don’t game your answers because you think you should want to work somewhere or other (this is one reason among many why pro/con lists are less than effective – your pros tend to be aspirational and your cons delusional). Honestly assess what matters to you now and what matters to where you want to go. As in most things, you’ll tend to fall somewhere in the middle. 

We’re including some commentary with each question – in essence, the bulk of the article is contained inside. Ultimately, these are deeply personal considerations, and they’re heavily dependent on your values, life/career stage, and goals. A deep understanding of how you work and why you work is critical for understanding where you’ll prosper. Everyone has a right seat, whether it’s at the right hand of David or on the shoulder of Goliath.

Generally speaking, if your answers trended toward the left side of a scale, your fit is more likely to be found in a larger company. If your answers skewed toward the right side of the scale, you’re probably going to find more satisfaction in that area at a smaller business. Running the numbers, if your total score is under 20, consider big; over 40, think about small; between 20 and 40, you’ll have to do some digging on the specifics of role, company culture, team dynamics, and you.

Of course there’s nuance, and this scale doesn’t hold true in all cases for every employer. Plenty of large companies have axed full departments on a Friday and more than a few small companies have developed rigid hierarchies. If you take the general trends, though, and figure out where your skills, goals, and priorities lie, you’ll have an orientation to guide your decision-making.

You Can Do Both

There’s also a big asterisk on all of these questions. You’re allowed to change your answers.

“Right fit” might also change over the course of your career. In fact, it probably will as your priorities, goals, and time horizon shift. Your answers can change with money, time, health, priorities, kids, pets, hobbies, burnout, and bandwidth. And you’re allowed to try both. 

We all know someone who started out ready to take on the world at a mission-driven bootstrapped organization with long hours and great camaraderie who found themselves looking for more stability, better benefits, and a clear work schedule. Or someone who set out to make money and train up their skills who decided they were ready to move to the C-suite, but wanted an environment with more responsibility and fewer constraints. Operators who have done both tend to be well-rounded – and they can identify positives and draw from experiences at both types of companies.

 And know, too, that any industry, role, or geography can be found in both BigCo and SmallBiz. Cheerleaders and mentors and assholes are sprinkled throughout organizations of all types and sizes. There are small businesses that offer up opportunities to spend time abroad and big companies that never let you leave campus. If you take these questions about fit as your starting point, you’re on the path to understanding whether you want to be a part of scale or contribute to meaningful alternatives.

So we hope these questions are useful as a resource, a reminder, and a jumping off point to better understand how your goals, expectations, and values intersect with company size and structure. We also, as always, hope you’ll consider small. But only when it’s the right fit.

Is small the right fit for you? Join the Orbit to connect with opportunities.