Freelancer’s Survival Guide: The Benefits of Hindsight

Freelancer's Survival Guide On Writing


Artwork donated by Pati Nagle.

The Freelancer’s Survival Guide: The Benefits of Hindsight

Kristine Kathryn Rusch

I don’t know if we get wiser as we get older, but we certainly gain a lot more experience.  The experience comes in handy, if we chose to use it.  And sometimes that experience is just there, a part of our personal history and nothing more.

I had a discussion with someone this recently about hindsight.  We both discussed our fathers, both of whom discouraged us from our first marriages.  The person I was talking to is going through a divorce right now.  I went through mine 24 years ago.

We both agreed, in the course of our conversation, that our fathers had been right. We also agreed that if we had looked at those relationships now—from the outside (with someone not us) and with the benefit of another couple decades of living—we would see the upcoming problems as well.

Relationships follow patterns, and people often get attracted, particularly early on, to someone who might give us an opportunity to heal problems that currently exist in our own lives.  Watching other people’s relationships have given me insights into my own.  But that all comes from experience (and an annoying tendency toward nosiness).

The conversation with my friend wasn’t a bitter one though.  In fact, we both laughed about our poor fathers’ inability to stop us, and we both expressed some empathy for our fathers in that situation.  Because as clearly as our fathers could see the situation, their experience didn’t extend to preventing it.

Then, of course, both of us contemplated what might have happened had we listened to our fathers. If I hadn’t married the first time, I would probably never have met my current husband.  If I hadn’t met Dean, I certainly wouldn’t be typing this now.

As I’ve said before, I don’t regret that first marriage, despite the pain and anguish it caused me and my ex.  Not only do I (we, I hope) have some good memories, but that relationship was a critical one in forming both of us.  Fascinatingly to me is this:  Had my ex and I stayed together, his children would never have been born.  Had we done things “right,” he would have lost the family he has now, and probably not had a different one in its place.  I never wanted children, which we discussed at the beginning.  My ex, at nineteen, figured (without telling me) I’d change my mind.

I never did.

Most of us use hindsight the way I did here, to explore the various possibilities of our lives, the paths not taken.  I actually looked at that very topic in a story I just published in Analog, called “Red Letter Day.” The idea being if you could write a letter to your younger self, helping that person either change something in their life or not, what would you write? Would you write at all? (Still haven’t entirely answered that one for me.)

But we can use hindsight for more than what-if exploration.  We can use hindsight as we build our businesses.  In fact, I believe hindsight is an essential tool of business building.

In my post on failure, I wrote, “Failure is something we need to practice.  Handled well, failure leads to success.  In fact, I know of no long-term successful business person who lacks a failure in her background.”  Later in that post, I wrote that I believe that failures handled well are more properly termed setbacks.  Of course, I wrote three posts on the topic of setbacks as well.

What changes a failure to a setback? Attitude.  I know a number of people, several of them men, who have not remarried after their divorces.  Most of those men never even dated again.  They were so rocked by the failure of their marriages that they simply could not conceive of another relationship at all.  They weren’t willing to try again.

Sometimes this attitude is healthy.  It comes from suffering physical pain.  It’s hardwired in.  When we get hurt badly, we don’t want to repeat the behavior that caused us that pain.  This makes sense when it comes to touching a hot stovetop with your bare hand—you’re not going to do that again if you can at all help it—but makes a lot less sense when applied to everything in life.

If we avoided everything that hurt us, emotionally and physically, over the years, we’d eventually stop doing anything.  I’ve turned my ankle crossing a room without tripping on anything; does that mean I shouldn’t walk again?

Back in the failure post, I used the analogy of the child learning to walk. Toddlers don’t give up.  They want to move on their own too much to stop, even though they fall constantly and often hurt themselves.

But that’s a simple analogy.  I don’t think (don’t remember, honestly, and don’t really know) whether or not toddlers analyze what made them fall.  I suspect toddlers just get right back up and try again without any real thought except some version of I’m going to conquer this thing; everyone else I know has.

That bullheadedness serves us well in many areas of life. Sometimes you need to get right back on the horse, the bike, whatever cliché you prefer.

And sometimes you need to analyze what went wrong.  You need to use hindsight.

Because I have a driving desire not to ever make the same mistake twice, I get really angry at myself when I do make a single mistake over and over again.  I don’t quit whatever it is I’m doing—I’m closer to that bullheaded toddler than I let on in public—but I do rethink it, and sometimes I take a vacation from it.

Case in point: Business.  Business, unlike writing, is something I learned as an adult.  I’m a very organic writer.  I read, gather information, and eventually apply it.  I can teach what I’ve learned—somewhat.  But as I recently explained to a group of professional writers who had all come to study with me, if you delve too deeply into my ability to express my knowledge about writing, you’ll learn that my ability to describe what I know is pretty shallow. At some point, I just shake my head and say, “Look, just do it.  If you can’t do it then, we’ll see what else we can figure out.”  Not because I’m frustrated with the student, but because my own learning process in that area is so subconscious that I can’t even articulate how I know what I know.  And sometimes expressing what I know is equally hard.

