As a freelancer, I’m pretty darn lucky. While my husband also freelances, doing web developer/design work in the evenings and on weekends, he still has a full-time job, which provides the two of us with both health insurance and some semblance of financial stability. It’s a luxury that I know many freelancers don’t have.

So my feelings were understandably mixed when, just the other week, Michael laid out his grand, master plan for leaving his job and starting up his own business with a fellow web developer. “We could probably have this set up within the next few months!” he said.

While I’ve been urging him to make such a move for what seems like eons (for the sake of his own sanity and happiness), my initial excitement was quickly tempered by sheer terror.

The items listed after the jump are concerns many of you have already had to take under consideration when planning your transition into full-time freelancer. Those of you who are freelancing as part of a pair may find my list especially applicable.

What About That House/Baby/Hot Tub We Were Saving Up For?

Since the beginning of time, my husband and I have been saving up for a house (we now live in a one-bedroom condo) so that I can start popping about babies (not too many!) without having to worry about space. While it’s been (very) slow going, we do have a small chunk of change socked away. When you’re part of a couple where either one or both of you is planning on going freelance, it’s only right that you have a discussion first about the major goals you share. If that leap is made, will it still be possible to save money for that house/Aeron desk chair/newborn? My own personal request: If we need to fall back on savings, our house savings do not qualify. As far as we are concerned, those savings DO NOT EXIST.

Where Does Our Bottom Line Lay?

For my first full year of freelancing, I was able to continue contributing to the bills as I always had. When I hit a rough patch (one I’m still struggling to get past), it was a given that Michael would pick up the slack, and be responsible for the lion’s share of our expenses. It made perfect sense: He was bringing in exponentially more than me, and though I felt guilty placing so much financial stress on him, you can’t bleed a stone (stone = me). Now, we need to take a closer look at our budget, and figure out our bottom line: How much do we need to be making — at the very least — in order to meet our monthly expenses.

What Will Happen If We Fail Miserably?

Since our savings account DOES NOT EXIST, we need to create a new savings account…one that contains at least six months’ worth of living expenses before he makes the leap. File this one under Things Stephanie Should Have Done Before She Left Her Corporate Job.

What About Our Health Insurance?

Michael likes to constantly remind me that I’m “not a survivor.” I have chronic sinus issues, chronic fatigue syndrome, issues with weak enamel, depression/anxiety…in short, I’m a bit of a wreck. While health insurance will be a bitch no matter what provider we decide to go with, we need to take special care to find a provider who can meet our specific (and extensive) needs. For example, I require good dental coverage, mental health coverage (I am crazy),  and good maternity benefits (so I can start spawning and stuff). Thank god for such great resources as Freelance Switch, AHIRC, eHealthInsurance, mediabistro, and Freelancers Union.

Will I Want to Kill You if You’re Around All Day?

This is, admittedly, a much smaller concern when compared to the ones above, but just as legitimate. While I dream of someday having my own office (with both door and lock), for now I have to rely on laptops, wireless headphones, compromise, and a whole lot of patience. Perhaps a talk about logistics is in order.

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What am I missing here? Freelance couples: What other issues have you come up against, and how have you dealt with them? Are there ways in which freelancing as part of a couple can make life more…awesome? Please share!

It’s inevitable. In the publishing world alone, both print and web publications are notorious for being late with freelancers’ paychecks. How can you deal with the vagaries of freelance income without allowing the stress to make your head implode?

Be Prepared:

While both troublesome and unprofessional, having to deal with delinquent clients is the nature of the beast, and it helps to be prepared for anything.

First of all, make sure you’re on top of both outgoing invoices and incoming paychecks, whether it takes an elaborate Excel spreadsheet or actual invoicing software (we’ll do a handy roundup of invoicing programs later this week). You should be well aware of whether or not certain clients have been tardy in their payments. Having a good system in place will aid in the eventual follow-ups you may need to do with certain clients, allowing you to reference invoice numbers and dates, project details, and amounts due.

Also, as I mentioned last week, you should avoid having all your eggs in one basket (continue marketing both to future and present clients!), and set up contingency accounts and the like.

Now What?

So. The inevitable has happened. You’ve had to visit the animal hospital four times in the past month — an expense you weren’t exactly expecting — the utilities bills are due, and you’re waiting on at least two checks that should have arrived already.

It’s time to check your budget and tighten your belt buckle. Are there expenses in your business plan that are more want than need…expenses that can be put off in favor of others as you track down your much-deserved paychecks? Perhaps you can put off purchasing a new printer in favor of paying rental costs for your office. Or maybe new business attire isn’t as necessary as you had first thought…at least not now. Your budget should list expenses in order of importance, making it easier on you during the more lean times to prioritize your spending.

It’s Time To Lay the Smack Down:

Now that you’ve made sure that all of your accounts are in order, it’s time to chase that check down. Lois Knight did a great post on this over at Freelance Folder. Basically, you should (initially) give you clients the benefit of the doubt. Is there a set time period on your invoices within which clients should pay you? This can be helpful in establishing accountability with your clients. If a reasonable amount of time has passed, send a “nudge.” And then another, if necessary, using a firm tone (this is your business, after all). If your naught client is still unresponsive, bring out the big guns. Consider small claims court, or file a grievance with the Better Business Bureau. Check out Knight’s post for more detailed information!

I hope that this post was helpful to you. Stay tuned for further information on effective invoicing practices.