Category Archives: <a href="/topic/business"><span itemprop="about">Business</span></a>

Matt Griffin on How We Work: Balancing the Scale

Posted by The fine folks at A List Apart |11 Nov 15 |

Where do you work? The term you choose to describe this place—consultancy, studio, shop, agency, freelancer—is in some ways a roll of the dice. It’s an aesthetic decision as much as anything else. But it can also say a lot about the culture of the business. For instance, where are your offerings on the spectrum of fields like advertising, design, software development, and user experience? I’ve listened to people emote emphatically about what is a shop and what is an agency, assigning pride to one and derision to another.

Another thing those terms imply, to some degree, is scale. No one’s going to advertise their 50-person freelancer, for instance. Likewise the proclamation of a 2-person agency will no doubt elicit a few snickers from the crowd.

But feelings aside, is there a real correlation between some of the qualities we use to measure a workplace (capabilities, cultural traits, limitations) and its size? When we’re trying to figure out where to work, or how we want to develop our own business, might we be able to make some value judgements based on scale?

To help make this a little clearer, I talked to some friends who have been in a variety of situations. Some of them started small and grew their businesses. Others went the other direction. Let’s see if we can figure out why.

Go big or go home

I myself am the founder of a place that has grown over the years, albeit very gradually and in small increments. We started Bearded in 2008 with two people, and are now at seven after as many years. Now by most standards we’re still pretty small, but the differences between 2 to 3 and 6 to 7 people can be quite striking.

As a two-person business, anything that had to be done was done by one of us. Thus we wore a lot of hats. My major roles were that of designer, salesman, and project manager. My business partner’s were mostly that of web developer and operations. And then there were the myriad less-glamorous tasks we’d split up, like mopping the floor or harassing the landlord to get the electricity turned back on after the breaker in the locked basement blew for the third time that week (true story).

At that point, we had only a dim awareness of many of the skills and processes that I now see as integral to successful web design. As we hired new people, we found we weren’t just adding staff that duplicated our existing skill sets, but bringing on folks whose expertise complemented our own. These new folks helped us create better products for our customers.

Our new hires brought in skills like illustration, custom application development, animation, content strategy, information architecture, user experience design, and business development. Though you might expect this would broaden our offerings, it actually did the opposite. We added people and skills, but somehow our focus grew narrower. Those added skills allowed us the expertise to solve more complex problems in more specific areas. We stopped being a general design shop, refusing projects like logo and stationary designs. Over time we matured into a web consultancy focused on user experience in a multi-device world, through the lens of progressive front-end development.

Ben Callahan had a similar experience with Sparkbox:

The biggest benefit to having a larger team is that we can allow people to specialize a bit more. For example, as a front-end dev that’s transitioned to the role of president, I can focus on leading our company instead of writing code. When we were smaller, everyone did everything. This focus lets us go deeper in specific areas.

For Bearded, that small amount of growth deepened our expertise and allowed us to shed what were, to me, the least interesting things we did. It allowed us to focus on what we’re best at—what sets us apart from others. In the process, that also made Bearded a more satisfying place to work.

What you can do with more

Quality of life and job satisfaction are important. But practically speaking, what are the advantages that you only find at scale?

Val Head’s previous experience in agency life felt full of knowledge and resources:

There were so many people with different strengths, background and knowledge. If there was something you needed to know you could pretty much find someone a few cubes over or on another floor who knew all about it.

Jeff Robbins, co-founder and CEO of Lullabot, tends to agree:

Being bigger has given us resources to accomplish more. We’ve been able to experiment with products and even improve our website in ways that were more difficult when we were a smaller company.

So in Jeff’s experience, Lullabot can do more with more people. But does more people mean that you can do bigger projects? Val Head puts it this way:

Larger businesses are better at handling a whole suite of related projects. Basically anything where having more people could make things go faster or more efficiently.

