25 life lessons from 25 years in business

Twenty-five years ago today I made one of the scariest (and best) decisions of my life. I had a three-month old baby and one (count ‘em—one) freelance client who paid me a few hundred dollars a month. Oh, and a husband who fully believed I could do it—can’t overlook that. So I left my job ...

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Twenty-five years ago today I made one of the scariest (and best) decisions of my life. I had a three-month old baby and one (count ‘em—one) freelance client who paid me a few hundred dollars a month. Oh, and a husband who fully believed I could do it—can’t overlook that. So I left my job as an art director at an Indianapolis ad agency to start my own graphic design business. I designed logos with a sleeping baby in my arms. I formatted newsletters with one hand while wiping off pacifiers with the other. I closed doors and hunched around the telephone receiver so the client couldn’t hear the screaming toddler in the other room. I worked all day. I worked all night sometimes. I stressed about money (sometimes it poured in, other times it was several months late, and although my husband worked we also needed my income to make ends meet). I took my daughter to a babysitter two or three days a week so I could attend meetings and get some work done. But I made it work.

Then I had another daughter less than three years later. When she was born, I had my computer set up in the living room so I could keep an eye on both girls while I tried to get something done. I hired my sister to help for a while, answering phone calls and getting project estimates and doing my billing. I experimented with moving my office outside my home, thinking I would find separation between work and life. I didn’t. So I moved back home—and had my third child, a son.

Throughout these 25 years, I’ve kept on working. Through crazy levels of work and a variety of clients and sometimes virtually no work but almost always there was plenty to keep me as busy as I wanted to be. I started writing books (and the occasional copywriting project), but I kept on designing. I designed and sold sterling silver jewelry for a while. Once my first book was published, I developed what some would call a ministry of my own, and I did that stuff, too—some speaking, building a social media presence, and so on. I’ve attended writing conferences and retreats, but through it all, I’ve kept my business going. I’m fortunate because, for me, it all feels related. It’s all about creativity—in design, in writing (in whatever form), in prayer. Rather than keep all the pieces separate and distinct, I was able to merge it all into one. My thinking was this: it all comes from the same place, from the same skill set, and it’s too complicated to have multiple businesses. So whatever I do in the “creative” realm falls under the umbrella of my business. Some parts of it earn money, some don’t, but I do it all anyway.

One year ago, with two of my kids on their own now and my youngest in high school, I moved my office again—into the building that served as my dad’s art studio until he died. I love being in that space, and I’ve finally found a decent work-life balance. Over the years, I’ve learned plenty, and although many of these lessons are specific to me and the industry I work in, many of them apply across the board. So in celebration of 25 years of building my own life, I wanted to share 25 lessons I’ve learned, in no particular order.

