I have trouble asking to be paid

I have run a small web hosting and design business for over 18 years with some friends. We’re not big but we have provided a solid and reliable service for a long time and we have a number of great clients. We provide a reliable, friendly and fairly priced service, I’m really quite proud of what we do.

twohandscashbig-040614However, we’ve never been aggressive or strict about billing with our clients. We let our billing software send automated e-mail reminders and occasionally we send a personal note politely saying ‘Hey you know you’re really overdue on your bill’. We never shut people off for being past due. I just assume they must just have other things going on and this was a low priority bill. This results in some clients being months, sometimes years behind in payment. (yes, seriously, years)

I guess, while my logical side knows better and knows some people will take advantage of trusting people like me, I still believe the best in everyone and assume everyone intends to pay and that hard work will be recognized and rewarded fairly.

Sometimes this had paid off, the person who moved and changed e-mail addresses and totally forgot they owed us money for their website finally resurfaces athen says ‘Oh I’m really sorry, I’ll pay my entire balance right now, thank you so much for not shutting it off‘. However for everyone of those clients there are 2 or 3 others that say, ‘I no longer want this site please cancel it and void any old invoices‘. Sigh, there goes months of services rendered with no compensation. I could argue with these people that they should have informed us earlier and that since we kept their site up they owe us, but is it worth arguing?

Asking for money isn’t a strong suit of mine, to say the least. In fact I joke with friends I do contract work with that they need to keep an eye on me because I am amazingly adept at NOT making money. Given the chance I give away, not only the milk, but the entire cow.

I feel greedy, guilty and selfish asking people to pay me for work I’ve done or services I’ve provided, like I’m being unkind to them by even asking. A real friend/nice person wouldn’t ask. I’ve lost count of how many times I’ve felt bad about asking for money for work I’ve done on a website, and thus never even billed them for my time at all. I rationalize this for various reasons like;


  • “It was just a few minutes/hours of work, not really worth bothering them with.”

  • “I know they don’t have much money, I hate to bug them about this.”

  • “They are a non-profit I like, this’ll just be my donation.”

  • “It wasn’t their fault their (dreadfully neglected) wordpress site got hacked, I hate to bill them to fix it”

  • “They are a friend, this will just be a favor for them. I’m sure they’ll return in kind when/if the time comes.”

  • “It will take more time explaining what I did and why I want to charge for it than it’s worth.”

  • “They already pay me for hosting their site, I’ll just consider this part of the services we offer for hosting”

I also tend to really round down my costs

  • high-risk-payments-150x150Well I worked 5 hours on this, but they probably only expected 2 so I’ll just bill that”.

  • “They only asked me to update the graphics, they didn’t know the site was out of date and needed 2 hours of other work, so I’ll just bill what they expected.”

This has been an ongoing thing for pretty much the life of the business and something I’ve struggled with all along. The first step to recovery is accepting you have a problem right? “Hi, my name is Matt, and I have a problem asking for money.”

… but recently the ‘universe’ spoke on this issue. Coincedence? kismet? karma? who knows.. but a few weeks ago in a period of several hours the following messages hit me;

1) Grace Judson, a friend I’ve never met in person but met online because our websites were both based off the word Svaha, recently posted a link to this blog & video on Facebook; How to get paid when you hate asking for money .

In fact, much of the first part of this post I wrote as a comment on her facebook entry with that post.

It was rather ironic that she posted this (and I took note of it) since I had moved her over to my server a while ago but didn’t add her to our billing system for a number of months because I wanted to make sure she was happy with our service before I billed. She asked me on numerous occasions to bill her before I finally did.

The video itself has some good advice, mainly that people should be confident about their services and their value. Perhaps that’s part of the root of my money issues in that while I believe the services we offer and the work I do is worth the amount I charge, I lack the self-confidence to argue this. If a client were ever to say “$75/hour? No way, I don’t feel you’re worth that much, I’ll pay $20”, I probably wouldn’t argue with them (though I certainly would never do business with them again). In fact, something like this happened to me last year

To be fair, business savvy friends like Nicole at Breaking Even Communications have been giving me business advice and telling me that things need to change for a long time, so the above examples are just the ‘final straws’ that pushed me into working towards a solution.

I had written up some ideas of what I’m going to do to address the above problems, but again the universe spoke and computer entropy (yes it happens to geeks too, more often than we care to admit. shh) struck and I lost the rest of this post. I guess that was a message that if I wrote too much more this post would way exceed even the most dedicated TL;DR (too long; didn’t read) threshholds.