Todd Parker and Patty Toland spent some time at a very large agency before founding Filament Group, and they found that scale also really affected business development:

The upside of that large scale was that they hired really smart people and did insightful work for good companies who wanted to solve hard problems well, and with that scale they were able to secure contracts with bigger clients and get into rooms alongside serious Big Consulting firms, and compete.

Which is all great. But there’s a big (pardon the pun) aspect to scale that we haven’t broached directly yet, and that’s money.

It’s all about the Benjamins

Regardless of how you price your work, if you’re running a healthy business, most employees should do enough billable work to cover their own cost, plus generate a profit for the business.

Now as the business grows, there will likely be a need for some support staff—people who help the business run but whose work isn’t directly billable. Some examples are operations, sales, and administrative staff. Like office space or utilities, these positions tend to support some number of billable staff. This means that the more billable staff you can employ (hire and have work for) without increasing your support staff and other overhead, the more profit the business will be able to generate.

Though profitability tends to come in overhead-related tiers, the general rule is: the more billable staff you can employ, the more money your business can bring in. The real trick here being that those staff need to be doing billable work all the time. Which introduces a chicken and egg situation: if you hire staff and don’t have the work to justify them, you’re losing money. If you have to turn down the work you want to do because you don’t have the people to do it… that’s no fun either. And possibly worst of all is the option of taking on more work than you can reasonably handle, which will certainly get you into trouble sooner or later.

I’ve found that growth tends to be a balance between business development and hiring. When we’re in growth mode at Bearded, we tend to try to ride at the edge of the maximum amount of work we can do while actively looking for new hires. For instance, if our ideal workload is 3 full time projects, then we’ll shoot for 3 1/2 projects worth of work for a little while. That tends to be a nice stress test, giving us a good sense of which skill sets are overworked at that scale. When the right person comes along, we hire them. We might be a little suboptimal for a while in terms of workload and stress, but eventually we’ll add appropriate staff and settle in to our new ideal workload (maybe 3½ or 4 full time projects), and start the same cycle again when we’re ready.

Todd Parker and Patty Toland at Filament Group look at it this way:

Even though our growth has been minuscule and snail-paced, we have always and only grown when we’ve found a potential team member who is so incredible we just have to work with them. Jim Collins was right in Good to Great when he said having the right people on the bus is the most essential decision and everything else follows (or doesn’t). Our growth decisions are always built around people.

Sounds a lot like my experience. If you find just the right person to hire, it’s usually worth taking the hit on overhead until you can drum up more business. Good people are hard to find, and finding good people is one of the key ingredients to doing better work (and making more money).

Growing pains

So growing can be good. But growing a business is not without challenges.

Lullabot’s Jeff Robbins has some interesting thoughts on the pains of scaling:

I’ve got a theory that company growth inflection points happen at the powers of 2. Going from 1 person to 2 is a challenge. At the point where you have 4 people, the company is getting serious. When you’ve got 8 people, you begin to feel the responsibility. At 16 people, you’re legitimate—and there’s no going back. The 16 to 32 person stretch is also where you need to start thinking about management structures. At 32 people, you start to think about the needs of the company rather than just the individual people. Your trees have become a forest. You start thinking about things like “systems” and “process.” We’re on our way to 64 people. This is where people start losing track of each other. They don’t feel like they “know” everyone at the company and they don’t speak up and contribute as often because they assume that they can’t make an impact at a company of this size.

From Jeff’s experience, there are always challenges and opportunities at any size. Each situation must be solved for to progress to the next. Growth, in other words, isn’t all tripping through the daisies.

More people, more problems

Ben Callahan notes that “the weight of a larger payroll is something that makes a larger size more stressful.”

And it’s not just the weight of the larger payroll, but also of the increased infrastructure. Todd Parker and Patty Toland explain:

Working within a larger organization always felt fraught with pipeline discussions: having a bench of idle people was stressful, and managing schedules when deadlines inevitably moved out was equally hard. Even with some incredible project managers, it was a balancing act that frequently required compromising (quality of work, ethics of clients, respect for employees’ personal lives and schedules) that wasn’t always comfortable.

