Stories of business failure
June 19, 2019 5:59 PM   Subscribe

Like many people, I often daydream about quitting my boring office job and starting my own business. Also like many people, I don't ever actually do anything about it. I've realized that one of the biggest reasons why (aside from, you know, lack of cash lol) is because I'd be terrified of my business failing.

All the entrepreneurial advice you see is "don't be afraid to fail", but that's easier said than done. I'm almost 40, married with one kid and another on the way. My family needs things like health insurance, food, and a place to live that's not my mother-in-law's guest bedroom. But obviously, people do start businesses that fail, and they don't end up living in a cardboard box. So it seems like it's possible to fail at owning a business without actually losing everything. As a way of confronting my excuses, I'd like to hear/read those people's stories.

I want stories with a structure like:

1. Idealistic cube monkey gets an idea for a business.
2. They open the business.
3. It turns out the idea isn't very profitable.
4. They decide to close the business.
5. They go back to a boring cube monkey job.

Of these, Act 5 is the one I'm most interested in. Not the failure, but the recovery: the landing on the feet. I'm not as interested in the first two acts; there are millions of startup stories out there. Preferably things I could read online (i.e., while I'm killing time at my boring office job ;) ).
posted by kevinbelt to Work & Money (14 answers total) 14 users marked this as a favorite
 
Number 3 can be something different from, or in addition to, lack of profitability. I ended up wanting to murder my massage business partner (no hyperbole). This was someone I'd known for many years and got along fine with, until we started a business together. Then our relationship plummeted like the stock market in '08. This is not uncommon, from what I read/hear.

He was a tyrant who would do things like put art on the walls that I'd expressly said I hated (and wasn't appropriate for a massage room), plus a hanging system that didn't allow me to take them down. We had already agreed to hang anatomy posters, I had personally already ordered and paid for them, and then he went behind my back and did that. I came in for a session one day only to find NEON PINK AND ORANGE FLOWERS plastered all over the walls. You really haven't lived until you have tried to give someone a soothing massage while seething with rage. This is one of approximately 9,875 shitty things he did. We no longer speak.

Number 3 can also be "Business was profitable, but ate up all my time and I had no time to spend with my family, so I went back to 9-5, and then really appreciated my free time like I never had before".
posted by nirblegee at 8:29 PM on June 19, 2019 [4 favorites]


A Restaurant Ruined My Life
posted by stray at 8:40 PM on June 19, 2019 [1 favorite]


Long story short: I was having trouble finding work so in 2014 I bought an existing business with the idea of being my own boss. I regretted it almost immediately. I sold the store within a year at a huge loss. I went back to school in 2016 and landed a dream job a year ago.
posted by mpark at 10:43 PM on June 19, 2019 [3 favorites]


I have something along those lines, maybe this will be helpful.

In 2000, I bailed on a failing startup and started freelancing. I did that for several years while the market was good for my kind of work, things started drying up and getting a little tighter around 2003 so I took a job and kept freelancing on the side.

Things got really good again and I decided to go back to freelancing again in mid-2004. Was offered a decent job in 2005, and remained employed full time (no freelancing) from 2005 through 2010.

In 2010, decided I'd had enough of the current job and went back to freelancing. Expected to have lean months while ramping up, but had more work than I could handle right off the bat. Then one of my anchor clients was acquired and jeopardized about half my income stream, and when a friend reached out about a job on his team, I took it.

Where this may or may not apply to your situation is my line of work has no major startup costs. I didn't have to rent a location or buy a lot of equipment or make large investments to get started. So the worst-case scenario is not making enough income, not losing a big capital expenditure or (worse) going into debt.

If you can start on a shoestring, especially if you can trial-run your business idea while still employed, you don't have many reasons not to try.

