Everyone wants you to have boundaries until the boundary applies to them.
Boundaries are popular in theory.
People want you to have the same boundaries that they do, or boundaries that don’t inconvenience them in any way.
Unfortunately, that’s not how a boundary works – boundaries are all about measured disappointment.
These are the lines where you decide “I will do what I can to please you, up until this point, at which I accept that you’ll be unhappy”.
If you can’t stand to see the other person unhappy, it isn’t a boundary – that’s called being a people-pleaser and not many people-pleasers appear to be loving their setup.

What Does Disappointment Look Like?
Boundaries come into all facets of life, particularly when you’re interacting with other people and particularly when money or fun is involved.
These might include:
·      Not scheduling a work meeting for the weekend
·      Not replying to work emails after 6pm
·      Not taking your work computer with you on your honeymoon
·      Not laughing at a sexist joke
·      Having a few drinks but refusing to get drunk
·      Declining some extended family events
·      Not kissing the person you met for a date
·      Turning down an overseas wedding
·      Not having children when your parents/in-laws would like you to

In each of these, there’s someone disappointed by your choice.
That person can use several tricks to change your behaviour – guilt, obligation, fun, fear of alienation, shame, a promotion, a raise, etc.
Sometimes they make a compelling case.
Sometimes you’re caught off-guard by their sudden insistence; people will make you feel weird for not going along as they hope you will.
Here’s the catch – you can either disappoint them, or disappoint yourself.
That’s why boundaries are about managing disappointment – choosing who to disappoint, where the deal might change, and measuring which options are preferrable.

I admire (and learn from) people who handle these boundaries well.
They often use a counter-offer to try and accommodate the request:
·      “I can have two beers but that’s it”
·      “I can’t make the wedding but I’m sending a great gift”
·      “We can swing by for an hour on our way to our other commitment”
·      “I can’t talk now but I’ll send you a quick update in a few hours”

These might not be accepted, but at least they’re clever compromises.
And some scenarios don’t have middle grounds, and that’s ok.

Is This A Winnable Situation?
A great clarifying question is “Is this a once-off, or will this set a precedent?”
Some tasks are bottomless, they can’t be “completed” as such.
By saying yes to a request, you tell people that they can consistently expect this from you in the future.
If you answered work emails at 10:30pm last week, why would they think you’d be uncomfortable with it this week?
In some work cultures, there is no way of finishing the job – you will be allocated more and more, especially if you’re a fast worker.
As they say, “The prize for the pie-eating contest is more pie”.
Your agreeable nature will earn you more work, not necessarily more compensation or appreciation.
If there’s no way of being “good enough”, then it’s time to set a boundary or find a new situation.
This applies to families and friends too.
If your efforts are constantly seen as inadequate, it might be time for some tactical disappointment.

Tactical Disappointment
There are different types of disappointment:
“Sorry I’m not what you thought I would be” is different to “I’m sorry that I’m not what I thought I would be”,
and the latter stings for a lot longer.
If someone thinks you’re going to work miracles, and you don’t or can’t, that’s not necessarily an obligation.
Their hopes were high, perhaps without good reason, it’s not your job to meet those standards.

There’s also a difference between your reputation for output and your reputation for ethics.
People talk about how important your reputation is, but these are different types of reputation.
Not meeting a deadline is not the same as doing something illegal or immoral – and it’s your reputation for ethics that haunts you.
I would much rather hear “Isaac’s report wasn’t as detailed as we’d have liked, and he didn’t cancel his weekend plans to rectify it” than “Isaac lied to us and acted dishonestly”.
A flawless reputation for output is not nearly as important for a flawless reputation for ethics.
You can have projects not work out without it affecting your entire career.

Objections vs Complaints
In the sales world, a complaint and an objection are slightly different.
A complaint is a grizzle or a grumble, where someone wishes things were different or laments that they can’t have everything the way they wanted.
An objection is a roadblock or a showstopper; we can’t proceed without changing this.
So when you sense that someone is unhappy, you’ll want to deduce “is this an objection, or just a complaint?”
In other words, do they not like something or do we want/need to change something?

The reason why I mention this is that the hardest part of tactical disappointment is sitting still while someone
complains at you or complains about you.
e.g. your parents want you to invite some of their obscure old friends to your wedding, and you don’t want them there.
That’s going to annoy your parents, who will complain to you and probably complain about you to your siblings and their friends.
That doesn’t mean you’re wrong or that you should cave, it means you accept that they’ll complain and you go ahead with a wedding list of people you genuinely like.

Or if you’re an artist who takes commissions, you might set your price as “Starting at $1,300”.
There are guaranteed to be people who love your work who can’t/won’t pay that.
Some of those people will be lovely, and some won’t.
Tactical disappointment means you’ve chosen to accept that some people will complain about your prices.
Their complaints do not place you under an obligation.
Their opinion is not a fact.
You could talk to some of the lovely people and come up with a creative solution that facilitates a deal, but that’s at your discretion.

Sometimes people don’t want to spend a lot of money, and sometimes there’s a serious limit.
For my clients who work in government departments or institutions, they might only be able to say yes to deals under a certain amount; $9,999 is do-able and $10,001 isn’t.
For my clients who have extensive family wealth, they want to feel like they’re getting a fair deal, so there’s no actual financial cap but trust is essential.
The former benefits from a discount and some contract manoeuvring, the latter benefits by demonstrating your thought process and your integrity.