Todd and Patty make a great point about the compromises that inevitably come about when you have a big payroll. I once spoke with a former partner of an agency that had ~$1M monthly overhead. At some point she had to choose between taking work from an apparel company in the midst of a sweatshop scandal, or laying off staff. She chose to work with the apparel company and keep her staff employed, but it wasn’t long before she exited the company because of this kind of ethical conflict.

Sparkbox’s Ben Callahan adds that larger organizations’ agility can sometimes suffer in other ways, as well:

Smaller teams also require a little less process—having everyone in the same room can unintentionally assist in your organization’s communication. And, there’s something freeing about being small—[at Sparkbox] we try to retain all the benefits of being small, but it’s never quite the same.

So it sounds like that increased infrastructure—that same thing that gets you all those extra resources that people like—can potentially become a liability. Coordinating all those people is difficult, and takes a significant amount of time away from other tasks.

Regardless, Jeff Robbins has found that at Lullabot they’ve always been able to overcome the challenges that arise:

I see growth as a creative endeavor. It’s problem solving. We used to say things like “if we grow any larger than this, the company isn’t going to be as good.” But we kept asking ourselves “why do we believe this?” And eventually we’d come up with creative solutions which would allow us to grow without losing the things we loved about the company. The growth brought with it more creative possibilities and capabilities.

For Jeff, growth’s problems can be overcome. But some others don’t see much in the way of benefit for larger organizations. Brad Frost doesn’t agree that larger teams are better at bigger work:

I can’t even say that a larger scale of work can only be accomplished by a larger team, as I’ve seen time and time again that small teams can do amazingly complex work given the time and autonomy to do so.

And I’ll be damned if that isn’t a nice segue into the benefits of smaller teams!

Let’s get small

Not everyone wants to work at a large business. In fact, lots of folks seem to depart from large businesses with the goal of working somewhere smaller, or even on their own. Someone who’s left the larger agency world to go out on his own is G. Jason Head:

In a larger agency setting there are a lot of titles and seniority levels that need to be addressed. Sometimes, it’s completely valid, but a lot of times it’s also stroking people’s egos. It’s just sort of the reality of agency life.

I like not having half of my day being eaten up by meetings. I like being able to really focus myself on my development work. My concentration is so much better [since going solo], and I honestly think I am doing some of my best work.

Brad Frost has of late done some rather high profile work as part of small ad-hoc teams, and he thinks the benefits are overwhelming:

I absolutely love the momentum that comes with working with a small group of smart, autonomous people. You’re able to collaborate easier, solve problems faster, and get things done without the layers of bullshit that inevitably come from gargantuan teams.

You can go your own way

If you get small enough, you become the owner by default. And it seems like there’s a certain amount of overlap between those who want to work smaller and those who want to be in charge of their own destiny. Todd Parker and Patty Toland of Filament Group have something to say about this:

I think the biggest advantage of being small is the ability to say “Yes” and, more importantly, “No” to the opportunities that pass our desk, and having more control over scope, schedules and terms of working relationships we commit to. With our small team, we can only take on a certain number of projects at a time, so we try to be careful to make sure they’re going to be the best use of our time, that we are the best fit with the most appropriate skills to deliver value for our clients, and that we take on the most interesting opportunities to learn, build our skill sets and promote ideas we think are important.

Weighing those sorts of decisions, choosing whether or not to compromise, is something you don’t generally get to do when you’re not holding the reins. I remember someone talking to me about this issue a number of years ago when we were even smaller, and my response then was that because Bearded was small and had a low overhead, it was easier to turn down problematic-looking work.

That is in some ways true, but I don’t think it’s just the amount of your overhead that ties you down. Similar to the difference between revenue and profit margin is the cost of your overhead as compared to your overall potential project revenue. If you have a $1M monthly overhead, but you have, on average, $2M worth of plausible work that wants to sign every month, then you’re in a pretty safe position as far as picking your projects goes. But if you grow to meet your average potential work, then you don’t get to be so choosy. You have to take every project that shows up at your door, like it or not.