My rule of thumb is this: under no circumstances try starting a business or freelancing without primary employment if you don't have at least six months of cushion for mortgage/rent, food, clothing, and all that. Preferably a year.
posted by jzb at 6:24 AM on June 20, 2019 [2 favorites]


This question is very interesting to me, because at first glance it seems like a perfectly normal one, but the more I think on it, the more I realize that the opposite of Step 5 are the stories that might be harder to find. The world is full of possibilities and alternative life paths. We are never too old to pick up sticks and find new ways to make our living. Human ingenuity is vast; we can thrive under conditions we never expected to be able to handle. In our imagination, we tend to equate failure to The End, but it's almost never that.

Some of your fear can be untangled by simply defining what you mean by failure: if you're back at some boring job that pays maybe a bit less than what you were earning at your first boring job, is that a failure to land on your feet? But the other, bigger part is about trusting that you will be able to stand back up again even if you do land on your ass. What's truly rare is folks that crash landed in such a way that they lost the use of their legs forever.
posted by MiraK at 8:04 AM on June 20, 2019 [2 favorites]


(PS: none of the above is an argument for not preparing your safety net or not doing due diligence in every way possible; just that there will always come a point when you must stop preparing and take a leap of faith in order to do the thing you want to do. It will never feel safe enough and it will never BE safe enough for our comfort.)
posted by MiraK at 8:08 AM on June 20, 2019


Response by poster: ^^^ That's an easy thing to say, but it doesn't really help ease the mind, especially if you're prone to anxiety. My hope is that reading the details of steps 4 and 5 will be kind of like imaginal exposure therapy. And it's the details I'm interested in, not just "yes, it's possible". For example, once you start thinking about thinking about closing your business, when do you start applying for jobs? If your business is a coffee shop, do you go back to your original industry, or do you start looking for jobs in the coffee industry? How do you talk about the process to your in-laws?

As an analogy, I also know that it's extremely likely that I'm going to eat dinner tonight. But what? And how? For me, that doesn't provoke much fear, because I'm a pretty good cook, I have a kitchen overflowing with food, and I have plenty of money to go out to eat if I don't feel like cooking. But what if nobody had ever taught me how to cook, and I also didn't have any money to go to a restaurant or buy groceries? I could always just have faith that somehow, food will make it into my stomach, but it would be much easier to focus on other things if I had some idea of what that mechanism would be, you know? Maybe reading some basic recipes, or finding out if there's a food bank that would serve me, or whatever.

That's kind of what I'm looking for: answering these nagging questions so that I can focus on other questions, such as the exceedingly minor question of what my business would actually sell or do. :)
posted by kevinbelt at 10:06 AM on June 20, 2019 [2 favorites]


I like this question - I've often wondered about the same thing, because most businesses aren't built with VC money or the spare trust fund, and in a lot of cases the people left holding the bag are not so well off that they can take the hit without pain. It's easy to say economic failure won't kill you (though in the US, given the healthcare situation, that's even less clear than elsewhere), but what happens when you lose more than you can afford, and how can you keep that from happening?

I wonder if there's a small business assistance or mentorship organization in your area (something along these lines) that might be able to supply you with realistic examples of both success and failure. I knew someone once who volunteered as a mentor to people opening their first businesses, and he said the main advice he gave people was not to do it, because most people were going into it with poorly-considered business plans and expectations. I think someone who's accompanied many such attempts would have useful insight into what you can expect, what you would need to prepare and plan for to do things right, and how (or whether) you can realistically protect yourself and, as you say, land on your feet.

If you don't have that kind of resource available, another possible approach would be to have some consultations with accountants who specialize in small businesses and would be able to speak to the aftermath of a business closing.
posted by trig at 11:05 AM on June 20, 2019


As for material to read while at work, if this is something you're serious about I'd check out (e-)books or online classes on how to start your own business, as well as any material on the websites of organizations like those linked above. They may or may not have the stories you're looking for (I'd think at least some books would), but they should give you a sense of the resources you would need to put in and whether you can afford that.
posted by trig at 11:15 AM on June 20, 2019 [1 favorite]


Well, I didn't start a business but I did leave a marriage taking two kids with me, after having been a stay-at-home mom for 7 years, one year into my first full-time job where my contract was ending in two weeks - no next job in hand.

