Why I Took on a Low-Paying Project

The client for this project is an old friend. They’re starting a new business, full of passion and drive, but lacking the experience to articulate their brand clearly. They have big ideas but don’t have the budget to bring in high-level marketing help. I’ve been working on a new service offering tailored for business owners like them—something designed to help startups and solopreneurs get the right foundation in place.

This project allows me to refine and implement my new offering. Instead of waiting for the ideal client to come along, I chose to test it out in a real-world scenario. The fee is lower than my usual rate, but the opportunity cost makes sense. I gain valuable insights, improve my process, and provide my friend with the support they need to move forward. In the long run, this experience will make my service more effective and marketable to future clients.

Opportunity vs. Profit: A Strategic Mindset Shift

In business, we’re often conditioned to think in immediate returns: How much money will this project bring in right now? But if we take a step back and assess the bigger picture, we realize that some opportunities provide returns in different ways:

1. Skill Development & Experimentation – Offering a new service, testing a new pricing model, or experimenting with a different workflow can be worth far more than a quick financial gain.
2. Relationship Building – People remember who helped them in the early stages. A small favor today can lead to a high-value client tomorrow.
3. Market Research & Proof of Concept – Working with an actual client in a new capacity helps refine your approach before scaling it.
4. Credibility & Referrals – A satisfied client, even at a lower rate, can become a strong advocate for your services and bring in future business.
5. Personal Fulfillment – Sometimes, the satisfaction of making an impact outweighs the financial return.

Finding the Right Opportunities to Take On

Of course, not every low-paying project is worth your time. Here are some guidelines for identifying when an opportunity is strategically valuable:

• Does it align with your long-term goals? If the project helps you refine a service you want to offer at scale, it’s a smart move.
• Does it provide learning opportunities? If you’ll gain new skills, insights, or case studies from the experience, it’s worth considering.
• Does it strengthen a key relationship? Helping someone who might later become a valuable client or referral source is an investment.
• Does it have the potential to open doors? A project that puts you in front of a new audience or builds credibility in a new niche can be highly valuable.

When to Say No

Not every small project is an opportunity. If it distracts from your main business goals, takes too much time, or involves demanding clients with no future potential, it’s okay to say no. The key is to differentiate between a low-value project and one that offers strategic benefits beyond immediate revenue.

The Bigger Picture

Taking on a project for the long-term opportunity rather than immediate profit isn’t about working for free or undervaluing yourself. It’s about being strategic with your choices and recognizing when an investment in time and experience will pay off down the road.

Some of the best opportunities don’t show up in the form of a high-dollar contract. They come disguised as small projects, collaborations, or experiments that allow you to refine your skills, build relationships, and create something bigger than the project itself.

Would some business coaches tell me this was a mistake? Maybe. But I believe that when you focus on creating value, the money always follows.

Sound familiar? If you work for yourself and generally by yourself, you’ve probably found yourself stuck in decision-making mode more times than you’d like to admit.

When running a one-person business, every decision feels high-stakes—because you are the business. You don’t have a team to bounce ideas off and no boss to give you directives. Every choice, from pricing your services to picking a marketing strategy, falls squarely on your shoulders.

And when there are too many options, it’s easy to wait. Wait for the “perfect” choice. Wait for more information. Wait for a sign.

Why We Get Stuck

Overthinking decisions often comes down to three things:

1. Fear of making the wrong choice. You worry that you’ll waste time, lose money, or hurt your reputation if you choose wrong.
2. Fear of missing out on a better option. FOBO makes you hesitate, thinking something better might come along if you wait just a little longer.
3. Perfectionism. You want to get it just right, so you delay action in the name of more research, more planning, more thinking.

But here’s the truth: Not deciding is a decision in itself. And often, it’s the worst one you can make.

You Probably Already Know What to Do

Deep down, you likely already know the next step to take. But instead of taking action, you hesitate—overanalyzing, second-guessing, and getting lost in a loop of “what-ifs.”

• What if I pick the wrong niche?
• What if I price my services too high—or too low?
• What if I launch my website and nobody cares?

Here’s the thing: There is no perfect decision. Only the best decision you can make right now with the information you have.

And the only way to know if something will work? Take action.