What shall we do?

So what’s better, big or small? Owner or employee? Only you can answer that question. In reality, there are as many variations for a business as there are people to start them.

The question to ask yourself is: what do you most want to get out of your work? If you like having access to a variety of skills and extensive resources, then you might need to get bigger.  If agility or a lack of bureaucracy is what you’re after, then perhaps smaller teams are a better fit. If you’re at a point where you’re looking to make more money, then it may be time to grow bigger. But if being choosy about clients and projects sounds compelling, maybe a smaller crew with less overhead is what you need.

Now it’s likely that most people care about all of those things to some degree. But what’s most important to you? It’s almost assured that you spend as much time working as you do anything else. And no one can ever pay you enough to hate that time—your time on earth. So make sure that, whatever your choices, they help create an environment that makes those days more satisfying.

Antoine Lefeuvre on The Web, Worldwide: Singapore, a Hub for Designers?

Posted by The fine folks at A List Apart |05 Nov 15 |

One of this column’s objectives is to take you traveling. Our destination today is the city-state of Singapore. During my voyages, I kept coming back to this small Asian nation, because Singapore is a hub for world travelers. But is it a hub for designers too? Here’s the answer from three Singapore designers—two expats and one local.

The Lion City

I first traveled to Singapore in 2010, my mind full of stereotypes: I expected to find a postage stamp-sized country—think Vatican—so aseptic that even chewing gum is illegal. But I quickly realized how wrong I was. Singapore is actually a 30-mile-wide island blessed with lush vegetation and home to a thriving city of 5 million inhabitants. Only 60 percent are Singaporean citizens, including Amalina Zakaria, a web designer “born and raised in Singapore” who represented her country at WorldSkills 2009.

The Lion City—Singapura in Malay—is also a hotspot for expatriates. Game designer Antoine Henry left the banks of the Seine for the shores of Malacca Strait in August 2014. In the growing expat community he met Perrine Lefeuvre, a creative director who has been working in Singapore since 2012 for luxury brands such as Guerlain and Hermés.

One of the notions I had about the city turned out to be true. Singapore is “Asia for dummies”—an easy city for first-time travelers to Asia: orderly, English-speaking, clean, well-connected. Easy doesn’t mean boring, though. The whole of Asia meets in the city-state.

View of traditional and modern architecture in Singapore.

A unique blend

“The cultural diversity here is one of my main sources of wonder. For a European like me, it is amazing to find yourself at the crossroads of Asian cultures like Chinese, Indian, Malay, and the whole diversity of South-East Asia in general,” says Antoine Henry. Perrine Lefeuvre also finds that the city-state is an exciting place to be a designer. “If you have experience, you will have access here to projects you will never work on in Europe.”

Even for those who are not new to this melting pot, like Amalina Zakaria, the diversity is mind-opening. “The different styles of each culture and how it is fused and integrated into modern design has always been an inspiration for me as a designer.”

With 75 percent of Singaporeans being ethnic Chinese, you might be tempted to imagine the Lion City as a microcosm of China, a tropical Hong Kong. “Don’t,” reply my three interlocutors as one. “Despite our large Chinese population,” says Amalina Zakaria, “we are ultimately a Singaporean audience, rather than a Chinese, Malay, or Indian audience.” Perrine Lefeuvre adds, “Singapore only feels like China during Chinese New Year, when everything is gold and red—the traditional colors.” She even believes there’s a Singaporean style of design: “Very preppy, gentle, clean—and a bit hipster.”

The right environment for creatives?

Many web, game, and design companies have chosen the city-state for their Asian headquarters, Perrine Lefeuvre told me. And startups are following suit. “With a growing entrepreneurial spirit among locals, this creates opportunities for creative professionals to work with startups on exciting new projects. There is a lot of financial support and backing in the form of grants if creative professionals want to start something,” says Amalina Zakaria. “Singapore is a booming industry for creatives,” she adds.