  1. Don’t try to be something you’re not. Embrace who you are. Be real. Don’t exaggerate or puff yourself up. Authenticity makes up for a lot of other flaws. If you work at home, say so. Most people are jealous that you get to work from home, or that you’re able to set your own hours, or what have you.
  2. You’re in charge of “marketing” yourself. Figure out how you want to be known before people ask. “I own my own graphic design business, and I work from home.” For me it was important to establish that—not because it made me any less professional, but because my way of working was affected by my being at home. A client might hear my kids in the background. They might call while I’m at the grocery. But on the flip side, they also might send me a big project at 5 pm and have it waiting for them the next morning because I sometimes work crazy hours.
  3. Just because you’re self-employed doesn’t mean you’re less of a professional. Don’t act like it or be embarrassed. Working from home, working for yourself, is a legit way to do it.
  4. Put on makeup. Get dressed. Put on shoes. Go “in” to the office. Many people who work from home love the fact that they don’t have to do these things, but honestly, when I don’t, I feel unprofessional. When I get ready for the day, I feel like I’m on equal footing with the client… especially now that some of my clients like video calling.
  5. You don’t have to apologize when asking for payment. You earned it. The client agreed to it. It’s yours, so don’t be embarrassed to remind them when the payment is late. You don’t owe them reasons why you need the money—that isn’t any of their business. But getting paid is a crucial part of being in business, and they have to understand that.
  6. Just because you work from home or have a flexible schedule, you are not obligated to “volunteer” for anything and everything. If you want to volunteer, having a flexible schedule is one of the perks, so go for it. But if you don’t, don’t accept any perceived pressure from others about it.
  7. If you do want to volunteer, find ways to volunteer that tie in to your particular skill set. For instance, I don’t volunteer to chaperone groups of teenagers or work behind the scenes at a production my kids are in—but you need a t-shirt or an ad or a program designed? I’m your girl. These are legitimate ways to contribute, and they come with the added benefit of being able to do them on your own time.
  8. Sometimes you should ask questions, not because you don’t know, but because other people need the chance to weigh in and be the “experts.” Offer people the gift of not always being on the receiving end of your expertise.
  9. This business isn’t life and death. Some things are—but not this ad deadline or whether the layout is emailed to the client on Thursday or Friday. That’s not to say deadlines aren’t important. Part of succeeding in business is living up to your promises. But don’t get caught up in unnecessary drama because when a real life or death situation happens (you have to have your dad flown home from Florida because they just discovered the cancer is everywhere and he doesn’t have much time, for instance), you realize how non-crucial the other things are. They may be important, but they’re not the most important things.
  10. Don’t give away your work for free, unless you specifically want to. Maybe you believe in a cause and want to help. Great. But non-profits still earn money and can pay for services they need. And someone else’s charity or ministry does not have to become your own. You have bills to pay, and you are offering a professional service. When you let yourself do too many things for free (or discounted rates), you will become resentful.
  11. Sometimes, even when you want to help someone with a lower rate or no rate, you should still let them pay you. Yes, people appreciate cost savings, but if they’re not paying you, you may not be as diligent about deadlines or details. There are times when I insist on paying someone else more than they asked because I need to be able to know they’ll take the job seriously. Because free or not, it’s still important to me.
  12. When you hire someone to do sub-contracted work for you, ultimately you’re responsible if they do not come through. Prepare for that. Allow extra time in the schedule. But you don’t have to be a martyr and do everything yourself because no one else delivers at the same level as you do. If you need help, get it. And try to learn how to better direct others to give you what you need.
  13. Actually, in general, be prepared to accept responsibility. For success as well as failure. Don’t play the blame game. If you screw up, admit it and apologize. If it’s not your fault completely, own your role in it. Maybe it will cost you a client, but alternatively, it might earn you greater respect. Whatever happens, though, at least you’ll know you handled it well.
  14. If there are professional services you can hire out, do it. If you can afford it (even if it’s a stretch), let someone else—who is better and more efficient—do things to help. It’s not failure to “farm out” accounting or invoicing or cleaning or computer work. If it makes your schedule more manageable, or if it’s something you don’t know how to do (or don’t want to), don’t hesitate to get help.
  15. Don’t always let other people decide for you. Part of the reason you work for yourself is so you can make choices about your work conditions and quality of life—who you work for, what projects you accept, and what tasks you will do. So don’t hold on to clients way too long simply because you want the money. Or if you do, don’t blame the client. Acknowledge to yourself that you’ve made the choice to go through all of it because you want the income, then don’t waste energy being upset about how the client does things.
  16. Pray about it, whatever “it” is—whether to accept a new client, go in a different direction, end a long-term business relationship, move offices, put together a project estimate, whatever. I don’t always do this, and I don’t always stop in a busy day to remember to ask God if a particular situation is one I want to be in. But when I do, when I take that time to say, “God, ultimately, this business is yours. My talents come from you. My life is at your pleasure,” those are the times when God clearly directs me and helps me make the best choices.
  17. There’s no sense in trying to keep your spiritual life separate from your business life, because you are a spiritual person and your beliefs inform your morals, your work ethic, and how you treat people. Use wisdom and don’t talk about faith at inappropriate times, but you don’t have to hide it or apologize for it, either. It is part of who you are. If your clients don’t like it, they don’t have to hire you. Just don’t beat anyone over the head with it. (Ever. Even if it’s not a business situation.) I struggled with this for a while, because I wasn’t sure whether to let clients know I published a spiritual book—but I got nothing but respect from my clients when they found out.
  18. Know your limits. It’s one thing to stretch and grow. It’s another to get in way over your head. Don’t set yourself up to fail, and be humble enough to know when to admit failure or ask for help. (Those are two different things. Asking for help is not the same as failing.)
  19. Allow yourself to change. You can adapt and evolve your skills, your services, your way of doing business, the industries you work in, and how you charge people for your work. Just because you did it one way before doesn’t mean you have to do it that way forevermore.
  20. Believe in yourself. Not everyone else will support you the way you need them to, and not every client will be a good fit. Those things don’t mean you’re not qualified or competent. You have to have a sense of your inherent worth and hold onto that. I don’t mean you should be arrogant or boastful, just that you can’t let your sense of self-worth hinge on your clients’ responses to your work.
  21. Don’t take it personally. Not every client will like everything you do. The changes will seem arbitrary and frustrate the snot out of you. Some clients’ thought processes will baffle you. Chances are good, though, that they’re not rejecting you or saying you’re not a good designer—just that you haven’t yet given them what they had in mind.
  22. Learn to read between the lines. You’ll have to become proficient at understanding what a client is not saying, of figuring out what they can’t seem to articulate. This is one of the hardest things for me, because I don’t really do nuance—I am what you see, and I say what I mean. But recognize that people do not always communicate effectively, and part of your job is to learn to translate what they say into what they mean.
  23. This is business, not a social club. Sometimes, if you’re lucky, the client or other contractors may become your friends. Feel free to let them into your life and ask about theirs—but watch for clues, don’t push that on someone who clearly maintains a line between personal life and business, and know when you need to get back to work. I’ve been fortunate to work with people who have become good friends—which is great, because when you work a lot, it’s nice to enjoy the people you’re working with. But being friends isn’t a requirement for working well together.
  24. Do unto others… If you want respect, offer it. If you want consideration, be considerate. If you want honesty, don’t make up lies and excuses. People are perceptive and they know when you are not sincere, when they’re being taken advantage of or when they’re barely tolerated.
  25. Live life with a spirit of generosity. I’m not just talking about money. Cultivate an attitude of “what can I offer to them?” Or “how can I leave them better off than when I got here?” Go the extra mile. Do that little bit of extra. Don’t be afraid to share tips and tricks—just because someone else can do something doesn’t threaten your job security. You still have talent and experience others might not. Do not hold tightly to your work, your clients, your ideas, your business model, your skill set, your time. Offer it to God and then respond when He nudges you to offer it to someone else. There’s always more (of whatever it is) where that came from. And giving freely cultivates an attitude of kindness and generosity that overflows into all of your life.