What helped me do it was:

(a) having absolutely made up my mind to do it -- after vacillating for eight solid years (trying different strategies to make the marriage work, going to counseling, etc). The point here is: you'll take the plunge when you're ready enough and you're motivated enough. It's okay to trust yourself to do it when you are ready.

(b) a lot of prep work in the months before it -- I prepared for the possibility of being divorced and without a job even before I properly decided to get divorced (while still in couples' counseling) by secretly saving 75% my paycheck for the whole year before it. I lied to my husband about how much money I was making to pull this off. I saved enough to live on for a year (health coverage included, plus the extra childcare costs if I had 100% custody). That's the way my anxiety works. I am prepared af for the worst case scenario. If I hadn't hadn't been prepared, I would not have left... in fact, not being prepared was the reason I didn't leave for at least the last two years in spite of how increasingly abusive the marriage had become. -- Point being, don't take the plunge until you have a very comfortable cushion.

(c) throwing everything I had into making best case scenario happen after I left -- my ex was abusive but I never once said so to him. I acted sweet and kind and nice because my eyes were on the goal of "smooth transition for the kids." I would have sold my soul to the devil if that would train my ex to co-operate during those first few turbulent months. As it was, I lied, smiled, cooed, cajoled, sympathized, took all the blame, listened meekly to his rants, faced his mother's wrath, agreed to unfair conditions, gave up a ton of assets, etc. And I also stood firm when needed, used my lawyer as a shield against his threats, stared him down and shamed him when he behaved in a way that affected the kids. Carrot and stick, whatever worked. It was ridiculously difficult. But no regrets! I did what needed to be done to safeguard my kids from having an angry uncooperative dad. --- the point of this list item is to have a certain goal in mind for your ideal scenario, and then sacrifice the fuck out of everything else to get there.




When first entertaining the idea of divorce, eight years before it happened, I asked the very kinds of questions you are asking. Eventually, after going round and round in my head endlessly about these questions, I realized that in general, it was best to leave every possibility open to myself.

e.g. If I lost my job, what was I going to do? Apply for jobs everywhere in my main field - yes. Apply for other random jobs in shotgun fashion - yes. Apply for aid at women's shelters - yes. Get a part time job at Starbucks - yes. Sell my wedding jewelry - yes. Use the jewelry money to pay for a lawyer to take my ex to court for marital assets/child support - YES. What sense does it make to say, "Ah, I will do __ and __ but not __ and __"? Especially years and years before the fact of actually being in the situation?

That's what I meant before when I spoke of possibilities and human ingenuity and all that. You don't need all the "actual" answers right now. What you do is you prepare for two possibilities, the best one and the worst one. That's all you need. Truly.

These "optimizing" questions -- such as do you go back to the original industry you were in or do you leverage your new business expertise -- and the "theorizing" questions -- such as what to tell your inlaws -- are of no use to you NOW because there's far too many variables.

Like the inlaws thing, I mean, I had to tell my ultra-conservative parents that my marriage which had begun with elopement against their wishes was ended. There was so much emotional work I had to do around telling them -- e.g. I had to let go of the idea that of pleasing them, I had to be okay with them thinking of me as a failure, I had to prepare for their anger or vituperation, I had to strategize to make sure they could not fuck things up for me by medding with my inlaws or my soon-to-be-ex husband. I simply had no room to think about this and process any of this while deciding or while telling my husband that I was done, but I DID have the time and opportunity to think about this immediately afterwards, while I packed up my home of eleven years and moved into a new apartment. It could not have happened at any other time. I would have had no clue what to think during the years when I was saving up money "just in case", for example.

It's like... you don't need to figure out what to eat for breakfast on the morning of the day you shut your business down, like, what if you feel too depressed, should you make oatmeal? And on the other hand, what if you are nauseous, should you eat dry cereal? You aren't Dr. Strange and you don't have the fucking Time Stone, man. You aren't going to be able to look through 14 million possible futures and figure out the one optimal set of choices. Even if you could, it wouldn't help you do the emotional work you need to do to truly come to terms with these choices. That only happens as you go through them, in live-action time. Leave it be. You're just feeding your useless anxiety when you think about these questions.

