Freelance Matters

When to Quit.

May 23, 2012


It’s been almost 2 years since I left my dream job as senior art director at my old advertising agency – but I can still taste the anxiety that decision left me with.

So when Ramona, an aspiring creative entrepreneur, emailed me for advice about leaving her current job for another job that is a bit more of a creative challenge it was a no-brainer that she should do it – but I know first hand how much emotion can cloud your perception when it comes to weighing the pros and cons to make such a bold decision.

I want to share with you all my email correspondence with Ramona where I help her break it down. Even though Ramona’s circumstances are specific (and those specifics should be considered even when following your heart) I think it could potentially help a few of you who are struggling with the decision of when to quit too.

From Ramona:
Subject: Taking the risk to following your dreams or staying safe???

Dear Kathleen,
I have been reading your blog for quite a while now and you truly inspire me when it comes to starting your own business, following your dreams and the such. I am writing your today for advice as I find myself in a situation where I have to make a pretty tough decision.

So here’s my story: I graduated from university in 2009 with a degree in International Business Management. I have been working as an assistant for the CEO ever since in a small company doing regional development and marketing.

At first I was challenged, had my own projects and was able to grow. But now I am bored most of the time. Yes I get a good paycheck at the end of the month, but I do not accomplish anything – I have to add that I am the kind of person who needs the challenge. I always want to grow and move forward. If I’m really in it, busy (in a good way) and challenged I become really creative and I work harder than anything. But I haven’t experienced this in a long time. I have of course applied for new jobs in communication, marketing, events but so far nothing has worked out so far.
My dream has always been to be a freelance one day doing creative consulting and events and weddings and maybe development help in 3rd world countries.

I know my time to be a freelance has not come yet. But… here’s the thing. I go to a church here and they opened up a public restaurant/café last October. It’s seriously a great restaurant and one that’s offering foods that do not exist in this region where I live yet. It’s very stylish and always displays local artists and it’s cozy and the food is truly great! Sadly, it’s not running the way it should be yet due to lack of leadership from the manager. Last week the owners sat down with me and offered me the position as restaurant manager. They told me that they believe that I can manage and lead people, that I would bring a heart and a vision and creativity in it that could turn this thing around and make it to the place it could be.

Wow… I was pretty overwhelmed and honored and scared I guess. I have no experience whatsoever with leading a restaurant. Like nothing. Plus, I would for now get less money than I do now and my time schedule and everything in my life would change.

If I’m honest with you I have always looked up to women who followed their dreams no matter what. Who got out of their comfort zone and just did it. They were passionate and made it happen. I’ve always wanted to be that kind of a woman. I do believe that if I take on this job it would be one step further to being a freelance one day as I would learn how to run a business. It would be great challenge and a great risk. Yes, running a restaurant sounds fancy and I often romanticize everything in my life and dream a fairy tale. I do know it would be hard work and busy schedules. I just really want to accomplish something in my life. Not for the money or for fame, but for myself.Isn’t now the time to be risky and go after my dreams and just get out there and do it? Follow my heart and dream?

I know I am totally writing you all this personal stuff and I don’t even know you but I wanted to ask you because you seem to be the person who did it and you know how much work it is. Do all my thoughts make sense to you? Do I sound a little weird just telling you all this?



My former life as senior art director at a really rad ad agency – it was a tough decision to leave. Photo by David McNeese.

Here’s my repsonse to Ramona’s dilemma:

Hi Ramona!
First off, I’m really flattered that you thought of me as someone to come to for advice. It really means a lot! I don’t have all the answers but I have been in the position of making hard career decisions – so I would love to share my point of view on it all.
Reading through your email it seems as if your main hesitations to jump ship come from: A) Money, B) Lack of Experience, and C) Fear of Change. I would like to address each of these and break it down so hopefully it’s a little less scary. 
I’m going to start with Fear of Change because this is the one I know best. I remember very clearly when I was thinking about leaving my ad agency job to go freelance that I was most terrified of making the wrong decision and stepping into the unknown. I was fraught with anxiety that I was killing my career and for what? In hindsight, I am clear that there is no such thing as a right or wrong decision. If you insist on moving forward in life you won’t ever make a wrong decision – because it just doesn’t exist – but only if you use every experience as an opportunity to learn. Making a decision at all (and then actually executing on it) is the hard part. 
I think a nine-to-five job with a steady paycheck provides us with a certain amount of security but the truth is things can always change at a moment’s notice. Consider this: what if your boss was planning on closing up shop or letting you go tomorrow what would you do? You would probably consider it a blessing and take the job at the restaurant. The only difference is that someone else made the decision for you. Be brave enough to make your own decisions
Along with being afraid of change – I was also terrified of the unknown. Here I was feeling like a spoiled brat because I was leaving my dream job for uncharted territory. I felt inexperienced and had no concrete picture of what freelancing would look like – and that was scary. This turned out to be a blessing because it meant I could decide for myself what that would look like. I think the same will go for you. You will be able to manage this restaurant the way you see it. Because you have no experience you may bring a certain amount of creativity and individuality to the job that no one else could. My advice is to be transparent and honest in this process. Authenticity will bring people who want to help you succeed to the forefront. 
And here’s another secret I’ve learned in life: Beyond a little bit of training and education, EVERYONE is making it up. Nobody is born a business owner or manager or killer designer. You’ll figure it out as you go – and that’s the beauty of it. 
While I’m a huge advocate for creative entrepreneurs doing their thing I’m always hesitant to tell anyone to quit their nine-to-five (before they’re ready) because of the money issue. Nothing kills creativity like not being able to pay your bills. That’s just the truth of it. But in your situation at least you’ll still be making a steady paycheck – just a little less than you’re used to. However, it sounds like the trade-off could be worth it. I think as long as you can still pay your bills the money issue isn’t much of an issue, for now. 
Obviously, you can ask your employers for a raise as you bring some life (and organization) back into the restaurant. But more importantly, if your end goal is to work for yourself, I would consider how your new role as a restaurant manager is adding to your expertise as a creative consultant and event planner. I would also think about how you could begin to build your business on the side. Put together a portfolio of weddings & events you did for friends and start charging for your services (even if it’s just a little bit at first). You’ll feel that much more confident when you finally make that leap as well. 
It sounds like, for you, the decision has already been made. Quit your job and follow your heart. I say romanticize the restaurant and hang on to that fantasy – that’s what will make you a successful (and happy) manager even when things are tough. And know that this decision isn’t permanent – when it’s time to move on again you’ll move on.


What do you guys think? What advice would you give to someone in Ramona’s position?

Freelance Matters | How to work with a printer

February 28, 2012


I get emails asking about the printing process and finding a great printer more than anything. So, in this post I’m going to tell you how to find (and develop a relationship with) a great printer. In an era where everything is cheap, fast, digital & online developing vendor relationships is somewhat of a lost art. But it’s important. Especially if you want to be a print designer.

One of my favorite printers, Julie Harman from Heritage, started working with me 6 years ago as a newbie who knew nothing about printing (they don’t teach you this stuff in design school!). She gently guided me through the print process and to this day I give her loads of credit when it comes to my success as a print designer. I actually interviewed her to get some insight for this post and she gave me lots of tips and pointers that I’m eager to share with you.




I first started working with my printers 6 years ago when I got my job at a small ad agency. I was lucky in that they were vying for my business – but if you’re a small freelance designer you’re going to have to go out and find someone willing to work with you.

• Ask a friend, teacher or mentor for a recommendation.
• When you contact a printer be sure to name drop whoever recommended you.
• Be honest about your experience – let your printer know if you need guidance through your first print job.
• Be willing (and eager) to learn – My printer Julie is willing to invest her time in designers who are open to learning about the process.
• Julie says: “A good printer is one that will ask you questions – things like ‘What are you going to do with this project? Who is going to be viewing this?'”

Ask your printer for a tour. This will help you understand the life of a print job from beginning to finish. There is a big difference between a digital vs. a 2-color letterpress job – seeing it in action will help you understand the costs involved.

I have a handful of printers I work with. One does letterpress while another does great (and inexpensive) digital jobs. I have my go-to when it comes to small 2-color offset lithography jobs and another for large-format jobs. Different printers will have strengths in different areas. I’ve been using the same handful of printers for years.

