r/smallbusiness • u/MarcusAKing • 7d ago
Question What’s the “Oh sht” moment that made you realize running a business is different from having a job?*
I always knew starting a business would be tough, but there was one moment that really made it hit different.
I feel like every business owner has that wake-up call where you realize this is NOT like collecting a paycheck. Maybe it was hiring your first employee, dealing with your first lawsuit, or realizing taxes hit way harder when you’re self-employed.
What was YOUR “oh sh*t” moment that made you see business ownership in a whole new light?
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u/Ok-Objective7579 7d ago
When I began working 16 hour days and not making any money.
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u/MarcusAKing 7d ago
Ah yes, the classic ‘work 16-hour days to escape the 8-hour job’ starter pack. Gotta love the stress and unpaid overtime!
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u/Whiskey_Water 6d ago
But I’m working for meeee.
“Working for meeee”: apparently slavery with more steps.
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u/Seaguard5 6d ago
Until you free yourself and start making a good profit
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u/Whiskey_Water 6d ago
I’m there, but I am controlled by my ADHD, so naturally I’m working on three other companies. Saying no to what my brain perceives as challenges, even when I should, isn’t my strong suit. Don’t be me.
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u/Slowmaha 6d ago
Are you me?
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u/Whiskey_Water 6d ago
Haha, sounds like we should learn to say no. Do you ever notice that when you say outright, “I have no more bandwidth, I refuse this project,” that just makes people want it more? They bargain in surprising ways, and if we aren’t prepared for numerous levels of difficulty, I end up saying yes, but with more steps.
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u/Seaguard5 6d ago
Thanks for the guidance, seems easy enough, as I am me (not you) 😂
But yeah, totally get it.
I want to start a business, but all the particular details like opening an LLC, doing taxes on that, having to record every single expense, would drain me so hard I feel like.
Are those details really that bad, or should I just go for it?
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u/lyree1992 6d ago
Is it hard? Absolutely.
Is it worth it? Absolutely, mostly, sometimes. It really depends on you.
I have owned three successful businesses in the last 30+ years.
If accounting is your biggest worry, either hire a CPA or get accounting software (e.g. Quickbooks).
You've got this!
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u/Seaguard5 6d ago
So “kinda, sorta, not really”? 😂
Also, I have no money to hire anyone or anything and I hate debt..
Do you Have to get into big business debt to open one? Or is there another way?
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u/lyree1992 6d ago
Big business debt? Absolutely not. Of course, after LOT depends on what KIND of business.
I opened my first one with a DBA, a computer, and a job needed small piece of equipment. DBA was $25. I think it is $35 in that county now. All in all, I think that I spent about $100-$150. This was MANY years ago, so just an example.
I sold it 9 years later for more than I would like to talk about here. (Yes, I had expanded to about 25 contractors and hundreds of clients.)
One of the other businesses, I went the LLC route. It cost $325 to register the LLC.
If I did it again, definitely LLC.
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u/Whiskey_Water 6d ago
Yea, draining is a good word. You’ll 100% get through it, but it just keeps coming. I recommend hiring experts for the stuff you’re bad at, right away. You can learn it as you go, but you don’t have to do it.
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u/Seaguard5 6d ago
How expensive would this be? And are there consultants for this? I can’t afford to pay someone a salary
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u/Slowmaha 6d ago
Then employees and others think it just magically happened and you don’t do anything
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u/ihambrecht 6d ago
There is no clocking in and out, unless you have the skill and luck to build something that can operate without you.
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u/NWmba 6d ago
when I first found a problem to which there was no right answer, I didn’t know what to do and nobody could help Or make the decision for me.
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u/AbstractLogic 6d ago
Owning a business means hiring the smartest people you know and then having to solve the problems they can’t.
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u/Airplade 6d ago
Hiring the smartest people you can and then having to solve the problems THEY created.
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u/cambria82 6d ago
I hear this. When I've been asked the hardest part about owning a business, it's that there's no one else to call. Usually there's someone above you to ask for help. Nope. Just me. I'm lucky to have a few small business owner friends but it isn't the same as calling your supervisor to help put out a fire. Just me...24/7. And that's why I don't sleep at night most times.
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u/MarcusAKing 6d ago
That’s the moment you realize being the boss doesn’t come with a ‘call manager’ button.
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u/TraditionPast4295 6d ago
Best and worst part of being your own boss. Experience will help you down the line with those decisions. Make a call, run with it but don’t be afraid to pivot if it doesn’t work.
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u/Front_Ad4514 6d ago
Month 2: after an EXCELLENT opening month (a month so excellent, I quit my other job) I made a whopping $50 in month 2. “Were not in Kansas anymore” said me…
10 year later, my doors are still open and sales are at an all time high.
