Some Unsolicited Advice

There is something inherently suspicious about a person who decides, without being asked, that other people might benefit from her advice.

I realize this.

Unfortunately, it has not stopped me.

You have been gracious enough to read my essays, send me notes, offer feedback, click the little heart, and generally indulge me while I have told you about my family, my work, my mother’s death, my dog, my clothes, New York, getting older, starting a business, running one, and various other subjects I apparently believed required public examination. After all that, it seemed only fair that I finally give you something useful.

So I have some advice.

Quite a lot of it, as it turns out.

For context, I am a Capricorn Sun, Virgo Rising, Libra Moon, an INFJ, and the eldest child. I realize none of these are qualifications. Taken together, however, they may explain why I have so many opinions about how things ought to be done.

And now I have a platform.

This seems dangerous.

I realize unsolicited advice is generally considered obnoxious, which has never been a particularly effective deterrent for me. Besides, most people asking for advice do not actually want it. They want confirmation that the thing they have already decided to do is an excellent idea, preferably from someone who can make it sound like wisdom.

I know this because I have been both people.

I should say that I do not consider myself a businesswoman. This is somewhat inconvenient because I spent nearly ten years running a business and now seem to spend an astonishing portion of my life on the telephone with accountants and lawyers sorting through my family’s business affairs.

I am a creative person who, through a series of decisions I apparently made voluntarily, has acquired an unreasonable amount of practical experience in things I never particularly wanted to know about. Contracts. Taxes. Ownership percentages. Insurance. Banks. Employees. Factories. Negotiations. Legal documents. The surprisingly complicated question of who owns what—and the even more complicated question of what everyone thought they owned.

I would still much rather discuss a book.

Nevertheless, there is something useful about repeatedly finding yourself in rooms you did not train to enter. Eventually you learn how the room works.

I started a company and ran it, somewhat successfully. I have made money and lost money. I have hired people, fired people, loved people, left people, negotiated contracts, dealt with illness and death, and encountered an astonishing number of people who apparently do not read the email they are replying to. So while I would hesitate to call any of this expertise, I have accumulated quite a lot of evidence.

I have learned some things.

For one thing, read the email and then answer the email.

This sounds less like advice than a description of how email works, but apparently it is advice.

I know we are supposed to have boundaries now. There are office hours, email hours, phone-free hours, deep-work hours, morning routines, evening routines and Sunday resets. People appear to spend an enormous portion of their lives preparing themselves to eventually do something.

I prefer to do the thing when the thing can be done.

If I am standing in line and an email requires a two-sentence response, I answer it. If it comes at eleven o’clock at night and I know the answer, I answer it. If it is Sunday and it will take forty seconds, I cannot imagine preserving it for Monday morning, when it will have acquired several friends.

Obviously, if an accountant sends me a spreadsheet requiring three hours and documents I do not possess, I am not completing it from the back of a taxi. I am not insane. But I have always worked for myself, so work has never been a place I go. It appears throughout the day asking to be dealt with, and I deal with it.

I find this considerably less exhausting than saving everything for later.

The same preference for making things less complicated has shaped how I deal with people.

I also believe you can never make a good deal with a bad person.

I should probably explain what I mean by “bad person,” because I am not suggesting that everyone I find difficult is morally corrupt. That would be both unfair and, given the number of people I find difficult, statistically alarming.

I mean character.

A good person can be difficult. They can be demanding, stubborn, cheap, irritating, self-interested and an absolute nightmare on a conference call. They can negotiate hard. They can want the better end of the deal. None of this particularly bothers me.

What matters is what happens when their interests and yours stop being perfectly aligned. Do they remain fair when fairness costs them something? Do they honor what they agreed to when it is no longer convenient? Do they tell you the truth when the truth weakens their position? Can they distinguish between getting a good deal and taking advantage of someone?

That is what I mean by a good person.

And by a bad person, I don’t necessarily mean a villain. Most people who make terrible people to do business with are probably quite pleasant at dinner.

I mean someone whose principles become surprisingly flexible the moment there is something to gain.

This took me longer to understand than it should have. We tend to think a good deal is made of good terms: the right price, the right percentage, the right protections, everything written down, initialed, countersigned and preferably reviewed by someone billing in six-minute increments.

