In my experience, nothing stresses small business owners out quite like money does. 

Whether it's an awkward conversation about collecting past due payments, figuring out how to price your services, or just wondering how you'll pay the bills, money issues seem to make everyone's palms sweat. Throw in a personal relationship (friends, acquaintance, industry influencer) and it really can get messy. 

To take some of the stress out of these situations, here are a few thoughts for being a boss when it comes to friends and money. 

The Issue: A friend/acquaintance owes you money for work you've done. You don't want to ruffle feathers, but you need to get paid...yesterday.

These issues are tricky because you may have a personal relationship with the client, so sending an assertive email asking for money can feel awkward. You want to maintain your friendly vibe, but you can't afford not to get paid on time. Try this: 

• Sending a payment reminder email from a hello@ email address or from a accounting software system (like Freshbooks) instead of your personal business email. That gives the impression that the email could be from a VA or a bookkeeper, so you can take a more professional tone without worrying about hurting feelings. 
• Establish a late fee policy and add it to your invoices explaining that a fee will be charge if payment isn't received by X day. If a payment is late, you can reach out saying "Hey, just a reminder that your payment was due yesterday, but if you can pay today, I'll waive the late fee." That usually gets people to take action! And if not, tack on that late fee.

The Issue: A friend wants to work with you/buy your stuff but you can't give out "friend discounts" all the time. How do you handle it? 

These situations are tricky because you probably haven't made decisions about how you'll handle certain things and you don't have systems to back them up. So you're shooting from the hip every time. Once you have a few decisions made about your client workflows, you'll be able to thank them for being interested, and then direct them to the first step in your process. You can say something about how you're working on being more organized in your business, so they'll "just need to do ____ to work with you/book an appointment/buy your thing." For example: 

• An artist might send clients a link to a commissioned artwork form (which includes information about what they want, their budget, etc.), instead of going back and forth via text for a week.
• A massage therapist might send them a link to a scheduling app that requires payment in order to schedule (like Acuity), instead of having to deal with asking a friend for payment at the end of the appointment. 
• A designer might send an email that has a link for the client to make a X% deposit "to hold your spot," instead of waiting weeks after the project is done to finally get paid. 

It says to both parties that this is a legit business and formalizes the relationship. There's no decision to be made about how you'll handle this particular situation because you have a process and systems that support it! It's just how you run your business.

Technology is a beautiful thing for these sorts of issues. Utilize and implement wherever you can.

The Issue: Anytime someone you know wants to hire you, you feel awkward about your rates and always lower them on the spot...but regret it later. 

Who has done this before? Yep, thought so. Most business owners I know have at some point or another!

The best way to address this issue is by: 

• Put prices on your stuff (service providers, I'm talking to you). There's a trend for people to just put a link to "schedule a consultation" on their website instead of showing the price of something. The idea being that you want to get them on the phone to "sell 'em" before revealing the price...and this always makes for a super uncomfortable conversation for strangers, but with friends it inevitably ends with you dropping your rates. So, create a price sheet or put prices on your website so that you have to stick with your prices. For some reason having something in print makes it seem non-negotiable. Plus, they'll know ahead of time what sort of budget to expect. 

• Owning it. Take a deep breath and realize that if you're not looking out for you, no one else will. You have something to offer that someone else values. You exchange value (item/service) for value (money). The end. No deals needed.