Focus instead on the fact that YOU WILL FIGURE THIS OUT AS YOU GO ALONG.
posted by MiraK at 11:52 AM on June 20, 2019 [5 favorites]


I started out in college working toward a career in Journalism. When I graduated, I was sufficiently versed in early web tech that I got my first professional job for the new website of the local daily newspaper. I coded, I wrote, I did graphic design, I learned new stuff. At that point I left the field of Journalism behind and went toward web tech. I stayed in web tech, gravitating more toward graphic design and marketing but still almost entirely web-based through several more jobs and a stint freelancing until the market for web work took a nose-dive. I got laid off. FAILURE.

While tech was in the doldrums, I freelanced and worked both for myself and on contract for anyone who was hiring. We moved from a nice apartment to a shitty-er apartment to save money. I did this while taking a few community college classes and art college classes. I wasn't sure if I wanted to throw myself head-long into higher levels of graphic design or...something else. I took classes in sculpture, economics, figure drawing, history and architecture. I got really taken with architecture and ultimately decided to pursue it as a career change. While tech was at this point coming back, my interest and drive for it had waned. I went to grad school for Architecture and got my Masters. I graduated and the industry was booming. I got a great entry level job at a large-ish firm doing some interesting things. I didn't want to stay there forever but it was great foundationally for me. Then, guess what, building boom busted! Houses in foreclosure. Building halted. My biggest project at work put on a shelf. I got laid off. FAILURE.

Both times, I took unemployment for as long as I could. The building services industry was really in a shambles. I tried hard to find more work but there was less than nothing available. My husband's job was still going strong so yay for him. Somehow he never gets laid off. I took the opportunity to do some odd jobs by networking among my friends. I spent a year seeing if I could find inroads into the cheese industry and used my considerable craft beer drinking talent to good use by putting on paid beer and cheese tastings events. Yum! I never did really launch anything with that but it was really fun. Eventually, I connected with a local architect who needed help with her residential work and started contracting for her. I also had a baby during this time. Who needs maternity leave when you're already unemployed!? After a few years of freelancing and first-time-momming, I started looking for full-time employment within architecture again so I could finish my licensing requirements. Got a lot of interviews but things were still slow. FAILURE.

I spoke with some friends about working for their web shop as a project manager. I convinced them that my entire background would naturally make me a good project manager in tech web marketing. I was right! However, that place was horrible. I quit or was fired, hard to tell. FAILURE.

Another friend had a web/tech/marketing company and lost his project manager. I worked there for two years and spent that time really honing my interests in business strategy, time management, communication, and learned Scrum which I really enjoyed. I was starting to look around for the next thing and try to figure out what the heck I wanted to be at this point when some other friends from grad school talked me into coming to work for their little boutique architecture firm. It was a total mismatch. I quit or was fired, again hard to tell. FAILURE.

At this point, building was booming again. I saw how my friends were running their little architecture firm (not well) and realized that I had an entire well-developed skillset for running my own business which I've been doing ever since. I focus on home remodels and additions and I really and truly enjoy it. My year 1 income was about 1/2 what I could get full-time at an architecture firm but without a zillion of the headaches and with lots of cost savings. I had also saved a bunch of web/tech money and put it aside for two years. I had a full year of my income in the bank to tide us over. Year 2 I earned about 150% of year 1 and here in Year 3, I'm making more than I would make at the same level in an architecture firm but I'm also working kind of constantly and I need to hire someone but that stresses me out...so. If I "fail" or close my business then I'd be looking to go work for a small residential architecture firm. Or, I dunno, learn how to clone dairy goats or something.