I would like to mention here that the only online printer I ever use is MOO for business cards from time-to-time. They have great customer service and a quality product.

Otherwise, I use local businesses and I’m loyal to the printers I utilize. It might cost a little more but it’s well worth it to know I’ve got real people doing their best to make my jobs look great on paper. These relationships have paid off big time over the years.



I’ve been obsessed with paper since college. I remember going to the Neenah site and requesting free samples while still in college. Over the past 7 years I’ve learned which stocks are the best for digital, offset and letterpress. I’ve had very expensive, hard to find paper over-nighted from Germany, and I’ve used scraps leftover for smaller budget jobs. In fact, my own business cards are printed on chipboard scraps my printer found between reams of paper out on the press floor.

My point is that learning about paper is an ongoing process. When you get a tour from your printer be sure to ask about paper. They’ll explain the difference between coated, matte and uncalendered stocks. And if you ask nicely they may give you a couple swatch books for reference (be sure to ask them how to read the swatch books too).

When I asked my printer Julie the #1 thing a designer can do to make a job go smoothly from start to finish she had 2 words: print specs. The best thing you can do to make a run without a hitch is give your printer as much information as possible. I do this by providing print specifications. Here’s an example of my print specs.


You’ll want to tell you printer:
1. A job description
2. Quantities
3. Final trim size (folded and flat)
4. Printing (letterpress, digital, offset) – You’ll notice here that I say “4/4” this means it is four color process and double-sided. So if I say 2/0 that means two-color, single-sided.
5. Paper – specify paper. Sometimes here I’ll give a couple options and my printer knows to pick the one that is easier to get or most cost-friendly.
6. Any other special notes (like die cuts, assembly information, etc.)
7. Proofing information – do you need a printed mock-up or will a PDF work just fine?
8. Deadline
9. Final delivery information – is it going to you or directly to the client?

You might even include little diagrams if your job is particularly tricky or involved.

Printing is not cheap but a great printer will help you find alternatives to cut down costs. When you’re on a budget something usually has to give – either the print method (you may have to go with a 2-color litho job instead of letterpress) or paper (which can account for about 1/3 of the cost when it comes to printing).

When you request an estimate from your printer you will need to provide them with print specs. Be sure to request a few different quantities – the more you print the better price break you get – this is due to minimum paper orders and set up fees. So sometimes a 500 piece job will only be dollars less than printing 750 or 1,000.

If your estimate comes back too high ask your printer for creative ways to get it down – it may mean using a different print method or paper stock.

NOTE: When you share your quote with your client be sure to account for tax. Also, it is standard for designers to mark up printing 10% – 25% to cover coordination costs. Handling printing is a service that you should be compensated for.

• No job will ever be perfect. There will always be minor flaws in every print job – embrace it as part of the beauty of a medium like print.
• Learn the difference between digital, offset and letterpress.
• Learn how to set up your print files. Ask your printer for a tutorial on the best way to package your files or export your PDF for printing.
• For custom letterpress jobs or huge expensive jobs you might request to be there for a press check to make sure all the photos, embossing and colors are coming out properly.
• I like to give my printers 2 weeks average to complete a job. Sometimes certain jobs will take longer if they require special binding or letterpressing. And if I’m in a bind or a job is digital they are usually completed in about 1 week.

If you have any additional print questions ask in the comments and I’ll do my best to answer!

• Freelance Matters | Estimating & Billing
• The time I cried at the printer
• Best in Print

Home Sweet Home Office

February 1, 2012











I mentioned a while back that I was trading my master bedroom with my home office in order to have more space for not only my sister and myself but for our new employee. (!!!)

While I was away at Alt Summit Jeremy and my sister, Tara, completely set up the new office with plants, a new light fixture and an organizational overhaul. As Tara was going through my desk drawers and sorting through old boxes in the closet she found my diary from 1991 in which I describe what I want to be wearing at my own funeral. I’m giving my 9 year old self a big hug right now. But in the event that I die anytime soon please, dear readers, make sure my family knows that I want all my boots (including Mister Scooty Boots) to go with me. Like a Pharoah who takes her belongings with her to her tomb.