On the other hand, I learned business in the school of hard knocks.  And when I say hard knocks, I mean the kind that make little cartoon birdies and stars revolve around your head for years.  I can point out each wound and scar, each dent to my thick skull, and every single slight that every happened, my fault or not.

Why am I not bitter?  Sometimes I am.  I occasionally indulge in the pity party or the nasty analysis of someone who has hurt me years ago.  But mostly, I learned relatively young that looking backwards and wallowing in regret does me no good whatsoever.

Life moves forward whether we want it to or not.  Our choice is whether or not to move with it or to give situations the permission to batter us around.

Hindsight is the tool that allows us to move forward.  It is also the tool that allows us to go near a stove again.  We assess what went wrong, and then we see if it’s even possible to move forward again without repeating the same mistake.

Once you put your hand on a hot stovetop, you realize that you have to approach that stove with caution.  A toddler might stay away from the stove entirely, since a toddler can’t see the top, and judges the entire thing harmful and can’t yet understand a stove’s benefits.

But an adult realizes that there are many ways to approach that stovetop, most of which will not hurt, if you’re careful.  One thing most of us do, however, is keep our bare hands away from any part of the stove that’s on.  Most of us never put our hands on that top without looking at it first.

Simple caution, based on experience.  It allows us to have a useful, if dangerous, item in our home.

But let’s move hindsight away from the realm of the physical into the realm of the mental.  Pain can be emotional.  The emotion comes from severe stress and trauma.

I’ve owned many businesses, and I’ve failed at a lot of them.  I’ve approached each one with the idea that I won’t make those same mistakes again.  Often, I decided not to go into the same kind of business again.

When Dean decided to open a collectibles store as a hobby, I wanted nothing to do with it.  I had worked retail from the age of twenty forward, and my ex and I owned a frame shop and art gallery that was a retail shop.

I hated most of the aspects of owning a store.  I hated the hours.  I hated the stuff.  I hated the cash outlay required to get inventory, to rent (or buy) a building, and most of all, I hated waiting for customers to come in.

But Dean had owned several shops, and had loved them.  I was not about to stop him from doing something he loved.  So I helped him plan, using the mistakes my ex and I had made in the past, combining those mistakes with the ones Dean made in his early stores.

That planning, and all of that hindsight, allowed us to build a successful business.  I didn’t ever stand behind the cash register, but I was part owner.  Dean and I made the major decisions together.

Our experience paid off.  Dean’s expertise in collectibles made the store a destination stop within its first year.  The inventory came from Dean’s collections, and his judicious purchases of other people’s collections.

Because Dean knows himself quite well, he also realized that the joy in any project for him is building that project.  (That’s why he became an architect.)  He literally built this business from scratch, making a deal with an owner of a strip mall that we would pay to fix up a dilapidated space inside that mall in exchange for three years of rent.

The nice thing about that rent deal and the previously owned inventory is that together, they gave us the opportunity to walk away from the business if it didn’t work.  We had three years of free rent, so we had three years to see if the business could sustain itself.  We had more than a year’s worth of inventory, so we had relatively few start-up costs.

The business became so successful so quickly (which we did not expect) that Dean realized he was going to have to put more time into it than he had planned. That realization too came from experience.  He had done this before, and he knew how to grow a business.  He did not want to become a collectibles mogul. This was supposed to be his hobby, not his life.

Once he made that realization, he sold the business—for a profit—six months after Oregon, already ahead of the curve, had sunk into this deep recession.  The new owner, who had worked at the business from the start, maintained it, and it continues to grow even now, doing extremely well in this tough economic climate.

Every single plan we made about that new business came from hindsight.  We knew, first of all, that Dean needs to build things.  He always has something going on besides his writing.  Before he wrote, he had two or three new things happening as well.  He must create on a variety of levels, and it’s impossible to hold him back—although he’s great at analysis, and able to figure quickly if a new project is the right project for him.

That ability to figure out if a new project is right also comes from experience.  In our lifetime together, he’s started projects only to abandon them within the week as it became clear that he wasn’t suited for them. Time has taught us to evaluate first, sink money in later.

Experience taught us to do the financial plan up front.  We’d both started businesses by the seat of our pants, with just a vague idea that it would work out.  Once or twice it did, but mostly it failed.

We also learned that we needed to spend as little on start-up as possible because we were taking no outside investors.  We needed to be able to walk away from this business.  Because of our years of experience we knew that the economy was headed downward (long before the “smart guys” in Washington had it figured out), and we had to make the business as recession-proof as possible.  We’d both started businesses in a recession, and we lost Pulphouse Publishing in part because of our response to the recession of 1992.  So we knew how dangerous the overall economic climate could be to a business.