Progress Beats Perfection Every Time

Running a business isn’t about getting it right every time—it’s about experimenting, learning, and adapting.

Instead of agonizing over the perfect decision, try this instead:

1. Make a choice. Pick the best option based on what you know right now.
2. Take action. Implement the decision and give it time to play out.
3. Evaluate. Did it work? What did you learn?
4. Adjust as needed. If it didn’t work as expected, tweak it or try something else.

This mindset shift—from seeking perfection to focusing on progress—is the key to moving forward.

Treat Decisions as Iterations, Not Final Answers

Most decisions in business aren’t permanent. They’re tests.

• Your pricing isn’t set in stone—you can adjust it as you learn more about your market.
• Your website isn’t forever—you can tweak the messaging or design anytime.
• Your marketing strategy isn’t one-and-done—it’s an ongoing experiment.

The faster you make decisions, the quicker you get real-world feedback. And that feedback is what helps you refine, improve, and grow.

Closing the Loop On this…

Every successful business owner you admire has made plenty of mistakes along the way. The difference? They didn’t let overthinking stop them from starting.

So, what decision have you been putting off? Take the next step today—because action is what creates clarity, not the other way around.

The Benefits of Downtime

It’s easy to overlook the fundamental need for rest and rejuvenation. However, stepping away from the daily grind isn’t just beneficial—it’s essential for your overall well-being and the health of your business. Regular breaks offer a unique opportunity to disconnect from immediate pressures, providing the mental space needed to gain fresh insights and perspectives. This time away instils a sense of balance, allowing you to return to your work with a clearer mind and a more focused, strategic approach. Prioritizing downtime helps you reconnect with your passion and purpose, ensuring that your entrepreneurial journey remains sustainable and fulfilling. Here’s why every solopreneur and business owner should prioritize taking time off:

Preventing Burnout: Ever felt like you’re running on empty? That’s burnout creeping in. Downtime lets you step away, recharge, and return with renewed energy and focus. Whether a short vacation or a day pursuing personal interests, these breaks are crucial for your mental and emotional well-being.

Cultivating Creativity: Creativity thrives when the mind is relaxed. Taking a break from your business lets you gain fresh perspectives and generate innovative ideas. Whether trying new hobbies, exploring new places, or simply relaxing, downtime sparks creativity by exposing you to new experiences and inspirations.

Improving Decision Making: Constant work without breaks can lead to decision fatigue, affecting the quality of your choices. Taking time off helps you approach challenges with clarity and make better decisions aligned with your business goals.

Enhancing Productivity: Ironically, downtime can boost productivity at work. Stepping back periodically prevents overwork, allows you to return to work with increased efficiency, and allows you to focus on what matters most for your business.

Maintaining Work-Life Balance: Solopreneurs and small business owners often blur the lines between work and personal life. Downtime helps you set boundaries, prioritize self-care, and nurture personal relationships. Achieving a balanced life sustains your entrepreneurial journey in the long run.

Downtime Options: Vacation vs. Sabbatical

Vacation: Refresh and Reconnect

Whether a short getaway or an extended trip, taking a vacation is a classic way to recharge as a solopreneur. It’s a chance to unwind, explore new places, and immerse yourself in different experiences. Whether you choose a relaxing beach retreat, an adventurous hiking trip, or exploring a new city, vacations provide a crucial break from your daily business routine.

Benefits of Vacation:

• Physical and Mental Renewal: Stepping away allows your mind and body to recover from stress, ensuring you return with renewed vigor.
• New Perspectives: Traveling exposes you to different cultures and environments, sparking creativity and inspiring new ideas for your business.
• Quality Time: Vacations offer an opportunity to strengthen personal relationships and reconnect with loved ones.

Sabbatical: Deep Dive into Personal Or Professional Growth

A sabbatical is a break aimed at personal and professional development. It’s a chance to pursue passion projects, learn new skills, or simply reflect without the day-to-day pressures of your business.

Benefits of Sabbatical:

• Focused Self-Improvement: Use this time to enhance your skills, explore new interests, or strategize for your business’s future.
• Strategic Planning: Step back to assess your business from a broader perspective, refine strategies, and set ambitious goals.
• Renewed Inspiration: Engaging in activities outside your routine reignites your passion and creativity, bringing fresh energy to your entrepreneurial endeavors.