All useful.

But the person on the other side of the deal is also a term.

In fact, they may be the most important one.

You can negotiate magnificent terms with someone you cannot trust and still have a terrible deal. Every ambiguity becomes an opportunity. Every unforeseen problem becomes leverage. Every agreement eventually requires another agreement explaining what everyone thought the first agreement meant.

You are constructing something on unreliable ground and congratulating yourself on the architecture.

I would rather have a slightly less favorable deal with a fair person. Perhaps the price is not exactly what I wanted. Perhaps the terms favor them a little more than I would prefer. Perhaps I even walk away knowing they did better than I did.

Fine.

A deal does not have to be perfectly equal to be good.

What matters is what happens next.

When something inevitably goes wrong—and something always goes wrong—I would rather be dealing with somebody who wants the arrangement to remain fair than somebody who has just discovered an opportunity to extract more from it.

Contracts are written for what everyone can anticipate.

Character is what you are left with when something happens that nobody anticipated.

This applies well beyond business. Before becoming terribly interested in the terms of any arrangement, look at the person sitting across from you. Not whether you like them. Not whether they are charming. Not whether you would invite them to dinner.

Can you trust them when your interests diverge?

That is a much more useful question.

You can spend months improving the terms of a deal.

You cannot negotiate someone into having character.

And while we are discussing negotiations, the person who cares less usually has more leverage.

This is unfortunate but useful information.

The person who can walk away is almost always in a stronger position than the person who absolutely needs the deal to happen. This applies to business, money, jobs, apartments, relationships and probably most things involving two human beings and a desired outcome.

The more desperately you need one particular result, the more likely you are to begin surrendering things to obtain it. You accept the price. You overlook the condition. You decide something you cared about yesterday isn’t actually that important. Eventually you have enormous skin in the game and the other person has almost none. The imbalance tends to announce itself. Once one person knows the other cannot bear to lose the deal, the job, the apartment or the relationship, the terms have a peculiar way of changing.

I don’t recommend pretending not to care. Manufactured indifference is usually transparent and always unattractive. Care enormously. Try very hard. But retain the ability to walk away.

Sometimes the strongest negotiating position is simply having somewhere else to go.

This brings me to asking for things.

Ask.

My mother was exceptionally good at this. She knew exactly what she wanted, exactly how she wanted it done, and somehow made refusing her seem slightly more awkward than simply doing it. She was gracious about the whole thing. Charming, even.

I inherited the persistence with somewhat less of the ladylike presentation.

Still, the principle works.

You would be amazed by what happens when you simply ask. People move appointments. Fees are reconsidered. Someone finds another option. A rule turns out to contain a footnote. The thing that was absolutely impossible at 10:15 becomes surprisingly manageable by lunch.

Sometimes the answer is no.

You will survive.

But ask specifically. Vague people receive vague outcomes. If you want Tuesday morning, don’t say you’re flexible next week. If you need something by Friday, say Friday. If you have a budget, say the number. If you have a standard, communicate it.

Other people cannot meet standards you have neglected to tell them about.

People occasionally confuse having standards with being difficult. They are not the same thing, although I am willing to concede there can be overlap.

Negotiate, too.

Ask what something costs. Ask what is included. Ask whether the fee can be adjusted. Ask whether there is another way to structure it. Money has the peculiar effect of making otherwise articulate adults behave as though speaking plainly has suddenly become vulgar.

The worst outcome is frequently the price you already had.

And perhaps none of it works. You don’t get the job. The person says no. The price doesn’t move. The exception isn’t made.

Fine.

You asked. You tried. You participated.

There is very little to be gained by sitting politely on the sidelines of your own life hoping somebody eventually notices what you would like and delivers it to you. This is not generally how life works. You have to enter the conversation.

Occasionally this requires making yourself slightly annoying.

I can live with that.

I also think presentation matters.

I realize this is dangerous territory for a fashion designer because it sounds as though I am about to tell you to buy a blazer.

I’m not.

I mean presentation in the broadest sense. How you dress, certainly, but also how you speak, write an email, keep your home, set a table, design a website, wrap something, enter a room. Packaging matters because packaging is part of how a message gets delivered.

