How do you decide to quit your safe job and go into business for yourself?

No, they’ll scream bloody murder and have to be removed by security. The fax machine won’t be broken, the one on the other end won’t be turned on. The point is, decisions are made higher up that affect front line staff, but nobody consults the front line staff.

If/when you run your own business, you’ll be the higher up AND the front line staff all rolled into one. The patrons at the library are your current clients… With your ow business, your potential future clients will still be screaming bloody murder when something doesn’t work the way they think it should. They just might smell better while doing it.

You’ve just opened another can of worms. Ask yourself this.

Your hypothetical company has X as a client. X pays slow and your company always seems to give them more than the contract calls for.

You say to your partner, “X isn’t paying, and even when they do pay, we lose money on every project we do for them. We need to dump them.”

Your partner replies, “No. X always pays sooner or later, and Joe has promised to send us more business and we’ll be able to raise our rates then.”

How do you resolve this?

Now, let’s say it’s 3 months later and X has gone out of business, sticking you with a lot of unpaid bills. Your business partner also happens to be your boyfriend. Does your displeasure with his business decisions spill over into your relationship with him at home?

I’d like to comment on a different part of the OP.

I’d never make a job or business decision that included an inheritance as part of the calculation. I’ve seen too many older relatives do this and then get disappointed one way of another. End of life care can be extremely expensive. And people remarry. It’s just too uncertain to depend on.

I think this is a wonderfully thought-out OP, but I will have to agree with the crowd that this doesn’t seem like a good idea at this time. The advice that things should be going so well that your SO NEEDS your help to keep up with business seems good. Instead of hiring salespeople, he should need some back office people to produce the stuff that there’s a demand for. He should be the salesman - the one who is passionate about the work and has a stake in whether a sale is made or lost.

Instead of looking to head to an uncertain new business, perhaps you should look into other jobs in your area that you might have more passion for. You have a great education that would prepare you for many interesting jobs that, you know, pay.

I’m going to play devil’s advocate and say do it. Quit. Help your boyfriend. Worst case scenario, you get in debt and spend a few years paying it off.

You only live once, and every year you spend wasting away at a job you hate is just not worth it.

I quit my job, a nice stable one as a supervisor at an insurance company. I was their full-time web designer and kinda-sorta-art-director guy. It paid well but it was far from creative or fulfilling. I didn’t hate it, but I also knew that I’d be pretty unhappy if I worked there for 30 years and retired too old to enjoy the retirement benefits and pension.

With help from my wonderful girlfriend, I quit, while she promised to help cover the bills if I had slow months in my freelancing career. Meanwhile everyone told me I was insane for quitting my job during a recession and there would never be a harder time to start a business. I agreed, but if I waited a few more years, I may have children and couldn’t do it then. So it was now or never. I put my notice in.

That was about a year and a half ago. My little freelance web design business has gone amazingly well. I started out underbidding, using low prices to under cut everyone and get a ton of small clients. I built my portfolio. I did good work. I had good customer service. Slowly but surely, I started making more money, getting more large jobs, and got more financially comfortable. Like ZipperJJ, it was many sleepless nights, long hours, and poor wages. Lots of Ramen meals and Mac and Cheese.

But, at the same time, it was incredibly rewarding. The jobs I got were my own. I was making my own schedule, choosing what I wanted to work on and who I wanted to work with, choosing my rates. I was working my ass off, but I’d never been happier.

A few months ago, my wife (the same girlfriend that had encouraged me to quit) was unhappy at her job. I decided she should also quit and help me out. She did. I raised my rates again, by quite a big percentage, and my clients paid it. My wife, a trained social worker with no passion or knowledge of web design, helped me with things like billing, invoicing, marketing, writing, social networking. She doesn’t love it, but she loves it infinitely better than what she was doing before. With her help, I have gotten a huge, huge client that I am completely excited about, and she feels fulfilled that she helped “our” business in that capacity.

If you would have told me 19 months ago when I was working at an insurance company where I would be now, I wouldn’t have believed you. My business is thriving, my wife is helping, our bills are paid for. None of it would have been possible if we didn’t both take a bit of a risk. And even now, I am fully aware that it could all go away tomorrow, and even with that doubt in my head I have never been happier, and neither has my wife. Meanwhile, if our reservations and fears would have kept us in our unfulfilling jobs, we would have spent the last 2 years a little less happy, and the next rest-of-our-lives wondering what would have happened if we hadn’t taken some initiative.