CONTEST: Let me design a prayer prompt calendar just for you

I love to design my monthly prayer prompt calendars. I love the colors, the quirky connections, and coming up with the themes. There are more ideas than time to produce them. The hard part is narrowing it down and selecting a direction. That’s where you come in. Because you know what? I think there are lots of ...

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I love to design my monthly prayer prompt calendars. I love the colors, the quirky connections, and coming up with the themes. There are more ideas than time to produce them. The hard part is narrowing it down and selecting a direction. That’s where you come in.

Because you know what? I think there are lots of you out there with great ideas, too. And there are a lot of online ministries I’d be honored to help in this small way, so I decided to run a contest for bloggers.

Submit your idea for a theme for my March calendar before January 31, and if I select your idea, you win! You’ll get a calendar designed around that theme that you can give away on your blog (either free when they subscribe to your blog, or just as a free download for everyone—your choice how to promote it). I will also use it as the March calendar on my website, but I will publish it on my blog, linking to your blog, along with a brief introduction to you and your message.

You don’t have to be a designer to participate—in fact, I hope you’re not, because then I have more leeway! 🙂 Your idea does not have to be completely thought through, nor does it have to look like one of mine. The sample calendars throughout this post are provided to help you start thinking. Many of mine so far have centered on that month’s holidays, like Christmas or Valentine’s Day or summer, but even in those cases, I’ve gone in a certain thematic direction (love, thankfulness, etc.). Let yourself be creative! At the same time, know that I’ll choose one entry based on the possibilities I see to be creative with it, so you don’t really need to provide the creativity—and you never know what idea will intrigue me the most. Here are some examples of what I’m looking for. Your submission does not have to be any more detailed than the samples below.

Sample idea based on a graphic concept:

Chalkboard—calendar can look like a chalkboard with hand-drawn graphics and type, with the prompts themed around people who use chalk (teachers, kids, sidewalk artists, seamstresses, or what have you)

Sample idea based on a ministry topic:

A real example I created for a friend—she writes about being a single mom and the issues she faces, so I designed a calendar with prayers specific to her audience (your ministry may be about hope, or forgiveness, or renewal, or marriage, or love…)

Sample idea based on a scripture or Biblical theme:

Fruit of the spirit—prayer prompts might be about people who exhibit specific fruit and prayers for us to manifest those things (example: pray for someone who consistently shows joy; help me practice kindness) —OR—

Psalm 91 (“Whoever dwells in the shelter of the Most High will rest in the shadow of the Almighty. I will say of the Lord, “He is my refuge and my fortress, my God, in whom I trust.”)—calendar would include prayers about shelter (giving thanks for it), prompts related to things like protection, security, steadfastness, leaning on God, etc.

Sample idea based on book content (I’ll use my own because that’s an easy example):

Upside down—graphically, the type could be oriented in many different directions, and the prompts would be centered on unexpected people to pray for, ways to look at your own prayers differently or from a new perspective

or, say you write fiction:

Prayer prompts associated with your book, like people who share names with your characters; people who share professions or hobbies or quirks of a character; prompts about adventure or history or a specific place; and so on

Sample idea centered around specific people to pray for:

Prayers for children (infants and their parents; preschoolers; teens; athletes; someone struggling in school; kids whose parents recently divorced, etc.)

To enter, leave your ideas in a comment below or email me (kellyostanley@me.com). I need your website/blog URL and a brief description of your idea (doesn’t have to be any more detailed than the examples above) and how that relates to your site/ministry/message/book. You may include a sample prayer prompt or two, or not. If you have a certain style in mind, you can mention that (or show me a sample image)—or leave that part up to me.

If I select your entry, I will be in touch to learn more about your ministry and theme and to ask if you’d like to submit some of the specific prayer prompts as well. (Totally up to you; I am glad to come up with them myself, if you’d like.) Remember: deadline is January 31, and I’ll design the calendar by Feb. 20 so you have some time to promote it before March 1. Good luck! Can’t wait to hear your ideas!

P.S. I won’t use your ideas if you are not selected as the winner; they’ll remain yours, I promise. If you want to keep the ideas confidential, please submit to me by email with the subject line “prayer prompt contest.”

P.P.S. If you happen to be a man, I promise not to make the calendar look feminine or frilly. Don’t rule out this opportunity based on how my calendars have looked in the past. It just so happens that the majority of my readers are women, so I let myself be girly sometimes.


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