Choosing the Right Downtime Strategy

Deciding between a vacation and a sabbatical depends on your current needs and goals. Vacations are ideal for rejuvenation, while sabbaticals offer a deeper exploration of personal growth and business strategy. Both options are invaluable investments in your well-being and the long-term success of your business. Remember, downtime isn’t just about resting—it’s about recharging your creativity, enhancing productivity, and ensuring sustainable success as a business owner over the long haul.

There are many reasons why New Year’s resolutions may not work. Some common causes include setting unrealistic goals, not having a clear plan or strategy for achieving the goal, losing motivation or interest over time, and not tracking progress or accountability. Additionally, some people may be more successful at achieving their resolutions than others due to their level of commitment, ability to handle setbacks or obstacles, and overall support system.

Monthly, or Mico-resolutions to the rescue.

This is why the monthly resolution works so well. Whether you call it a resolution, micro-resolution, or micro-goal, the results will be the same; instead of your attention being pulled in multiple directions, you’re forcing yourself to focus on just one thing. 

You could set for yourself 12 habits you want to build or change throughout the year but focus on just one each month. After all, they say that if you do something new consistently for 30 consecutive days, it will become so routine that you don’t even think about it anymore. 

Or your monthly resolutions could be different each month, like focusing on a habit one month, completing a personal project the next, or whatever great big substantiative goal you want to achieve within 30 days.

One month last year, my resolution was to “protect my time,” which meant saying no to projects and meetings that didn’t advance my more significant over-arching business and personal goals.

The benefits of monthly resolutions

One of the benefits of monthly resolutions is that they help you stay motivated and engaged. When you create a long list of New Years’ resolutions, it’s easy to lose sight of your progress and become discouraged. With monthly resolutions, you can see your progress more frequently, which can help you stay motivated and on track. 

Another benefit to monthly resolutions is that you stay motivated. Monthly resolutions help you build momentum and increase your chances of success. Achieving a small goal can give you a sense of accomplishment and encourage you to keep going. 

Since starting my monthly resolutions, I have accomplished much more throughout the year, and favorable resolutions were more easily achievable than negative ones. Meaning that resolutions to create, revise, or improve something felt better to work on a little bit each day than resolutions that started with the words “don’t” or “stop.”

There are two crucial things to remember about this process. First, you need to write your monthly resolution down so you can see it in front of you daily. Put it in your calendar, write it on a post-it, write it down in your daily journal, whatever it takes. Second, be flexible and keep going even if progress is made slower than you like. Some resolutions take more time and effort. I’ve even carried a resolution over into the next month from time to time.

Do you want to make 2023 your most productive year ever? Are you wondering, “how am I going to get everything on my to-do list done?” I can help; just reach out for a chat.

A “start, stop, continue” list is a helpful tool for reflection and growth. For a business, it can be used to identify projects, initiatives, and activities that are worth starting, stopping, or continuing to achieve specific business goals.

Doing a “start, stop, continue” list can be a valuable exercise for helping you identify areas of your business where you can make positive changes. It is a simple but effective way to reflect on your current business activities and plan to move forward in a more positive direction.

To do a “start, stop, continue” list, you actually need to make three separate lists: one for things you want to start doing, one for things you want to stop doing, and one for something you want to continue doing. This exercise can be done for any business area, such as operations, marketing, and finance.

For the “start” list, think about things you want to start doing to improve your business or reach your goals. This could include reaching out to past clients, attending trade shows, or writing a monthly blog. The key is to make these things specific and achievable, so you can focus on making progress toward them.

For the “stop” list, think about things you want to stop doing that may be holding you back or causing problems for your business. This could include things like procrastinating, overspending, or engaging in unproductive tasks. By identifying these habits and behaviors, you can start working on making positive changes.

For the “continue” list, think about things you are already doing that are working well for your business and that you want to keep doing. This could include things like staying organized, attending strategic networking events, or collecting customer reviews. You can build on your current strengths and successes by continuing to do these things.