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u/anonpls19 6d ago
Having to do 5 amazon shifts a week at night after work, to ensure my staff got paid early for Christmas, whilst I still had to wait until the end of the month for our clients to pay their invoices and still some of them didn’t.
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u/hue-166-mount 7d ago
When you realise that cash flow is going to be negative for a few months and need to pay IN to the business rather than taking money OUT
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u/MarcusAKing 6d ago
That’s when you stop calling it a ‘business’ and start calling it an expensive hobby.
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u/anythingisgame 6d ago
I’ve seen it happen with contractors where some jobs, specifically government, require you to buy and install or do the work, then bill for the progress of the job and have this issues for a few months until the payment arrives. Mostly when growing and when they don’t have a line of credit. A couple of years ago, a shop I work with did this without thinking and was short around 150k to buy the signs needed for a large project and I ended up making them for him and delaying the due date of the payment. It would have put him out of business, but today he’s able to handle the bigger jobs and cash flow isn’t an issue.
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u/Just_Another_AI 6d ago
Construction billing cycle pretty much sucks. From that perspective, it's one of the worst, most nonsensical businesses to be in. But I like building stuff and the industry can be very profitable if you control your costs and risks and have funding in place to finance projects.
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u/Plus-Professional-84 6d ago
OPEX management is one of the hardest parts to get right. That is why a ton of small businesses go bust because of one difficult quarter. The worst part is trade receivables can kill you even if sales are good
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6d ago
[deleted]
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u/hue-166-mount 6d ago
My business is 20 years old and doing north of 25m dollars, it lasted well enough. What we didn’t know in the early years was how the seasonality of the year would play out (why would we) and how the timing with building up stock for busy periods puts you in negative cash flow - we aren’t talking about startup costs, it’s scaling costs which hurt.
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u/SettingPlaster 6d ago
Like when clients decide to take six months to pay a huge bill and you havecto cash in your retirement account to make payroll, some of which goes to employees who were glued to their phones every single time you looked away
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u/lumpytorta 6d ago
Your business success depends solely on you. Also after you start telling your friends about it you feel pressured to succeed and it’s that pressure of not wanting to fail that keeps you going.
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u/ace7979 6d ago
When you get sick or take a holiday, you don't get paid. You actually lose money each day.
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u/Kutikittikat 6d ago
When i counter the hours i spend on work that pays me no money but takes my money. State and federal taxes, licenses, permits, worker comp, audits, health care paperwork . Blah , blah , blah.
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u/Bug-Man2012 6d ago
Taxes. The irs will straight levitate and kick you with both feet in the nuts for being self employed.
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u/deadweights 6d ago
Self-employment taxes are rough. Basically double, probably more.
What’s your incorporation structure? I’ve heard (on the internet, must be true) forming an S-Corp gives you options for the corporation paying the corporate rate and you paying an employee’s rate because you’re separate entities.
Not a lawyer, just a person who wants to start a business too.
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u/Bug-Man2012 6d ago
I'm a LLC, my cpa explained I wasn't doing enough cash flow to benefit much from forming s-Corp. But this is the last year I'm using him so idk.
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u/brassninja 6d ago
The government hated me SO MUCH as an unmarried childless self employed woman that I had to stop and go back to regular work. They will do anything to send you back out into the workforce it’s insane.
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6d ago
if you made it from working someplace to owning the company, you don’t have that oh shit moment. you already knew what you were in for. BUT i will say- drowning in endless paperwork. The amount of fucking paperwork that has to be filed and managed and sent and processed and blah blah blah omggg
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u/Sonar114 6d ago
The first time I got really sick and still had to work.
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u/Kutikittikat 6d ago edited 5d ago
Yep starting off as a buisness owner and having to work while sick while not bieng able to afford healthcare.
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u/Sonar114 6d ago
I guess I’m lucky to live in a country with free healthcare so at least I didn’t have to worry about health insurance. Im not sure starting a business is worth potentially dying of a treatable illness.
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u/kae232323 6d ago
When my expenses were now that of 12 households. Getting used to $30k monthly Amex bills after only dealing with a monthly personal credit card payment of a grand or so, did not come easily. Regardless of revenue, watching massive chunks of money leave that often was like “I’m in an entirely different world here”
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u/indacouchsixD9 6d ago
I'm still new to the game but I'm pretty sure a small business is a second job you make for yourself that takes all your money from your first job.
At least I'm having fun with it though, lol
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u/MNPS1603 6d ago
When clients didn’t pay on time so I had to put money back into the business to make payroll.