Enough of that depressing chatter. Back to the office! It’s so bright and airy and perfect. We considered renting a space for a while (to feel more legit) but nothing quite compared to my home. So we hired a legitimate employee instead. We’re all in the same space, our office feels like an office and work feels like work. And if Jeff Lewis can run a business and make millions from his living room so can we.

Oh and remember the DIY desks I tried to make? I ended up painting them with chalkboard paint and throwing them on the wall instead. Now they serve as a calendar board and client / project list. We ended up buying two large, sturdy dining room tables to create one big work space for all of us to sit at. So maybe I don’t hate DIY afterall.

What do you think about the new space? Do you work from home too?

• A Switcheroo
• My old home office
• New master bedroom sneak peek

Freelance Matters | When To Work For Free

January 4, 2012


I’ve addressed how to estimate and bill freelance projects. I’ve talked about the importance of getting paid for your work – because if you don’t value your work, monetarily, neither will anyone else. But today I want to talk about when you SHOULD work for free. I get asked by other freelancers all the time about how I deal with “pro-bono” projects.

So here it goes.

Point 1. The only time you should work for “free” is when you can see the value of what you have to gain from the experience.

Here are a few instances where this value might be recognized:

• When you need to build your portfolio: If you’re new to your creative endeavor and are building experience it might be worthwhile to work for free (or a very small charge). But if you do this – you better make SURE that project becomes portfolio worthy. Make it clear to your client that in exchange for your service you want them to trust your creative vision and guidance so that you end up with a piece you’re proud to show off.

• When you work for trade: I love working for trade and never consider it “free”. I like to view trade as an exchange of energy – so it’s wise to make sure both parties understand the worth of the services or products being traded so it’s a fair deal. It should be obvious but needs to be said: I will not work for trade if the other party doesn’t have services or products of value to me.

• Working for charity: I’ve been asked to do pro-bono work for charities work a lot. I only say yes when the charity asking is meaningful to me – I get value from feeling like I was able to contribute to a good cause. If you accept pro-bono work and become resentful about it only creates bad karma for you and them. You do not have to say yes to every charity that comes knocking at your door just because they’re a charity.

• You owe someone a favor: I’ve been blessed with lots of generosity from friends within my industry. Vendors and other experts who have gifted me with knowledge and goods. When they ask for a design favor I happily return it.

• Working for friends & family:
This one is probably the trickiest. When it comes to wedding invitations or baby announcements I almost always say yes (or offer before they even ask) if I have the time. It’s hard to say “no” to family & friends but the times I do they always seem to understand.

And that brings us to point #2.


Point 2. – Always make sure whoever is receiving your services for free knows what your worth in dollar value.

This might mean sending your charity or friend an invoice with the dollar amount of your services – but with a $0 balance at the bottom. You might even include a note saying “Happy Birthday!” even if it’s nowhere near their birthday. This way they know it’s kind of a special, rare thing that you’re not willing to do all the time. (But don’t do this if it really is a birthday / wedding / baby gift – that would be awkward).

I just want to leave you with one final thought when it comes to working for free and saying “no.” If someone loves your work and services and wants to hire you but doesn’t have the money to pay for your services then they are probably not a good fit for you. Just because they really like you and you really like your job doesn’t mean you have to work for them for free.

What’s your stance on working for free? Do you have a hard time saying no? When do you say yes?

P.S. I love Jessica Hische’s Should I Work For Free flowchart.

Freelance Matters | Why I Quit Working With Brides

November 3, 2011


I quit designing wedding invitations because the wedding industry is whack and brides (no matter how cool) always go a little crazy when planning a wedding.

The end.

Okay. That’s not entirely true. Let me start from the beginning with how & why I started designing wedding invitations.


It started when I designed my own wedding invitations. I really wasn’t planning on designing them. I told Jeremy we would send out a letter to our nearest and dearest and call it a day. Well, I’m a designer and can’t not design anything I’m creating. The invites grabbed the attention of Joanna Goddard (of A Cup of Joe) – she posted them to her blog and the world noticed. I started getting emails from brides-to-be asking if I could design their invitations. Meanwhile, I was working as a full time senior art director at an advertising agency – I was designing campaigns for the NBA Hornets, cable providers and credit unions. Designing wedding invitations on the side seemed like a fun creative release.