Singapore, a paradise for startups and web companies? Although Amalina Zakaria has found bureaucratic procedures stifling, Harvard Business Review calls Singapore “one of the easiest countries in the world in which to do business.”

But when it comes to recruiting creatives, most of the expats I met told me the process of fostering creative thinking needs more time. A tradition of putting the group in front of the individual has historically made local workers less comfortable displaying initiative and creativity. “After a few frustrating experiences, I had to hire a designer from the Philippines because I couldn’t find one from Singapore,” explains Perrine Lefeuvre. Antoine Henry, who leads a team of designers, also experienced the culture gap. “I was used to challenge and be challenged quite openly regardless of who’s managing who. This is happening a lot less here, and I had to change my work process to actively seek that kind of honest feedback.”

A genuine world city

Listening to Antoine Henry, I have the feeling Singapore is actually Asia’s biggest Western city. “From my colleagues’ gaming habits and the test sessions we conduct with Singaporeans, I tend to think that their video games consumption is closer to Western than Chinese.”

Singaporeans are “exposed to a lot of influences from the West right from the start,” explains Amalina Zakaria. “We may be struggling to inject more Eastern influences into our work!” she adds. Which means designers choosing the city-state for a deep dive into Asian cultures might be in for a disappointment. “It doesn’t have the hints of Asian tradition that you find elsewhere in South-East Asia, nor the eccentricity found in South Korea or Japan,” acknowledges Antoine Henry.

But Singapore is actively shaping its own culture. This could well be its best argument to attract foreign clients as well as creative workers. As Amalina Zakaria says, “designers in Singapore are so well-versed in Western media, culture and customs, that we’re able to communicate effectively with our global clients.”

Because it concentrates so much diversity, Singapore has always struck me as an “East meets West” kind of place. “It’s a more complex situation than just ‘East meets West’,” retorts Amalina Zakaria. “We do not have a long history that is unique to ourselves,” she says. “However, we are globally exposed with a lot of influences coming from outside, rather than inside—and that’s what makes us globally competitive.”

Rachel Andrew on the Business of Web Dev: Software Audits for the Tiny Business

Posted by The fine folks at A List Apart |02 Jul 15 |

In the dot com boom, I headed up a technical team. One of my responsibilities was the hardware and software needed by our team and other teams in the company. Back then, software was typically boxed and came with packs of licenses. I had an internal software audit routine to check that all of our computers were correctly licensed.

In my own business, I’m part of a two-person team. Many of our software licenses are purchased far less formally and are for one user only. We also rely on a huge amount of Software as a Service, where there is no box or permanent license to use the service. As owner-managers, we sometimes buy something using a personal email address or bank card, despite it being for company use. Also, we contract third parties to do work for us, and they purchase software or create accounts on our behalf. With no physical boxes, or volume licenses to keep track of, small companies now develop websites and software in a far more informal way.

It’s a common pattern we see at Perch: the company contacting us has had a website developed, and sometime later the person who developed the site and bought the software license leaves the company. The company has no idea how to access the license information, and password reset attempts go to a now-dead email address. Sometimes the account is linked to a personal email address, or was even bought by a third party who had been contracted to build the site.

With accounts spread around between owners, employees, and contractors, businesses can easily leave themselves exposed. Services get canceled because no one saw the reminder that a credit card had expired. Domains fail to auto-renew, leaving the company in danger of losing them. Software purchased via an employee or contractor becomes inaccessible due to that person leaving. Therefore, I propose that every business needs a software and services audit. Collate all of this information, then make sure it is accessible to you and other trusted team members.

What should we audit?

What should you take a look at? To get you started, I’ve listed a few key areas that most web agencies and software businesses will recognize. Once you start this process, you will no doubt think of more. (If you think of something other business owners might forget, add it to the comments.)

Domains and DNS

Does the company own all of the domains you use, or are any linked to personal accounts?

Can you move all of the domains and DNS management to one location? Services such as DNSimple offer domain hosting and DNS management, and can be a better choice than having domains registered alongside your webhosting.