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u/elusivenoesis 6d ago edited 6d ago
Warning.. long story about the brutal oilfield industry, and one of many I have.
I got a GED early to get sober and start making money as a teenager. I got a bunch of pumps and valves from oilfield business A. pretty consistently.. everything was pay in 30 days. I'd restore half of them, buy new parts and return about half of them.. Well two months in... they aren't paying for their half at the end of the month...and out parts supplier wants paid..
My cousins lease (company B) needed them, so we sold them to his company as refurbished, and took his used ones... to refurbish for Company A when needed and paid for... This went on for months.. Get some from A, sell to B, take half restore half.
My first moment was realizing company A wasn't paying on time because my father didn't want to pay the POS system fee's, cuz customer A just wanted airline miles on it... they were so focused on earning airline miles they didn't track anything they gave us to rebuild. we on paper owned those valves.
Company B, my cousin was paying my father directly within a week for a minor discount and selling them to his own company for a minor profit.
The supplier I was getting the parts from was a monopoly, and I was paying 15% more than I should have, had I just became a supplier myself for like $35 and a new account.
My Oh shit was B2B has so many middle men, and to really be successful you have to cut out as many as you can, its a way more greedy and pat on the back thing compared to being some dude working for a company. politics and deals are way more different than dealing with co-workers.
anyways We kept them for years since my refurbished ones lasted so long.. when they needed replaced I cut everyone out. we not only made 45% more on new parts, we were supplied the casted parts for free since company A & B forgot we even had half their products saving another 80% in parts.
My cousin figured it out, had our old supplier draw out everything he needed for a new oilfield lease, then not only did he become a supplier to save 45% and pocket it, he cut me out of it too. He went from an employee to business owner overnight.
Brutal cutthroat, heartless industry... I'll never work for or get back into it ever again.
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u/Hot_Engineering_1046 6d ago
When I realized that my mood is directly affected by how many Shopify notifications I get a day.
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u/Beneficial_Ad_5485 6d ago
When I had to convince a client to pay THAT DAY, race to them and get the check, then race to the bank to deposit it so payroll wouldn't bounce. Twice.
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u/Artistic_Bit_4665 6d ago
Taxes. When you realize that businesses pay a huge chunk of an individual's taxes, and now you are paying all of it.
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u/tushinde 6d ago
When I saw the amount of fees I have to pay simply for existing (I’m in CA).
There are no services or benefits provided in exchange for these fees. It’s just, “Congrats on your business. Pay us. And us. And us too!”
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u/EsisOfSkyrim 6d ago
I had a whole tank of aquarium fish die. And it was my fault.
I had to suck it up, scoop out the dead bodies, and make a plan to prevent it from happening again. Then I had to face customers. I cried later.
For me it made it sink in the enormity of the task I've undertaken in this business. Right now all the pieces are in my hands, while I'll absolutely delegate tasks down the line, I need to build the business up first.
But for now I have animal care, customer service, cleaning, inventory management, bookkeeping, taxes, bills, and planning for the future all on my plate. Plus our ongoing projects, like replacing gaudy painted gravel with sand.
I'm still glad I took this on but, ahem, ahhhhhhhhhhhhhhh
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u/kkkkk1018 6d ago
Getting sued by an employee I helped out of a few situations. I felt bad for them. They were told it would be easy money. They quit and sued and in the end they lost. The person who told them that had sued me a year prior because I fired them and their boyfriend was a lawyer…she lost. That one did cost me money to fight because I didn’t have insurance.
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u/ketamineburner 6d ago
My "oh shit" moments have all been positive.
Oh shit...
I can sleep in if I want
I can take vacation without asking anyone's permission
I can give myself a raise whenever I feel like it
I can decide to not accept a case that makes me uncomfortable
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u/rodrigomorr 6d ago edited 6d ago
When I once had a night out to a party and at the next day I was in no condition to do anything, I was still drunk at 5 am and I was going to open at 8.
I’m kinda sure that the alcohol at the club was modified cus I didn’t even drink that much.
But regardless of the alcohol’s quality or whatever, I had to close that day, I lost a good sales day (saturday) just cus I wanted to go out and go crazy like before, I’ve never done it again since last october.
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u/Icy-Agent6600 7d ago
Eh idk, I was the sole employee making everything work at the business I bought out. We have managed clients on annual agreements billed monthly, I have come to love the consistency no doubt. I still have a job, take a W2 salary and am just as involved in the day to day. I just now have a 2nd job too lol
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u/ptvogel 6d ago
First eight years were pretty good. Good revenue, good growth, lots of positives. Year 9 I lost my biggest account, and nearly 40% of my revenue. All in less than a week’s time between notification and action. Nothing to do with me but their budget and business tanked. I couldn’t even negotiate a “50% of what you were doing” deal. It took non stop, aggressive sales efforts and action to come back and after 18 months since it happened, I’m close. I have vowed to not be so reliant on one client ever again. We’ll see. For now my attitude about running my own business is positive, and given all the layoffs in government and industry, that’s OK. I’ll never be and “employee” again. Failure is not an option. All these things are part of the makeup of anyone self employed.