What I loved about designing wedding invitations is that I wasn’t using my skills to sell something that I didn’t really care about and there was a unique & real love story to tell in each design. I kept getting brides from all over the country and even overseas asking me to design their invites. Then it came to the point where designing invitations on the side became a part-time job. I was starting to feel like I was done with advertising and Jeremy encouraged me to try my own thing. I quit my job and within a year of freelancing I made almost as much as I was at my ad job. A large portion of that income was coming from designing wedding invitations.

As my time became more in demand my prices went up. Now some brides were willing to pay more for their invitations than I paid for my entire wedding. I found the more a client paid for their invitation the crazier they were. Planning a wedding can take it’s toll on anyone – no matter how laid back they claim to be.

9 times out of 10 I was sending out custom estimates (which take time to put together) to brides who had NO IDEA that people were spending THOUSANDS of dollars on invitations and wanted me to custom design & letterpress theirs for pennies. I would get these harsh emails about being “way too expensive.” I don’t blame them but at the same time it hurt my feelings. Around this same time I was finding designs – very similar to my own and not designed by me – all over the internet. Which is a whole other Freelance Matters topic.

It was easy to become resentful and bitter. And as we all know – this is not good for the soul.

I also found that even as I was gaining popularity (yay! business!) as a custom invitation designer I hated only being known for designing invitations. People started asking me about wedding etiquette and were asking me to design seating charts and place cards and you guys – I didn’t even know such things existed. I had no idea there was a proper order of events… I mean, Jeremy and I were married by a sideshow performer. I was constantly clarifying that I am a designer and art director than happens to be known for designing wedding invitations.

Okay. I know you guys really want me to dish some dirt on the couple that pushed me over the edge. It’s really not so bad but here’s how it happened: One evening I got an email from a dysfunctional bride telling me that her rehearsal dinner went to shit and that it was all my fault because of the place cards I had designed for her. The groom asked me what I was going to do to rectify the situation. I double-checked my files and found no fault of my own. But I was still terribly upset that their rehearsal dinner sucked and that they thought it was all my fault. I refunded some of their money and put a note up on my rates page saying that I was no longer accepting wedding invitation clients. Done. But I was ready to move on – this was just the last straw that pushed me into action. So really, I’d like to thank that couple.

I should tell you guys now that 99% of the brides I worked with were amazing – every single one featured on J&K has been nothing short of perfect.

Any time I got a request from a groom I knew the job would be a disaster. Grooms are contacting me because A) The bride doesn’t really care of about the invitation and has passed this duty off to the groom (and guys seem to like my style) or B) Because the groom actually cares wedding invitations. Either way, they were always a little out of their mind. Not bad. Just a tad crazy. I’m telling you – the wedding industry demands a certain kind of perfection and breeds a certain kind of insanity that just doesn’t jive with my work style.

At the same time, I was really getting into branding for small businesses. I felt like I was making a difference for artistpreneurs and microbusinesses – I was giving “the little guys” confidence to help grow their business and the look & feel to match. Branding seemed to be a lot less disposable but still just as personal as wedding invitations. I became passionate about talking about freelancing and giving other creatives advice for moving forward in their careers too.

I have worked for some really amazing brides but not a single day goes by that I regret my decision to stop designing wedding invitations. But I’m also still asked by many couples for estimates. I send them to the following:
• Check out the designer rolodex and sponsors at Oh So Beautiful Paper – they’re all amazing. And a huge thanks to Nole who always supported me and shared my work with the world.
• The sponsors at A Practical Wedding (the best site out there for the bride who doesn’t want to lose her shit planning a wedding) are really great too.
• My friend Rachel at Pencil Shavings has a really rad style – and she does much more than just wedding invites!

So that’s the story of how I began working with – and then quit working with brides. And grooms. I don’t regret the work I did and I actually still have a couple more invitations to share with you all soon. Invitation design served me well and taught me lots of lessons – but I’m excited to move on to the next chapter of my career.

Do any of you design wedding invitations – either for a living or on the side? What has your experience been like? Are any of you wanting to break into the invite design business? Let’s chat in the comments.

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