Do you have a solid way to track expiration dates? Are domains set to auto-renew with up-to-date payment details? Do all of the domains have correct contact details?


How many email accounts are being used in your business? Are you, or your employees, using personal addresses for company business?

Is important and valuable information stored in your email, or in the email of employees? For example, if you work with clients by email, who has the history of the conversations?

Is email securely backed up?

Software used on your websites

Many websites rely on paid software-whether that is a full CMS like Perch, or paid add-ons to WordPress. Who owns those licenses?

Which email address is linked to these licenses? The developer might use it to let you know of important security updates to the software.

Do you have access details for any account on the third-party website?

Do you know where and how to get support for any of the components of your website that haven’t been developed in-house?

If you develop websites for clients, you may be able to help them to manage this better by providing a handover pack on payment that includes all of the key details and clarifies their significance.

Recurring payments

Go through your bank and card statements. What does your business pay for, monthly or yearly? Cancel anything you don’t use.

For services you do use, check if you can save money and bookkeeping by switching to an annual plan.

Check that the plan you are on is up to date and still the right one for you. SaaS companies often introduce new levels of service—you might save money or get new functionality by switching.

Keep a list or spreadsheet of services and the date on which you last checked them. You can repeat this process every six months, to make sure you don’t pay for things that you are not using.

Start with one small thing

Auditing everything you use in your business is likely to save you time and stress in the long run, but with our limited time it’s an area we can find easy to avoid. You don’t need to do this all at once. Next time you have a couple of spare hours, pick off one area and start there.

In a couple of hours you could list all of your domains, check when they expire and make sure that you can access the registration for each. You may need to add another to do to your list to consolidate them at one provider, or to update contact details. However, you have moved forward just by knowing what the status of your domains is. You are already less likely to have the nasty surprise of waking up to find a website offline due to the domain expiring.

Let me know in the comments if this is an area you struggle with; or if you have found good ways to store, maintain, and share this kind of information.

Ask Dr. Web with Jeffrey Zeldman: If Ever I Should Leave You: Job Hunting For Web Designers and Developers

Posted by The fine folks at A List Apart |30 Jul 15 |

In our last installment, we discussed what to do when your boss is satisfied with third-party code that would make Stalin yak. This time out, we’ll discuss when, why, and how to quit your job.

When is the right time to leave your first job for something new? How do you know you’re ready to take the plunge?

Wet Behind The Ears

Dear Wet Behind:

From frying an egg to proposing marriage, you can never know for sure when it’s the right time to do anything—let alone anything as momentous as leaving your first job. First, search your heart: most times, you already know what you want to do. (Hint: if you’re thinking about leaving your job, you probably want to.) This doesn’t mean you should heedlessly stomp off to do what you want. Other factors must be carefully considered. But knowing what your heart wants is vital to framing a question that will provide your best answer.

So ask yourself, do I want to leave? And if the answer is yes, ask yourself why. Are you the only girl in a boys’ club? Perhaps the only one with a real passion for the web? Are other folks, including your boss, dialing it in? Have you lost your passion for the work? Are you dialing it in? Is the place you work political? Do your coworkers or boss undervalue you? Have you been there two years or more without a raise or a promotion? Most vital of all, are you still learning on the job?

Stagnation is fine for some jobs—when I was a dishwasher at The Earth Kitchen vegetarian restaurant, I enjoyed shutting off my brain and focusing on the rhythmic scrubbing of burnt pans, the slosh and swirl of peas and carrots in a soapy drain—but professionals, particularly web professionals, are either learning and growing or, like the love between Annie Hall and Alvy Singer, becoming a dead shark. If you’ve stopped learning on the job, it’s past time to look around.

Likewise for situations where you face on-the-job discrimination. Or where you’re the only one who cares about designing and building sites and applications that meet real human needs, and of which you can truly be proud. Or where, after three years of taking on senior-level tasks, and making mature decisions that helped the company, you’re still seen as entry-level because you came in as an intern—and first impressions are forever. Or where you will never be promoted, because the person above you is young, healthy, adored by the owner, or has burrowed in like a tick.