Once you have made your “start, stop, continue” lists, you can use them as a roadmap for making positive changes in your business. You can set goals for each item on your “start” and “stop” lists and develop a plan for achieving those goals. One way to do this is to use the SMART goal-setting framework, which stands for Specific, Measurable, Achievable, Relevant, and Time-bound. By setting SMART goals, you can increase your chances of success and make progress toward your objectives.

In addition to setting goals, you can do a few other things to increase your chances of success when working on your “start, stop, continue” list. First, enlisting the support of employees, contractors, family, or a coach or mentor can be helpful. Having someone to hold you accountable and cheer you on can make a big difference in your ability to achieve your goals.

Second, it is essential to be flexible and not get discouraged if progress is not made as quickly as desired, as long-term behavior change can take time and effort. Finally, it can be helpful to track your progress along the way, using tools like a journal, spreadsheet, or app to help you stay on track.

Overall, doing a “start, stop, continue” list is a simple but powerful way to reflect on your current activities, habits, and behaviors and plan how to move forward in a more positive direction. By identifying the things you want to start, stop, and continue doing and setting specific and achievable goals, you can work towards making positive changes in your life. By enlisting the support of others, being flexible, and tracking your progress, you can increase your chances of success and make meaningful progress toward your objectives

By the end of 2015, after spending nearly eight years as an in-house creative director—and over 20 years in the field—I found myself self-employed for the second time in my career. As I enter my fourth year as a brand and creative strategy consultant, I can attribute much of my success as a business owner to the lessons I learned while working in-house.

Reflecting on my time leading in-house creative teams, I realize that my consulting mindset and teaching instincts significantly impacted my success. Whether you’re leading an in-house team or running your own business, certain principles remain the same and are critical to your success.

Remember, You Are Running a Business

Being a creative leader isn’t just about overseeing the work of designers, writers, photographers, and videographers—it’s also about understanding how to run a business. As an in-house leader, you manage a corporation’s business unit. That means implementing processes, procedures, and policies to ensure smooth operations. Some organizations even document these structures to maintain continuity.

Your role as a leader is to continually reassess, reevaluate, and refine how your team operates to maximize efficiency.

This operational mindset is just as essential when you’re self-employed. Running your own business requires strategic planning, adaptability, and a solid operational foundation. By documenting every aspect of your business—from marketing to client work to billing—you’ll gain clarity on your processes and identify areas for improvement, making your business more efficient and profitable.

Relationships Are Everything

I’ve believed in the power of networking since I was a teenager. It helped me land my first freelance job, full-time position after college, and corporate role at Banana Republic. When I transitioned to Gap, it was because of networking. My previous freelance business (1999–2007) and my current consulting firm thrive because of strong professional connections.

However, many people approach networking the wrong way. It’s not about casting a wide net—it’s about connecting with the right people. Two principles I’ve found to be consistently true in business:

• It’s not what you know, but who you know.
• Building strong relationships is more important than having a big network.

For self-employed creatives, networking helps build awareness, generate referrals, and create strategic partnerships. But for in-house leaders, it’s just as critical. You can’t operate in a corporate bubble. You must build relationships with internal clients, peers, and key decision-makers. These connections make it easier to sell creative ideas, advocate for your team, and secure the resources you need. A well-cultivated network within your organization will serve as an extension of your department, advocating for you and your team.

Manage Your Time Like the Rare Commodity It Is

If there’s one skill every creative leader—whether in-house or self-employed—needs to master, it’s this: Learn to say “no.”

You need to say “no” to unnecessary meetings, distractions, and anything that doesn’t add value to your work. There are two key reasons for this:

1. You have too much work to waste time in unnecessary meetings.
2. Being too available sends the wrong message.

Creative leaders are often pulled into too many meetings—project discussions, corporate updates, and impromptu brainstorming sessions. While some are necessary, many are not. A “meeting culture” can be detrimental to productivity and morale. I’ve even attended meetings that existed solely to plan more meetings!

Frequent interruptions, whether meetings or impromptu drop-ins, disrupt creative flow and drain valuable time. The result? You end up working late or over the weekend to catch up.

How to Take Control of Your Time:

• Be selective about meetings. Before attending, ask yourself: Do I really need to be there? If not, delegate it to a direct report and have them update you later.
• Emphasize efficiency. Many meetings could be replaced with a quick phone call or email.
• Set boundaries. Protect your deep work time by limiting distractions and unnecessary interruptions.