Good luck.

Here’s my issue with your scenario as an example. You quit your job and your gf/wife helped cover you. And then you did well.

Then she quit and you are doing better.

That’s a great story. And I’m really happy for you! Really!

But it’s apples to oranges.

Her bf is struggling. If she quits her job, there won’t be someone to cover them, like your gf did for you.

If it was your scenario - I would tell her to go for it also.

But she’s not.

One of the primary reasons small businesses fail is the owners don’t properly focus on their jobs. Running three businesses means you’re already looking in three different directions at once. Unless the BF is running as a some sort of joke candidate, there’s 20 - 30 hours a week spent campaigning. There aren’t enough hours in the week to do all this.

The BF needs to concentrate on doing one thing right and maybe, in time, the rest will follow.

All this IMO, of course.

Well, kind of I guess. 4 or 5 months ago, I WAS struggling pretty hard, and between her consistent paycheck and my really weirdly inconsistent money, we were barely making it, playing those fun games where we skip a bill one month so we could pay another, then the next month we’d skip another to pay the one that was 2 months late. It was fun stuff.

When my wife decided to quit, THAT was my motivation to do better. I did more sales calls, I bid substantially higher on jobs, I made a lower per-dollar rate to do better work as a benefit to my portfolio so I could then charge more for my next client. I followed up with my non-paying clients who had gotten a pass before because I was so busy. I made changes to my contract and payment terms to ensure a more consistent paycheck. I redid many of my marketing materials because I had a lot more time with her taking over a chunk of my work. Without her kick in my ass, we’d still be struggling.

And don’t get me wrong, it is still a struggle sometimes, but we were struggling before too. If she thinks she can benefit her boyfriend’s company in the same way my wife benefited mine, I think she should do it.

Also, for the record, my income now that I’ve raised it to cover her lack of paycheck, is just above what I was making at my insurance job. So no, financially we are still not as well off as 2 years ago, but so what? All it means is cutting some corners. We eat out less, cloths have to last a little longer, our date nights are home-cooked meals and rented movie instead of fancy restaurant and theater with popcorn. You can make it work.

My friend’s husband quit his stifling corporate job, and its 6 figure income, plus profit sharing, plus insurance to pursue his dream job 2 1/2 years ago. I just saw them at a party. Wife is back to work because his dream job didn’t pan out and their stress level was palatable. His self-esteem was shot.

The stats on small businesses failing are staggering.

Ideally, you should keep your full-time job and pursue your passion on the weekends and evenings until it flies. If you don’t have a minimum of 18 months cushion in the bank to tide you through, plus access to insurance, then it’s incredibly risky to leave stability for uncertainty, ESPECIALLY in this economy because once they fill your job, it might not come around again for a long time.

I think quitting sounds like a really bad idea. It would be good to have the steady income while your BF runs his business. Especially if you are loaning him money.

When you say “preliminary reasearch” what does that mean? Has he put together an actual business plan? What do his cash flows look like? How much capital does he need (including your “loans”)? What does his market really look like? How long can he stay in business?

The way you make these decisions is to sit down and look at the hard numbers.

He has a business plan, of course. It needs to be redone, though, because it’s been a few years and of course the economy and everything has changed.

Current small business owner here. It sounds like he is already running a little ragged.

My question is this…hes having trouble paying the bills but he has 3 employees? If there is not enough work to justify the staff maybe he needs to look there for some relief. Employees are expensive no matter how you slice it. We just added a body at my business because we were running 12-14 hour days for weeks at a time, we were turning a profit, and we were unable to capture many of the clients that called because of 2-3 day waits for an appointment (onsite computer repair).

Its only been 3 weeks and we are usually rolling within 4 hours, almost always by the next day no matter what. Because we were already profitable, now we are seeing more money rolling in and the workload is much better distributed. IF there is no work, he needs to look long and hard at his employees and if they are helping as much as they are hurting.

One quit yesterday (constant personality issues) and they’re actually thinking it’s going to be a blessing in disguise - he’s going to tell them all that they can either replace her and work longer at less pay to get rid of their debt, or they can work harder and get a raise sooner.