My mother understood this instinctively. She could be sitting at home at nine in the morning in a silk dress, jewelry on, makeup done, drinking tea after having already sent her tenth email of the day. This was not because anyone was coming over. Often nobody was.

That was simply how she met the day.

I am considerably more casual. I wear the silk dress when I have somewhere to go. I am perfectly happy in a button down shirt or sweater, depending on the weather, for most of the intervening hours. So this is not an argument for dressing up. It isn’t even particularly about clothes.

It is about understanding that presentation is another language.

People are extremely visual. We make judgments quickly, often before we have enough information to deserve the confidence with which we make them. Malcolm Gladwell wrote an entire book, Blink, about how much can happen in these nearly instantaneous judgments—what he calls “thin-slicing.” I wish we all waited patiently for the complete body of evidence before forming an opinion of another human being.

We do not.

You can object to this, and often you should. People make terrible assumptions based on appearance. They mistake money for intelligence, polish for competence, informality for laziness, beauty for goodness and expensive things for taste. Presentation is not proof of character.

But it is still information.

Your presentation communicates something whether you intend it to or not. The question is not whether people should judge you. They will. The more interesting question is whether what you are communicating bears any resemblance to what you meant to say.

That applies to much more than a person. Walk into a home and you learn something before the owner tells you anything. Look at a company’s website. Read the first three lines of an email. Notice how somebody treats a waiter. See what they chose to put on the wall. None of these things tells you everything.

But they tell you something.

I think this is what years in fashion taught me more than anything else. Presentation does not have to be superficial because the surface can carry meaning. A beautiful book cover does not improve a bad book. But it may make you pick up the book. A beautifully plated meal does not make bad food good. But presumably the chef did not throw it at the plate from across the room for a reason.

The message and the delivery are not the same thing.

But the delivery affects whether anyone receives the message.

For almost eleven years, I told stories through clothes. I didn’t understand this quite so clearly when I started my company. Fashion was simply the mechanism closest to me.

I think I am fundamentally a storyteller.

Clothing happened to give me the materials.

Every collection had its own vocabulary: fabric, color, silhouette, proportion. Then came the photographs, the location, the short film, the styling. None of it existed separately in my mind. Everything had to work together.

I thought of a collection almost like an orchestra. You can hear the violin, certainly, but the violin is not the point. The point is what happens when it enters beside everything else at precisely the right moment.

Apparently I still think this way.

In this case, the materials are words.

And I still believe everything needs balance.

There it is. The Libra Moon. I knew she would eventually demand to be included.

I don’t mean balance in the modern wellness sense, in which one apparently works for twenty-seven minutes, drinks an electrolyte, journals, takes a walk and congratulates oneself for having boundaries.

I mean composition.

Knowing when something needs more and when it needs less. Knowing what needs to sit beside what.

A collection needs proportion. A room needs negative space. A meal needs acid. An orchestra cannot have every instrument playing at full volume for forty-five minutes.

Neither can a person.

Humor belongs beside sadness. Beauty can sit beside death. The ridiculous can happen in the middle of the profound and frequently does.

Everything has to work together.

By now you have probably gathered that I am a little fancy.

This is not breaking news.

But I have an almost equal aversion to pretension, which creates useful internal quality control. I like beautiful things. I take aesthetics seriously. I take my work seriously. I even take myself seriously, up to a point.

Then I become suspicious.

There is a point at which seriousness becomes self-importance, taste becomes performance, and refinement becomes something everyone else has to endure.

I try to stop just before that.

Learning to be direct has been harder for me. A therapist once told me that clarity is kindness, which sounded suspiciously like something one might find printed on a mug.

Unfortunately, she was right.

The more business, legal, financial and personal matters I have had to handle, the more I have learned that there is almost no substitute for saying exactly what you mean. Not approximately. Not something adjacent to it because the actual sentence might make another person uncomfortable.

The sentence.

Sometimes I have to say the same thing several times. I used to assume this meant I had failed to explain myself properly. Now I understand that occasionally the person has heard me perfectly well. They simply dislike the answer.

These are different problems.

No, I don’t want to do that.

No, I still don’t want to do that.