For consultants, time management is even more crucial. Beyond client work, you must also handle business development, marketing, finance, and more. Networking is essential, but it must be strategic. Before committing, ask: Will this meeting or event lead to a referral, partnership, or new client? If the answer isn’t a resounding yes, it’s a hard no.

Transitioning from in-house leadership to running my own business has reinforced these key principles. Whether leading a team within a corporation or managing my consultancy, success depends on strategic operations, strong relationships, and smart time management. By remembering these lessons, you can navigate both worlds confidently and efficiently.

So I had to discover for myself the career potential of, and how to go about landing, a job in graphic design. Early on I was introduced to the trade publications of our profession such as Communication Arts, Graphis, Dynamic Graphics, GDUSA, PRINT and HOW. I joined AIGA and the Art Directors Club as a student and started going to events and networking during my first year of college because that’s just what we did in the pre-internet era.

I started working professionally as a freelancer before I graduated from the School of Visual Arts; I later gained experience working in-house. My career so far has included being a front-line designer, creative director, and in-house creative services leader in a variety of industries, and I have also been self-employed (twice) serving my own clients.

Since 2001, I have been teaching design, marketing and branding to undergraduate and graduate students and have served on the board of directors of InSource—a professional association of in-house creative leaders—since 2007, leading the organization as President since 2010. So you could say I have had a diverse career practicing and serving within the design field.

In my roles as an educator, corporate in-house leader, and leader of InSource, I am most often asked by designers who are just starting out on their own career journey: “Which is better, an in-house or agency job?” My answer is always the same: “It depends. It depends on what kind of work you want to do, what stage of your career you are in, what stage of your life you are in and what you want to do with your career.”

When faced with the “thanks for not answering my question” eye roll, I then—as most teachers do—begin to make my point by telling my own abbreviated story about my career journey.

These two short articles are my written version of what I tell my students and young designers to help them better understand some of the differences between working at an agency or in-house as a freelancer or an employee, leading a creative team or working for yourself.

Some advice I once received on choosing among career paths

I’m going to start this off with some sage advice I received about 10 years ago when I was somewhere at the midpoint of my career. This advice came from a colleague of mine at KPMG—one of the “big four” audit, tax and advisory services firms—when I was leading the creative team that I had started there. She worked in a different department but had become a mentor to me while working at the firm. She told me about a time when her own mentor relayed the following advice: “There are three reasons people choose to work for a living: stability, money or advancement.”

“Some people get a job and work because they just want to have a consistent income and a place to do what they do,” she said. “Those people just want stability in their lives, and want a regular paycheck and benefits. They are not seeking recognition or advancement.”

“Some people will work harder not for recognition, but because they want more money,” she continued. “They do whatever they have to do to make a bigger paycheck. Perhaps that’s working overtime or going above and beyond what is asked of them for a bigger bonus. Whatever they’re doing, it is driven by money.”

“And some people are ladder climbers,” she said. “These people work for recognition and the advancement to leadership positions that comes with that recognition. While advancement does often come with more money, that’s not the driver. No, the driver is the power that comes from leadership.”

“Andy,” she said, “you need to figure out why you work every day.”

I sat back in the chair and thought about what she had just told me. I had come to her on a particularly difficult day at work, wondering if I had a future in the firm…or even in this business. And after a few minutes, I said, “I think there’s a fourth reason people work that especially applies to anyone in the creative field.”

“Oh really? What’s that?” she asked.

“Passion,” I replied. “I think designers, and creative people in general, also work because they are passionate about what they do. They love it, they believe in it and they know what they’re doing can help a business be successful.”

Stability, money, advancement or passion. Those are, in my opinion, the four reasons why people work. Whatever reason you may have for choosing freelance versus agency versus in-house work totally depends on what’s driving you to work each day.

Freelance, “perma-lance,” and the first salaried job in design.

it’s hard to believe I’ve been at this for 25 years. Few people in my network of friends and colleagues have stuck with the same career for so long. Many of my peers who I graduated with from SVA gave up on design a long time ago for something else completely. As I started to wonder why they left this career (because it certainly wasn’t a lack of talent) I started to reflect on what the field looked like back when I started.