We planned for that.

We also knew the price we needed if we decided to sell the business, and we knew it up front.  Mostly, we expected to shut it down if it didn’t work. The fact that we found a buyer with little effort had more to do with Dean’s planning abilities than with me, but he doesn’t like building things only to take them apart.  So he worked hard to keep potential buyers interested, even while he started the business up.

All of this planning was extremely different from the planning we had done in our early businesses.  Those, as I said, were done without enough planning at all.  In fact, as I mentioned in the business plan post [link], I didn’t understand why places like the Small Business Administration wanted a business plan.  How could we know how the business would operate when we hadn’t operated a business?

I recently watched a business go through the same by-the-seat-of-their-pants start-up, and I haven’t even talked to or met the owners.  I recognize the signs from experience alone.

Down the hill from our house, a lovely Italian restaurant went out of business but not because of financial mismanagement.  The place was wildly successful.  Instead, it closed because of what I think of as a weird Oregon Coast phenomenon.  The owners got sick of tourists.

We went to this restaurant a lot, and in hindsight, the signs of the closure were obvious.  It started when the owner decided that locals could make reservations, but tourists could not. Then it migrated to little signs on the table, telling people to control their children and not to use their cell phones.  Then the hours got strange—staying open on Monday and Tuesday (traditionally days on the Oregon Coast when business are closed because there are no tourists) and closing on Sunday.  In their last year, the owners closed for the summer (the high season) and reopened in the winter (when the town is empty).  The reopening didn’t last.  In fact, the restaurant closed for good during, of all things, spring break.  The owners loved to cook. They loved to cook for people they liked. They hated dealing with rudeness, demands, and all the other things that come with owning a restaurant.

They had owned their building, and it sat empty for two years, waiting for a buyer or for someone to rent it.

This spring, someone rented it.

Because the restaurant is so close to us, we watched the newcomers build it.  A small sign went up immediately, announcing the future home of the new restaurant.  The front door sat open during the business day, as the new owner painted and did a slight remodel. The official sign went up in late May and with it, an announcement on the changeable sign below, that the restaurant would open on June 25.

Well, I could see the interior of that place, and it was clear to me that they would have to push to hit their June 25 deadline.  On June 20, the furniture got delivered.  On June 24, the sign changed to a July 2 opening.  Fourth of July is the biggest weekend in our little tourist town, so it became clear that these new restaurateurs wanted to take advantage of that.

But both Dean and I have worked in restaurant start-ups, and a menu, a good chef, and a well-designed interior do not a restaurant make. Every single successful restaurant that we’ve worked at—and that Dean has managed—has given itself a month to work out the kinks.  Mostly, the restaurant holds practice nights with the newly hired wait staff, without opening the restaurant at all.  One restaurant in Superior, Wisconsin, when I was a teenager invited the relatives of every single person on the staff to come into the restaurant and eat free for Thursday, Friday, and Saturday night.  That restaurant did so for two weeks.

By the time it opened, the staff knew the menu, knew the quirks of the kitchen, had made (and corrected) dozens of errors, learned where everything is kept, and learned how to pace themselves through a restaurant slammed with customers.

(Our local six-plex movie theater did the same thing, by the way, just to get the bugs out of their system.)

Dean worked varieties of the same practice session.  Every restaurant that does this opens to acclaim, if not for the food, at least for the service.

On July 1, the restaurant below announced a July 5 opening date.

On July 4, the opening date was gone.

On July 17, the place held a stealth opening.  They’d lost an entire month of revenue from their business plan (if indeed they had one), and they have so far gotten no word of mouth throughout the community.  The stealth opening allowed them to practice a little, but they probably lost customers who expected a more polished staff/restaurant.

I hope they’ll survive, but their cold opening probably made things harder than they needed to be. And the cold opening is a clear sign of inexperience.

So how do you make hindsight work for you?

1. Do a fearless inventory of what went wrong in your previous business(es).  Make a list and be honest.  If you’re not honest, there’s no point.  If you did something wrong, or several somethings wrong, admit them.  You need to understand where all of the mistakes are, not just some of them.

2. Evaluate whether the mistakes came from a) the economy; b) your response to the economy; c) your inexperience or d) your personality.  If the mistakes came from the economy, then you better make sure you know how to weather the same economic climate.  If they came from your response to the economy, then you better learn how to be more flexible in response to a crisis.

If the mistakes came from your inexperience, don’t get overconfident.  Just because you have experience now doesn’t mean you’re all wise.  Plan to make more errors.