Yes, I understand what you’re saying.

No, that has not changed my answer.

You would be surprised how often repetition is mistaken for negotiation.

And once you have finally said the difficult thing, prepare for bargaining. You will experience tremendous relief for approximately eleven minutes. Then the counteroffer arrives.

Perhaps there is another solution. Perhaps you misunderstood. Perhaps they could change this one thing. Perhaps you could reconsider. Perhaps everyone should get on a call.

Never underestimate the human belief that another call will solve something.

This is when clarity stops being a communication skill and becomes an endurance sport.

You have to be willing to let someone be unhappy with you. They may be angry. They may think you are selfish. They may decide they don’t like you anymore. You may discover that you did not mean quite as much to them as you thought you did. Or they may be furious on Tuesday and perfectly fine by June.

Let them.

Do not change an honest answer merely because somebody else finds it inconvenient. And do not negotiate against yourself. This is how people end up living with decisions they knew they didn’t want while everyone around them assumes they are perfectly happy because, technically, they agreed to them.

I have also become considerably less interested in determining who is right.

This is not because I have become more agreeable.

I simply think many things in life have much less to do with right and wrong than we pretend.

Think of a kaleidoscope. The same pieces, turned slightly, produce an entirely different picture.

People do this constantly.

Two people can experience the same relationship, conversation, family, business arrangement or Tuesday afternoon and tell completely different stories about it. Sometimes both stories are true.

Facts still exist. If the light is red, it is red. Perspective does not make it green. But most of human life is not a traffic signal.

One person believes they were being helpful. The other felt controlled. One person believes they were giving someone space. The other felt abandoned. One person thinks an arrangement is generous. The other thinks it is insulting.

Both may be describing the same thing accurately from where they are standing.

It is tempting to believe that if you explain yourself with sufficient precision, the other person will eventually see exactly what you see.

Sometimes they won’t.

They’re standing somewhere else.

I don’t need another person to agree with my version for my version to remain true. And I don’t have to adopt theirs to understand how they arrived at it.

Turn the tube.

The picture changes.

This is particularly useful when dealing with situations you have somehow allowed to become intolerable.

If you find yourself in one, ask what you have been willing to tolerate that led you there.

This does not apply to every terrible thing that happens. Terrible things arrive without invitation all the time. I know this better than I would like to.

But other situations do not arrive.

They accumulate.

Something bothers you. You let it go. Something else happens, but there is a perfectly reasonable explanation. Then another reasonable explanation appears. Eventually you are standing in circumstances you would never have knowingly chosen, wondering how on earth you got there.

Usually, gradually.

Ask yourself what the first thing was that you accepted that you should not have accepted. Ask what you knew before you were willing to admit that you knew it.

This is not an especially enjoyable exercise. It is, however, more useful than deciding everyone else is an idiot.

What you tolerate once may be an exception. What you tolerate repeatedly becomes an arrangement.

And once it becomes an arrangement, changing it will generally upset whoever was benefiting from the arrangement.

They will manage.

Everything passes.

This has become considerably clearer to me recently. Embarrassment passes. Anger passes. Rejection passes. Success passes. Terrible periods pass. Wonderful periods pass too, which is the less marketable half of this philosophy.

People recover from disappointment. They adjust. They rearrange their lives.

So do you.

Sometimes clarity costs you the relationship. That is painful. But agreeing to something you do not want in order to preserve a relationship is a peculiar way of preserving anything.

People leave. Things end. You continue.

I don’t find this pessimistic. I find it enormously freeing. Very little deserves the permanence we assign to it while it is happening.

I also no longer believe that things “figure themselves out.”

People say this constantly: Don’t worry. It will all work itself out.

No, it won’t.

You will figure it out.

There is an important difference.

Life will certainly continue without your participation. Time is extremely efficient that way. But if you don’t make decisions about where you are going, other forces will happily make them for you.

Put a boat in the water and do absolutely nothing. The boat will still go somewhere. The current will move it. The wind will move it. Another boat may move it. Eventually you will be somewhere entirely different from where you started.

This should not be confused with navigation.

If you would like to go somewhere in particular, eventually you have to drive the boat.