So stay tuned for the follow up post… and if you don’t see one soon bug me, this is important.

I’ll end with a song that always comes to mind when I’m thinking about money. I want a new religion.

Inbox Zero – A never ending battle

I mentioned a few days ago that one of my goals is to get more organized and that one of the things I’m trying to do is Inbox Zero. This is really a pretty simple concept, your inbox should be for incoming e-mail only and should be empty when you’re done. Your goal is to take each message and either;

  1. Trash it
  2. Archive it in an ARCHIVE folder
  3. Reply to it & then archive it
  4. If it’s a message you need to save and reference quickly for a little bit, like an online receipt, plane reservation etc then move it to a HOLD folder
  5. If you don’t have time to reply, but you need to, move it to a FOLLOWUP folder.
  6. Put newsletters/blog entries you want to read later in a REAMDE folder  Ok I admit it, I cheated with this, this isn’t an official “Zero Inbox” folder and I’m sure Merlin Mann would scold me. However, there are messages I want to read more thoroughly some day but I don’t have time to read right now, so I made a ‘README’ folder. This is admittedly just another archive since I rarely read anything in there, but it helped me get it out of my inbox so… don’t judge me)

I’m sure some people are wondering why I’m making this seem like a big deal. Realize that I use e-mail for communications not just with friends & family but also for many work related needs, so I literally get several hundered messages each day. Seriously.

So… I’ve gotten really good at emptying my inbox. Part of this is just diligence that it’s a routine I’m used to. Part of this is actually unsubscribing from mailing lists I never read or from e-mail newsletters/ads from businesses I don’t care that much about.

A few mantras I repeat to myself as I’m sorting my e-mail;

  • I am not the internet archive – I am a admittedly a digital packrat, I tend to save way too much e-mail. Part of this involved me saving messages to mailing lists I’m on cause I or others might need to reference an old post someday. So I had to force myself to remember ;
    • The lists are archived elsewhere
    • It’s not my job to save this, no one else is expecting me too
    • I’m wasting my time/space saving something I’ll likely never need
    • … oh AND the messages weren’t really that important anyways
  • I have more important things to do – For messages that have a subject I’m only kind of interested in, I need to remember I have a to-do list of more important things to do than read messages that aren’t immediately relevant. There is no quiz later proving I read each and every message that came into my mailbox. If it’s not a personal message, odds are there’s little or nothing in it I care about. If I really think I should read it later I put it in my README folder.
  • I can find it later – This is for messages archive. If it’s a message I feel I should save for later, for whatever reason, part of what helps me get this out of my inbox is that I remind myself ‘I can find this later if I need it’.
  • Trash is a 30 day archive – My trash is set to auto-delete any messages after 30 days. Therefore, for things like logs and such where I may need to reference them soon but not save them forever, I remind myself ‘Well, I can always find it in my trash folder if I need it’. I feel a bit of a hypocrit saying this since I have, on several occasions in my previous job, lectured people that they shouldn’t keep important documents in their trash folder etc (seriously, people did this) so I remind myself before I ever do this ‘This document isn’t that important anyways, even if it was lost’

So as I’ve mentioned I’ve gotten pretty good at trimming down my inbox, but now I’ve got way too much stuff in my ‘followup’ folder, and it’s a little scary to go look in there cause unlike my previous inbox, everything in my followup folder really needs my time & attention. It’s like walking into a crowded room of people who need to talk to you (yikes, that’s a scary visual for me). I’m still figuring out plans on how to deal with organizing and ‘zero’-ing this mailbox, what I’ve come up with so far is;

  • If it’s a bigger task, add it to my Asana.com to-do list. Yes, this is like moving it to yet another folder, I know, but by promoting to this level I’m acknowledging it’s really a priority and I can rank it in comparison to other tasks. I can also invite others to this project if it’s something bigger than just me.
  • Schedule It – I haven’t done this much yet, but I know it’s the next step. Actually setting aside time for a task to get it done.
  • For e-mail replies, I need to remember ‘Brevity is the soul of wit’, or perhaps K.I.S.S (Keep it Simple Stupid), I don’t need to write an essay, a few short sentances is probably enough. If an e-mail really requires an essay response then it’s probably a project that should be prioritized and possibly scheduled.

I’ll let you know when/if my followup folder gets organized. I’ll put ‘write a followup blog entry’ on my to do list right now 🙂

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