“That’s great Isaac, but what about when contracts are involved? What about when there are expectations and money on the line?”
A principle isn’t a principle until it costs you money, and I’m happy to tell you that boundaries and tactical disappointment has cost me money.
My suggestion is to have the option of conceding defeat.
That means returning money to the customer, or offering a discount.
The work has crossed a boundary, so it’s time to end it and find a suitable compromise.
I’ve had projects that I’ve walked away from 25% of the way through, apologising and declining to send any sort of invoice.
Money well spent!
Every time, I’ve never regretted the move, and have forgone cash in exchange for getting back my time, my energy, my enthusiasm and my reputation.
I’ve then been able to use that time, energy and enthusiasm to say “yes” to other work, which rapidly replaces the money I’d left on the table.

“Yeah well that’s all good for you, you’re not dependent on that money!”
Yes, and this is by design.
If you can’t afford to say “no” in a project, you won’t be able to maintain a boundary.
My way around this problem was to not spend any of my freelance income, keeping it until I had a big buffer.
That buffer creates freedom, the knowledge that your living expenses are sorted for the next six months.
People can’t bully you into breaking your boundaries with the threat of non-payment.
And while it’s best to avoid working with bullies in the first place, the second-best option is to leave when they reveal themselves.
You’ll be stunned at how much this surprises customers, who believe that money gives them magic powers over you.
For this reason, the best thing you can buy with your freelance money is cash in the bank.
It beats expensive laptops, fancy branding, a big Christmas party or a nice office space.
If you have all the trappings but your customers have you over a barrel, you and your team are likely about to be miserable.

In reality, this might require you to grow your business slower, so that you’re not at the mercy of major customers.
Not many people are out here promoting this strategy, but it saves you a major headache from becoming dependent on a few people and their increasing demands.

What You Control And What You Don’t
Not everything is within your control, and crucially one of those things is other people’s opinions.
This is one of the best lessons from the book The Courage To Be Disliked, which says that other people’s opinions are none of your business.
You can’t control these opinions, so why be at their mercy?
You own your actions, they own their opinions.
And while you can try to sway or influence those opinions, you don’t get the final say and you’re not dealing with logic.

You’re probably thinking “Well I can probably sway them if I work hard”.
Think of someone you don’t like; can they force you to like them?
Exactly.
They can try, but you’re allowed to hold whatever opinion you like.
And this is important for a boundary – if you can’t accept someone having a low opinion of you, then they have you over a barrel.

Sometimes it seems lucrative to go against your instincts so that others might like you, which often gets rewarded in the short term.
Ultimately, you have to live with yourself, and they don’t.
They might like you at work or in that group, but if you don’t like yourself then they payoff will be unsatisfying.

Other people’s opinions are useful in identifying your strengths and weaknesses, but they are skewed forms of data.
There are people who hate my favourite movies, favourite books and favourite foods, and there comes a point where you have to say “Ok, I respect your opinion and I respect you as a person, I also think you’re dead wrong and I’m probably not going to ask you for any more recommendations”.
You can’t please some people, and trying to is futile.
e.g. if they don’t like your past work, and they don’t like the work that inspires you, what chance do you have of pleasing them without massively compromising?
A good alternative is to go hunting for other groups, people who are more likely to value you as a person and value your work.
There are always more clients, more employers, more peers, more communities.
Swapping groups feels costly, but it might be better than trying to please the unpleasable?

The Happiness Equation
Tim Urban describes the formula for happiness as:

Happiness = Reality – Expectations

You’ll probably have experienced this for yourself:
If you think a new movie will be amazing and it’s just ok, you leave feeling deflated.
If you get dragged to a movie and it’s actually ok, you leave feeling pretty good!

What’s interesting is that you can control both variables – the reality and the expectations.
I think western work culture encourages you to put lots of energy into controlling the reality – making sure that what you make is brilliant and pleasing – but the other variable is controlling what people expect of you.
By removing some deliverables or reducing what you promise, you give yourself more chances to “under-promise and over-deliver”.
Under-promise and over-deliver is great in theory, but gets thrown in the bin by salespeople the moment they feel like they’re in a competitive bidding environment.
That means you’ll need to get good at weighing up the benefits of making certain promises and setting expectations; too low and you might not get the work, too high and you might regret getting the work (as will the client).

One way of doing this is to make progress in secret – not telling people about the skills you’re developing until they’re of a decent standard and you know how you want to use them.
It’s hard to not mention them at times, but this prevents people from assuming that you’ll be able to fulfill their every request, which are often far too lofty and ill-informed.

Boundaries are costly.
They cost you work, money and being liked.
Not having boundaries is even more costly – compromising your reputation, your mental health and your work/life balance.
You can choose to embrace the costliness of boundaries by filtering who you spend time with, what promises you make and how much you need to avoid disappointing others.
With planning and reflection, you can create a system that isn’t dependent on everyone liking you or your decisions, like having multiple friendship groups, multiple sources of income, and good people who can be a sounding board when you’re conflicted.
Once you know what your boundaries are, you’re able to be as generous as you like.
You can make offers and accommodate people, knowing that this generosity and flexibility won’t come back to haunt you, and won’t be exploited by those around you.
And whenever you find yourself feeling uncomfortable, ask yourself “what might this be telling me about a future boundary?”.