Some companies are smart enough to promote from within. These are the companies that tend to give you an annual professional development budget to attend conferences, buy books, or take classes; that encourage you to blog and attend meet-ups. Companies that ignore or actively discourage your professional growth are not places where you will succeed. (And in most cases, they won’t do that well themselves—although some bad places do attain a kind of financial success by taking on the same kinds of boring jobs over and over again, and hiring employees they can treat as chattel. But that ain’t you, babe.)

It’s important, when answering these questions about your organization and your place within it, to be ruthlessly honest with yourself. If you work alongside a friend whose judgement you trust, ask her what she thinks. It is all too easy, as fallible human beings, to believe that we should be promoted before we may actually be ready; to think that people are treating us unfairly when they may actually be supporting and mentoring us; to ignore valuable knowledge we pick up on the job because we think we should be learning something different.

If there’s no one at your workplace you can trust with these questions, talk to a solid friend, sibling, or love partner—one who is brave enough to tell you what you need to hear. Or check in with a professional—be they a recruiter, job counselor, yoga instructor, barista, or therapist. But be careful not to confide in someone who may have a vested interest in betraying your confidence. (For example, a recruiter who earns $100,000 per year in commissions from your company may not be the best person to talk to about your sense that said company grossly undervalues you.)

Assuming you have legitimate reasons to move on, it’s time to consider those other factors: namely, have you identified the right place to move on to? And have you protected yourself and your family by setting aside a small financial cushion (at least three months’ rent in the bank) and lining up a freelance gig?

Don’t just make a move to make a move—that’s how careers die. Identify the characteristics of the kind of place you want to work for. What kind of work do they do? If they are agencies, what do their former customers say about them? If friends work for them, what do they say about the place? What’s their company culture like? Do they boast a diverse workforce—diverse psychologically, creatively, and politically as well as physically? Is there a sameness to the kind of person they hire, and if so, will you fit in or be uncomfortable? If you’d be comfortable, might you be too comfortable (i.e. not learning anything new)? Human factors are every bit as important as the work, and, career-wise, more important than the money.

If five of your friends work for your current employer’s biggest competitor, don’t assume you can walk across the street and interview with that competitor. The competitor may feel honor-bound to tell your boss how unhappy you are—and that won’t do you any good. Your boss might also feel personally betrayed if you take a job with her biggest competitor, and that might be burning a bridge.

Don’t burn any bridges you don’t have to. After all, you never know who you might work for—or who you might want to hire—five years from now. Leaving on good terms is as important as securing the right next job. Word of mouth is everything in this business, and one powerful enemy can really hurt your career. More importantly, regardless of what they can do for or against your career, it’s always best to avoid hurting others when possible. After all, everyone you meet is fighting their own hard battle, so why add to their burdens?

This isn’t to say you don’t have the right to work for anyone you choose who chooses you back. You absolutely have the right. Just be smart and empathetic about it.

In some places, with some bosses, you can honestly say you’re looking for a new job, and the boss will not only understand, she’ll actually recommend you for a good job elsewhere. But that saintly a boss is rare—and if you work for one, are you sure you want to quit? Most bosses, however professional they may be, take it personally when you leave. So be discreet while job hunting. Once you decide to take a new job, let your boss know well ahead of time, and be honest but helpful if they ask why you’re leaving—share reasons that are true and actionable and that, if listened to, could improve the company you’re leaving.

Lastly, before job hunting, line up those three months’ rent and that freelance gig. This protects you and your family if you work for a vindictive boss who fires employees he finds out are seeking outside jobs. Besides, having cash in the bank and a freelance creative challenge will boost your confidence and self-esteem, helping you do better in interviews.

A good job is like a good friend. But people grow and change, and sometimes even the best of friends must part. Knowing when to make your move will keep you ahead of the curve—and the axe. Happy hunting!