When I was just starting out, the thought of a designer going in-house was almost unheard of. We were educated to believe that the best work was being done by ad agencies and design studios, and your best bet starting out was to get a freelance gig starting at the bottom and proving yourself to move up to the juicy client work. Then eventually, you go out and build your own book of business until you had a full-blown agency/studio of your own. So that’s what I did…at first.

The freelance lifestyle

I hustled as much as I could to get my own (small) freelance clients, while also freelancing for a couple of small studios in New York City. The pay was low ($12 – $15 per hour), and little of the work was going to make it into my portfolio since it was the-low-man-on-the-totem-pole production design. But that was OK for me at the time because the hours were good, and the studio owners were teaching me a lot about the business.

I was an onsite freelance designer at three different companies at the same time. I had three different rates, kept a timesheet and project log, and submitted a weekly invoice directly to my boss(es) to be paid. There were no client meetings. No division meetings. No company all-hands meetings. No responsibilities other than the project load on my plate. I felt like I was living the young professional’s dream at 26 years old. I went out and bought myself a beeper! (Google it if you’re too young to remember those.)

But after about a year I got restless creatively and also wanted to make more money. I was ready for better work. Work that I would be really proud of that stretched my creative muscles. I received a call from a friend about a part-time freelance opening at fashion retailer Banana Republic, designing tee shirts and apparel graphics. It paid twice what I was making per hour at that time, I would be working in a department with other designers, and there was a good chance my designs would end up in stores.

The perma-lance job

The part-time freelance gig at Banana Republic eventually became a full-time freelance gig, escalating to 60 hours per week periodically as we approached crunch time for getting designs into the buyer’s hands. I started being invited to creative brainstorming meetings, then got sent out to handle internal clients on my own.

This was great! I was doing creative work, being paid really well, and I started to feel like I was part of the company. Like I belonged there. I didn’t really feel like a freelancer anymore. But I wasn’t an employee either. I was something else. I was a perma-lancer (“permanent freelancer”). This was in the days before laws were in place regarding what constitutes an “employee” by the way. But once those laws kicked in we were told that we would need to reduce the number of hours we worked and would need to leave altogether after a certain period of time to avoid classification as an employee (something the company didn’t want, and why they had us in the first place).

After 3.5 years of doing fun work, making friends, and making great money (for a designer at that time) I knew the end was coming. Which it eventually did, but not because of the employment laws. Banana had decided they were no longer going to be doing graphic tees and apparel. On that Friday, we were told not to come in on Monday.

Besides the potential for the gig to come to an end at any time, making it an unstable job, another downside to working as a freelancer is the lack of affordable benefits. As a freelancer, your hourly rate should account for the cost of living expenses, including insurance. And when you’re being paid a straight check without payroll deductions (taxes) being handled for you, you’re going to need to save at least 30% of everything you make to pay income taxes yourself. In other words, you’re living the 1099 life.

Full-time employee

But that all changed for me exactly one week later. Being the hustler that I am, I reached out to the Art Director of Gap brand’s creative department saying I was available. I had two days of interviews on the Monday and Tuesday I would normally have been at my desk at Banana Republic, and was offered a full-time job with GapKids, with a great salary (more than freelance paid) and benefits. This was the first time I ever got paid to take a vacation. Whoa!

But then I realized something… I was in-house now. In fact, I had been since starting at Banana Republic, or at least I considered myself to be in-house—that is I felt like I was part of the company. I felt like I was doing work that was strategically aligned with the business, and I felt like I had a vested interest in the health of the company.

With freelance, you don’t often feel like you have a vested interest in how well a company does. It’s a gig, just like any other gig. There will be other clients to do work for. You’re a hired gun, and you’ll be lucky/happy if they hire you again for another gig.

But feeling invested in something is different. You budget for projects differently (and if you own shares of the company, you treat department money like it’s your own). You approach creative challenges differently (more strategically). You become embedded in the brand and begin to have a history with it.
Was that such a bad thing after all?

Now to be fair, I’ve never been a full-time employee at an agency or design studio. I’ve heard that it’s no more stable then onsite freelancing. So I’d like to hear your thoughts on the differences in the comments below.