Chase was looking for freelance design work. When a friend introduced him to an event coordinator who needed a good designer, Chase jumped on the phone with his prospective new boss. The way he tells the story, he instantly knew that the situation would be a disaster.

The event coordinator was cagey, skeptical, and vague about what what he needed for his upcoming events. He challenged Chase to pitch ideas without giving him much context on his brand and clients. When Chase tried to ask questions, the guy insisted he needed a designer who had enough experience to figure out what he needed without much guidance, which is pretty much every designer’s nightmare.

“Get back to me this week,” he said. “I need someone to start right away.”

So, not exactly an inspiring conversation. Chase pretty much decided on the call that he was going to pass on the job. The only problem was that his friend had talked him up quite a bit — and had been close colleagues with the event coordinator for years.

Meanwhile, the coordinator was chasing him pretty hard — he had sent two emails in the last few days asking when Chase could start.

Now he was in a tough spot. If he turned down the job, he risked compromising his friend’s relationship with the event guy. If he took the job, he’d be compromising his own integrity and jumping into a dysfunctional situation. Chase was asking himself a question we all confront at one point or another: How do I say ‘no’ without looking like a jerk?

That’s what we’ll be talking about in this piece: the art of declining offers, turning down opportunities, and avoiding situations in a way that protects your social capital, and can actually help enhance it.

The first step?

Decide if this is an opportunity you actually want to decline.

Some decisions — like Chase’s offer from the coordinator — are no-brainers. In the course of your career, you’ll encounter no shortage of needlessly stressful work environments, hopelessly dysfunctional friendships, or obviously incompatible partners. In those cases, you’ll know on a cellular level that declining the offer is the right thing to do.

Most opportunities, though, are much more ambiguous. Potential jobs are stressful and exciting, first dates are intimidating and promising, big trips are daunting and inspiring. In those cases, we need to sort through several different variables to arrive at the right decision.

Of course, every scenario is unique, and every person is different. But a key stage in this process is understanding whether your ‘no’ is based on sound reasons, or just an instinctive desire to avoid change or ambiguity. We all wrestle with this tendency to some degree because the human mind is inherently conservative and tends to protect itself from uncertainty.

So before you decide to turn down an offer, ask yourself if this new opportunity, conversation, or relationship could help create a brick in your wall. Would saying ‘yes’ create a new relationship or add to your social capital? Are you saying ‘no’ reflexively, or because you’ve really figured out what you and the other person really want? Could a simple ‘yes’ add to your talent stack?

After a few major careers, dozens of side hustles and hundreds of interesting conversations, I’ve learned that the random ‘yes’ — at least to a brief conversation, which usually has a pretty low cost — can be far more powerful than the immediate ‘no.’

But if you definitely want to turn down an opportunity, then…

Communicate openly and respectfully.

In today’s culture, ghosting, avoiding, or vaguely dropping off has become more and more common. That might be de rigueur in today’s transactional dating and online business world, but when it comes to more meaningful decisions — especially professional ones — I recommend communicating directly and honestly.

Once you decide to turn down an opportunity, consider writing a brief note to your point-person explaining your decision. This kind of open communication isn’t just respectful — it’s also precisely the kind of move that preserves and even builds social capital.

In your note, briefly explain why you’re turning down the opportunity, keeping the reasons primarily focused on yourself. Of course, the rules of diplomacy and decorum apply — you wouldn’t decline an unattractive job offer by calling the hiring manager a shiftless tool — but you can trust that brief, respectful honesty will serve you well.

In many cases, you can frame your decision as a favor to them — because ultimately, it is. If you decline a position that would have made you miserable, you aren’t doing right by the hiring manager who deserves an employee who truly wants to be there.

Chris, a recent AoC bootcamp grad, once sent a “thanks, but no thanks” email to a hiring manager that accomplished this masterfully.

“At this stage in my career,” he wrote, “I’ve learned to trust my instincts about which cultures are a good fit for my skills and personality. You deserve someone who can give you a hundred percent of his confidence and ability, which is why I feel I should continue my job search. Given the role, I’m sure you’ll find a great candidate very soon.”

It doesn’t get much classier — or more diplomatically honest — than that. He didn’t dwell on all his concerns, but he didn’t sugarcoat them, either. In a world where people lie or obfuscate when they decline an opportunity, a respectful ‘no’ goes a very long way.

Of course, some situations don’t require this level of diplomacy. If a hiring manager, vendor, or date has acted egregiously — either by being disrespectful, inappropriate, manipulative, or straight-up creepy — then you’re almost certainly off the hook. These are a few common scenarios in which dropping off is truly acceptable — generally when the other person has compromised your social capital, or has shown a total disregard for their own.

In all other scenarios, take the time to explain your decision, but…

Decide when to expand on your ‘no.’

Honesty is important, and can actually enhance your relationships when it’s used effectively. But some people can take the previous principle a bit too far, and use their ‘no’ as an opportunity to give a difficult person a piece of their mind. This can be tempting, especially in unpleasant situations, but it rarely pays off.