One more anecdote in terms of action for you. During my time starting my business, I also did a little products-by-mail business with a motivated partner. She'd never started her own business but had a great concept and a lot of energy. So we partnered and worked through all the details together, her with her specialized knowledge of the products and me with the general business knowledge which including packaging and mailing (from another small business venture of mine with a product that I designed, sold, mailed, broke even, made a small profit and then quit) and various tech stuff like websites and mailing lists. Key though was this: what's the minimum viable product that we can create in order to accurately test this idea? We kept focus on that, intensely (it's easy to get carried away), and did a Christmas season soft-launch with orders and sales and fulfillment. After our expenses (and not counting our time!) we each made about $120. But, truly, time was the killer. Neither one of us were going to give up our "day jobs" although if it really took off like wildfire, we could have considered it. But in order to even get with the wildfire, we would have had to find a way to devote more time and money. We each committed $500 in starter cash at the beginning. And we didn't lose any money. FAILURE.

So, if you want to start a thing without risking everything. Here's a few things you can do: save your money, leverage your current workplace to learn as much about everything you don't know about running a business, use your spare time to explore your business ideas, take a class, go to SCORE or your local small business office and see what classes they offer, see what would be the most minimal thing you can build or put together to start "market testing" your idea. Once you are ready to commit to something, make sure your spouse is on board, especially if they are your safety net! Don't take on loans and don't quit your day job until you've done the work.

I love everything MiraK has already shared.
posted by amanda at 1:57 PM on June 20, 2019 [3 favorites]


By the way, I hope you've given some thought to the fact that if you start a business at the same time as when you have a baby, and you don't build a humongous amount of family time into your plan, that might blow your life up in ways that genuinely cannot be fixed. Your baby's going to need you. Your partner is going to need you. Your other kid's going to need you.
posted by MiraK at 3:08 PM on June 20, 2019 [2 favorites]


Definitely incorporate the business - if it fails, it goes into bankruptcy, not you.

My dad started his own shoe+luggage repair/ leatherwork shop and got it profitable but it was a lot of work. He somehow found someone who wanted to buy it from him in some sort of investment immigrant thing, so he happily sold it (and switched to being a private violin teacher). They were terrible at it and just poured money into it for the year that was required by the immigration program and they just up and abandoned it.

So, I guess know when to pull out. Try to avoid the sunk-cost fallacy if things get rocky with reasonable light at the end of the tunnel.

Going back to a cubicle job - I guess it depends on what kind of specialist you are and how the experiment in running your own business ends; try to spin it as a positive ("I got the entrepreneurial bug out of my system, I work better with structure/ part of a larger team/ etc.")
posted by porpoise at 3:12 PM on June 20, 2019 [1 favorite]


Things I learned:

Don't turn your hobby into your business. You will no longer enjoy your hobby, and you will not have a relaxing hobby to fall back on after a long day at work.

A lot of my identity was wrapped up in my cubicle job, only I didn't know it. I was really really good at that job. I was not good at owning my own business. That in and of itself is okay, but what happened to me was that it created depression. The depression exacerbated my being bad at being a business owner, which contributed further to the demise of my business.

When it was time to give up the business and go back to work, I balked at the original plan I'd had when I quit the cubicle job, which was that I would just go back to my old industry. When push came to shove I absolutely did not want to go back to that industry. I spent a few years temping on various projects before I lucked into my current job, which I fortunately love. But those years were tough for the self-esteem, and tough on the marriage. For example, somewhere in those years we were thinking of buying a house, but we couldn't get a lender to count my income. My spouse was furious, and even these many many years later still occasionally brings up the idea that we should have been financially settled sooner in our lives. So some consequences can have long lasting effects.

I guess my points two and three are suggesting that you will need to build therapy payments into your operating budget.

Even after everything that I went through, I don't tell people not to try their had at running their own business. But my advice is this: don't jump in with both feet. Do something on the side. Work for a person or two who is making it work. "Intern" if you will with different businesses that are doing what you want to do. Build some interest, some loyalty. Let someone who is doing it show you how to solve the problems. When you've built it enough that you simply can't keep doing it in your spare time, that is the time to consider quitting your day job. But not before.
posted by vignettist at 12:33 PM on June 21, 2019 [1 favorite]


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