There are seasons when you cannot. You are exhausted. You are grieving. You are sick. You are lost. You have no idea where you want to go and would prefer everyone stop asking.

Fine.

Take your hands off the wheel.

Rest is not surrender. Sometimes doing nothing is exactly what needs to be done.

But the water is still moving.

I don’t think changing your life usually requires changing your life. Most of the time it is much less theatrical than that. You make a decision, and then another one, and six months later you discover that you have been moving in a direction. This works equally well in directions you did not intend to go.

Very few people wake up one morning and deliberately construct a life they dislike. They make a series of perfectly defensible choices, tolerate a few things longer than they should, postpone a few others, and eventually look around with some surprise.

This is why I am suspicious of transformation. It is too dramatic a word for what usually happens. Most change is almost insultingly ordinary while it is occurring. You answer something instead of avoiding it. You stop agreeing to something. You spend the money or don’t spend it. You leave earlier. You stay longer. You make one choice differently than you made it before. Nothing particularly cinematic happens.

Then, eventually, you are somewhere else.

This is also why I think you have to keep going.

There will be days when life feels completely insurmountable. There will be conversations you don’t want to have, rooms you don’t want to walk into, decisions you don’t feel qualified to make and things you are certain everyone else somehow knows how to do.

Do them anyway.

The first time may be awful. The fifth time will probably be less awful. By the twentieth, you may wonder why it once frightened you so much.

I don’t think the goal is to arrange a life in which nothing makes you anxious, uncomfortable or afraid. You would have to make your life extraordinarily small to accomplish that.

I would rather become better at being uncomfortable.

Life is hard.

Actually, life can be brutal.

People die. Relationships end. Businesses fail. Bodies disappoint us. Money disappears. Plans collapse. People behave badly. Occasionally several of these things happen at once, which seems unnecessary.

And then life can be wonderful.

Someone makes you laugh when you thought you had forgotten how. Something you were certain would never work does. You fall in love with a person, a place, a dog, an idea. You have a perfectly ordinary Tuesday and realize halfway through it that you are happy.

Neither condition lasts.

This may be the most comforting thing I know.

The terrible passes.

Unfortunately, so does the wonderful.

The sooner you stop expecting life to remain permanently in one condition, the easier I think it becomes to live. Enjoy what is good while it is here. When it is terrible, do the next thing you can do. When you don’t know what to do, wait until you do.

Then move.

Life is not supposed to be easy. I am increasingly suspicious of anyone selling a method suggesting otherwise.

I should probably say that I don’t think any of this is particularly easy to do. Knowing that you should say no does not make saying no pleasant. Understanding that something will pass does not make it hurt less while it is happening. Knowing you should walk away and actually walking away remain, rather inconveniently, two different things.

I am also not especially interested in the kind of self-help that promises a new life if you wake up earlier, think differently or purchase the accompanying workbook. But I do believe there are observations about living that, once somebody says them to you, can change the way you see a situation.

Sometimes another person’s experience gives you language for something you already knew but hadn’t quite understood. Sometimes one sentence saves you several years of learning it the expensive way.

That seems useful to me.

So if one or two things here stay with you, take them. Leave the rest.

Perhaps that is the only advice I have.

Answer the email. Ask the question. Negotiate the price. Say what you mean. Have standards. Pay attention to the packaging. Choose the person, not merely the terms. Retain the ability to walk away. Accept that somebody else may see the same thing entirely differently. Stop tolerating what you already know you cannot tolerate. Let someone be disappointed in you. Risk being disliked. Walk into the room. Drive the boat.

Try.

You may do all of this and still not get what you want.

In fact, at some point, you definitely won’t.

That is not evidence that you shouldn’t have tried.

I no longer believe life reliably rewards the wisest decision, the nicest person, the hardest worker or the person who followed all the instructions. I have seen far too much evidence to the contrary.

But I do believe you have to participate.

You have to make choices while knowing they may be wrong. Ask for things you may not get. Say no without knowing what the no will cost you. Leave bad arrangements before somebody can guarantee that a better one is waiting. Keep moving, even when the movement is embarrassingly small.

Then live with what happens.

Fortunately, that will pass too.

It may not figure itself out.

But you will.