Chase, for example, would have loved to tell that event coordinator that his personality made it impossible for him to accept the job. He ultimately didn’t, and not just because they had a mutual friend. He simply recognized that there was no clear upside to articulating his concerns, and little chance that the coordinator actually wanted to hear them. I’d say that holds true for 95% of contentious interactions.

If the other person asks you to explain your decision further, however, then the calculus changes. In that scenario, check in with yourself one more time, and decide whether sharing more feedback would be in service of the other person — for example, explaining what you found lacking in a job offer so a hiring manager can try to fix it — or just an opportunity to make yourself feel better.

Brent, a long-time listener of the podcast, recently found himself on an interesting side of this scenario. When a gal he had been on two dates with texted him to say she wasn’t interested in pursuing their relationship, he decided to take a chance and ask her if he had done something wrong.

In her response, she explained that she just didn’t feel a connection with him, but that the way he talked about his job might have played a role. It was the first time Brent had heard that observation, and it helped him realize that his recent frustration with work was coming across the wrong way on first dates. He recalibrated the way he talked about his stressful job with new people — avoiding any bitter or unpleasant commentary about the company — and said it actually helped him notice the negative thoughts he was carrying around about work in general.

In that situation, expanding on the ‘no’ was a productive conversation for both parties. Brent really wanted to have a better picture of himself, and approached the conversation with an open and nonthreatening way. At the same time, his date didn’t use the opportunity to put him down or make herself feel better after ending things. When Brent heard the feedback, he used it to address the problem, and said his dates have had a much better energy since. He and the gal are still friends, which Brent attributes to the fact that they approached each other with a refreshing openness from the start.

So as you navigate these decisions, decide whether a simple “thanks, but no thanks” is the right move, or whether passing along some more information would be productive. You’re rarely obligated to say more when you decline an offer, but some scenarios really do benefit from additional feedback.

Of course, anyone open to hearing more feedback is probably someone who cares about their relationships and social capital. And when you come across that sort of person, then it’s worth considering how to…

Find a way to help anyway.

Having interviewed some of the greatest networkers in the world, I’ve found that most of them share an interesting quality: they always look for a way to help the people they meet, even — and especially — when that help isn’t expected.

My friend Mason, for example, recently made the jump to a new law firm. During the job hunt, he interviewed at a dozen places, got offers from about half, and ultimately landed at his favorite. But when he wrote emails to the other six firms declining their offers, he took an extra moment to ask them a simple question: “Would it be helpful to send some other good candidates your way?”

The answer from every single firm was ‘yes.’ They were bummed not to land Mason, and they were always desperate for talent. Having spent a good 15 years as a lawyer, he knew dozens of attorneys looking for job opportunities. So it was a no-brainer for him to take an hour out of his week and make introductions to the right firms on their behalf.

The result? Four out of the six firms he declined ended up hiring at least one person he recommended. Talk about killing two birds with one stone! With that simple move, he softened the blow of his ‘no,’ then turned the end of a conversation into several new job offers for his friends.

This is pure strategic generosity in action. Because Eric actually liked the firms he was turning down, there was a good reason to help them out. And because Eric understands the importance of investing in the people around him, he took the time to be of service to his colleagues.

Eric literally turned a “thanks, but no thanks” into a social capital engine — just by asking himself how he could still help out those firms. He even checked in every six months to see how his colleagues were doing in their new jobs. In a few years, when Eric is ready to make a change or needs to work with one of those attorneys, you can imagine all the goodwill that will be waiting for him.

I’ve seen this principle work wonders in all sorts of scenarios. My friend Leslie, for example, once had a first date with an awesome guy she didn’t quite click with. Instead of just parting ways, she decided to introduce him to an old college friend, hoping they might hit it off. The two ended up dating for three years, and became a huge part of each other’s lives.

The very same principle works in our personal and professional lives. We can be of service wherever we go, even when being of service isn’t the obvious or expected thing to do. Which makes it much easier to…

Trust that ‘no’ can be one of the greatest tools in your toolkit.

Saying ‘no’ is never easy, and it’s rarely fun. We don’t want to hurt people’s feelings, we don’t want to miss out on opportunities, and we generally want to avoid the awkwardness of conflict.

And yet we know that our success depends on saying ‘no’ to the wrong opportunities so we can say ‘yes’ to the right ones. Ironically, the better we become at our jobs, our lives, and our relationships, the more opportunities we generate — and the more we have to learn to say ‘no.’ Which makes the ability to gracefully decline jobs, dates, and opportunities one of the most important tools in our toolkit.

Like any skill, that ability grows stronger the more often you work it. With the principles we’ve covered in this piece, it will become even easier. Over time, you’ll find that saying ‘no’ isn’t the exercise in discomfort and disappointment we thought it was. It can actually become a productive (and often very fun!) conversation. We just have to reframe our conception of ‘no,’ and consciously use it to build better, deeper, more thoughtful relationships.