They’ve recently started working a lot on their efficiency, which is starting to pay off, but how much he can pay them is a constantly limiting issue - you’re only going to get so much work out of people if you can’t pay them more. My suggestion, that he remind them that state unemployment is 12.5% and that they’re lucky to have a job at all, wasn’t really met enthusiastically. :slight_smile:

Comments like this make me question whether either of you can effectively manage people at all. Although I assume you are joking. I once suggested to our managing director that “making this a sort of place where people want to work here” just gives our employees a big head and makes them think they are more valuable somewhere else and that we should be crushing their spirits instead. He then called me a bastard and passed out on his face (we were drinking at a bar at some corporate boondoggle). But I digress.

The thing to remember is that it’s not your employees debt. It’s your boyfriend’s debt. Employees just want to be paid and treated with respect. I you treat them like you are doing them a favor by allowing them to work for you, you’ll find that the only ones who will work for you are the ones that no one else will hire.

Failure to meet cash flow demands and payroll in particular is the biggest reason companies fail. One alternative to reducing headcount (which also has the unfortunate side effect of reducing your maximum productivity) is to raise your rates. If you are already working as hard as you are and struggling, that might be an option.

Coincidentally I was talking to a couple of friends of mine last night who do free-lance graphic design and whatnot. To me it doesn’t seem like a very scalable business.

Scalable, no, but who cares? As long as you’re happy doing it and the bills are being paid and you enjoy your lifestyle, what else are you looking for?

Also, for the record, there are plenty of what’s called “six-figure freelancers”. They get good money in addition to being able to make their schedule, choose who they work for/with, etc. It’s tough for a guy like me to think of a better life to lead.

This doesn’t sound good to me. To whit:

  1. He has three businesses. And wants to be a mayor – not seriously, but still trying.
  2. He’s borrowed 10,000 from you and you haven’t seen a thing.
  3. He wants you to be an office manager. This is a boring job. Trust me.
  4. You need your insurance.

Guy sounds like kind of a flake. He’s draining you of your resources and wants more, all of your money and time and effort. This would be fine if you wouldn’t be in danger of losing what you’ve got. You DO have a good job, you DO have benefits, you DO have a house. You want to give all that up? Really?

Kind of sounds like to me you’re so disgusted by your current job you want to wash your hands of it, and this idea of jumping head first into a struggling business is just the excuse you’re using. Someone wants to buy a fax machine and that is the last straw on your back.

I advise you to wait two months and look again. Really evaluate your relationship with your boyfriend, and look at the long term prospects of this business (that already has had legal problems!). I don’t want to say you’re being hasty, but I think your annoyance with your job is feeding a lot of your desire to go work with your boyfriend. He’s probably nagging you to do it, too (free labor).

I’m torn. On the whole I’m thinking it’s a bad idea.

My husband and his partner started a business about 2 years ago. Software. It went really quite well for 18 months–they worked all the time and never made as much money as they were supposed to, but we got by and expected things to look up. There was no debt and no VC, and we were OK. Then a year ago when the economy tanked, all the clients evaporated. The contract that was supposed to pay for our bread and butter for the next two years disappeared. And there was no unemployment money. My husband worked very very hard on getting new contracts and searched for a job at the same time. No one was hiring. He finally got a good job a few months ago.

We scraped by, just barely. We came closer to foreclosure than I ever want to be again (and I was thankful every day for our small mortgage–well by CA standards). We have a ton of debt that is going to take a long time to pay off, and we owe my parents money too, which I hate. We got food from our church for months. We haven’t taken a vacation in years, and don’t expect to for years more. We have almost no savings any more and we are 36.

Now, I don’t regret all this. I supported my husband in it and I still do. But we got lucky, getting a job right before things went all to hell. We could have lost everything. And I didn’t work for him–I’m a librarian too, but I was extra help, and I got laid off right when I wanted to work as much as possible to earn some money. There were no jobs lying around waiting for me, so I concentrated on managing our family on as little as possible.

This is a really bad time to give up steady income in favor of a small business, and it sounds to me like he really needs to focus more and get more contracts himself before he spends money he hasn’t got. Don’t go into any debt if you can help it. Just don’t, and manage on what you’ve got.