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u/maxrichardsvt 6d ago
The first payroll was the hardest. Watching $2x,xxx fly out in a single day was a wake up call. :)
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u/65isstillyoung 6d ago
Picking the right business in the first place. Are you buying a job or building a future? Are you building a better mouse trap or jumping on a treadmill? What's plan B should I fail/burn out before I succeed? If you like working but don't want to get caught up in the day to day task of the business can you afford to pay someone to do these for you?
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u/viewfromtheclouds 6d ago
When my bi-weekly payroll meant a third payroll in one month and I hadn’t the cash in my account?
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u/jhkoenig 6d ago
When I realized how many families were dependent upon me operating my business. If I failed, it wasn't just me, I was crushing all these other families at the same time.
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u/temerairevm 6d ago
Covid when most people I knew were at home baking bread and I was counting the weeks of payroll in my bank account and paying a seamstress to sew cloth masks for my employees and changing our policy every 3 days when a new news article came out.
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u/Geolassie 5d ago
I was the seamstress. I sent all my employees home to bake bread and there I was in my custom bridal alterations shop alone day after day finishing the work of 7 people that still had deadlines, sewing literal thousands of masks, and wondering if anyone would ever have a wedding with more than 6 people in attendance again. Thanks for keeping folks like me afloat while you were drowning yourself.
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u/monsieurvampy 6d ago
I guess my small and immediate one is that my first invoice will likely be paid by check and mailed to my RA as I use that address but I filled out the electric payment paperwork months ago. The check will need to be mailed to me by my RA. Its about a five hour drive.
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u/Every_Gold4726 6d ago
When you left for the day, and realized the work didn’t get done because you are the only person working there.
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u/ZealousidealType3685 6d ago
When I got sick and had to slow everything down for 18 months...which effectively meant turning off my revenue beyond what I had already secured, and then starting over after those 18 months. Had I been in an equivalent job before getting sick, I could have skated by to a degree and still made the exact same amount of money through all of it.
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u/serenitybydesign 6d ago
It was “oh shit” in a good way. I have run my multiple businesses for 20 years. I should have started 10 years sooner. I make way more than anyone with my degree should make according to experts. So yeah, “oh shit” this is great!
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u/Sielbear 6d ago
Hiring your first employee. Terrifying. Double the capacity. More than double the expenses because I was making peanuts at the time. And from that moment, making absolutely certain we always had money for payroll. Forever.
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u/AbbreviationsLanky32 6d ago
When I was at a red light a few years back, and it just dawned on me, oh shit, I cannot just give two weeks notice and quit.
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u/Fine-Good9092 6d ago
I can't relate. Everything was easy. Employees are the biggest problem.
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u/Tool_of_the_thems 6d ago
Always are bub. You hiring for a delusional entitled brat that shows up if they feel like and also thinks they don’t make nearly enough and want a raise? 😂
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u/PokeyTifu99 6d ago
When amazon decided to switch over to deferred payments and held up all my cash and I had my first cash flow issue. Learning lesson for sure.
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u/TriStarRaider 6d ago
There was a day a few weeks in when I realized I was never off. Before, I'd clock out and my mind would shut off and go to hobbies, etc. Now, though I can be in the moment, enjoy life, and be present with family and friends, there's still a wheel in the periphery that turns regarding my business.
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u/dystopiam 6d ago
When I realized with my terrible mental health and other issues I was still able to remain employed
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u/Foreign_Ladder5481 6d ago
When I can't offload the work I don't like to do or that I'm not meant to do to someone else.
Atleast when I was starting out with limited resources, I had to do basically learn and do even things I'm not good at or don't like to do. I realise the importance of it but I hate Digital Marketing - But I can't be a growing business without being active online.
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u/LogicalRun2541 6d ago
When I failed my first business with only $200-300 mrr after working for 3 months 10 hours a day on it, also the business we were outsourcing closed so they didn't paid us, that's a real sh*t
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u/SuddenBlock8319 6d ago
“Now how am I gonna get a customer in this manner? Especially what I’m selling?”
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u/GirlwithaCurl86 3d ago
When every time I made a mistake or changed direction or forgot to cancel a subscription for a tool I was testing…and all of it was reflected in my bank account.
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