If the mistakes came from your personality, you better find a way to negate that part of you that has the tendency to do things wrong for the type of business you’re opening.  I’m great at publishing and editing, but I’ll never edit again.  I’m good at it, but not suited to it.  No amount of “change” will make me and editing suit.  I might be able to do a small project or two, but I won’t make a career out of it—not without a personality transplant.  Been there, done that, spent enough to buy a factory’s worth of t-shirts.

If the mistakes came from your personality, you might need to hire someone to take that part of your personality out of play.  I could own a publishing company (in partnership with Dean) again, if I don’t edit.  But I would have to remain hands-off with the new editor.  I would have to trust that person—which is a tall order. As I said, I’m very good at editing, and I’d see mistakes right off.  I’d probably drive that person out of the business if I wasn’t careful.

Hiring a person to do the part of the job you’re not suited for has all the pitfalls of hiring an employee for other aspects of your life.  See the employee sections of the guide.

If your previous business failed due to your personality, then you might want to reconsider stepping back into that same kind of business at all.  Sometimes it’s better to say that you don’t suit than it is to keep pounding your head against the same brick wall.

3.  Use other people’s hindsight.  Ask them about the mistakes they made in the same type of business.  Do this even if you’ve owned a business before.  You’ll learn something, guaranteed.

However, make sure you listen to their advice.  At least three start-up publishers interviewed me and Dean about what went wrong at Pulphouse Publishing.  We were very honest with them, told them about various warning signs, and told them to call us if things got dicey.

All three of those start-ups failed, one spectacularly.  All three of them followed the exact same path that Pulphouse followed, and all three responded to the problems the same way we did—which is to say, the wrong way.

They were forewarned.  Of course, they took no notes during our meeting, never contacted us when things got dicey, and only one remembered our advice at all.  He later admitted to us that he was in the hospital (the failure caused a physical collapse that put him in the hospital for weeks) and he kept hearing our voices, telling him what exactly would go wrong if he didn’t take our advice.  He says we haunted him, and he apologized for not listening.

He didn’t owe us an apology.  He owed himself one.

5. Let hindsight help you in all aspects of your business.  Because I know how a failing business behaves, I often will not work with a business that is exhibiting the symptoms of a business on the edge.  Because we had a publishing house collapse, I particularly know the signs of that, so I won’t approach a company that even whispers of trouble.  The trouble is often obvious to those of us who have been through something similar years in advance.

In fact, when Dean and I talked with one of those start-ups all those years ago, the owner told us in the middle of the meal he was buying us that he “would never ever make such dumb mistakes.”  We immediately decided never to work with him—not because he insulted us, but because his ego was so large that he believed he was immune to our stupidity.

He compounded our stupidity, and his failure was so spectacular that people within publishing still discuss it as an example of what not to do when running a business.

6.  Remember the most important lesson of hindsight: You are fallible. Sorry, kiddo.  You’ll make mistakes just like the rest of us.  In fact, you’ll  make mistakes every single time you start a new business.  You’ll make mistakes after owning that business for ten years, fifteen, twenty.   Face it: You’ll make mistakes.

Now longtime readers will understand where I get my mantra.  The key is to avoid making the same mistake twice.  You’ll always make new mistakes.  Be creative about them.  Make new mistakes in the pursuit of the perfect, mistake-free business.  Then learn from those new mistakes.

That’s what hindsight is for.  Toss out the regrets and the “I wish I hads.”  Stop fantasizing about going back in time and fixing things.

Move forward with the right attitude—after you’ve fearlessly looked backwards, of course.

“Freelancer Writer’s Survival Guide: “Hindsight” copyright 2010 by Kristine Kathryn Rusch.

6 thoughts on “Freelancer’s Survival Guide: The Benefits of Hindsight

  1. Kris,
    Thanks for this. Unlike many toddlers, I find mistakes humiliating. I am figuring out how to learn from mistakes and laugh, so this is a practical guide on how to do that.

    I also love Cindie’s comment about burning herself in the fire after the stove!

    1. You might want to figure out where you learned that mistakes are humiliating, Melissa. Often once you know that piece of information, you know when it actually applies and when it doesn’t (which is most of the time). Good luck with it!

  2. Heard this line years ago, and it is so true…

    “Life gives the test first, and the lesson later.”

  3. Oh, I needed this. I wrote out your questions and my answers. While a bit depressing, it was illuminating. I think my hindsight is a bit … mentally challenged. To use your stove analogy, I get burned by the stove and then just avoid anything metal but still stick my hand in a campfire. I feel like I make the same mistakes but in new and novel ways. In business and life. I’m hoping recognizing this is the first step toward change. Now to start thinking about what the real mistakes are, not just the ones my mind connects. In other words, time to figure out what about the stove actually burned my hand!

    1. Great comment, Cindie. Glad it helped. I sure understand how that can be. I untangled some of those strange connections myself. Good luck with it!

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