Lessons Learned in 25 Years of Freelancing

Embarking on a freelance web design career means embracing uncertainty. You’ll have to book enough gigs to keep you financially afloat. You’ll also need to weather the ups and downs. Most importantly, you’ll have to adjust to a changing landscape.

Nothing is guaranteed. Thus, I was astonished and amused when the calendar flipped to 2024. This year marks the 25th anniversary of my freelance business. How time flies.

I had no such milestones in mind back in 1999. My goals were relatively simple. I wanted to apply what I’d learned working for others. And I wanted to do things my way. Longevity wasn’t a priority for that 21-year-old kid.

Maybe I’ve beaten the odds. But I’m still working with clients. Some have even been with me for the entire run.

My goal today is to share some valuable lessons I’ve learned. Things that I hope will help you on your journey in this ever-changing industry. Here we go!

You Can Run Your Business Your Way

The world is full of copycats. Freelance web designers are no exception. We look at our peers and want to keep up with them. It’s a competitive field, after all.

Still, blending in makes it hard to stand out. Thus, trying to be like everyone else won’t get you far.

Think about what you want to accomplish. Ask yourself:

  • What kinds of projects do I prefer?
  • What technologies will I use?
  • What’s my ideal work environment?
  • What will my work schedule look like?

You can build the business you want. Now, you may need to make some sacrifices along the way. Not everything will go according to plan. However, you have an opportunity to work towards the future you envision.

The same principle applies to marketing. Your website doesn’t have to look anyone else’s. Nor do you have to hide your personality.

Show the world the best version of yourself. And don’t be afraid to do things your way. You’ll position yourself for happiness in the long term.

Lessons Learned in 25 Years of Freelancing

You’ll Change When the Time Is Right

The web design industry has come a long way in 25 years. We went from hand-coding HTML to content management systems (CMS) like WordPress. We went from employing layout hacks to using native CSS specifications. And that’s just the tip of the iceberg.

There’s a constant pressure to change and adapt. A steady flow of new tools and techniques arrives almost daily. It’s easy to feel left behind.

However, I’ve found that changes occur organically. There’s a time when making a change makes sense. You may outgrow your current workflow. Or you might book a project that would benefit from a different approach.

WordPress is a prime example. I didn’t shift my business to WordPress the moment it became popular. I came to it out of need.

Clients began asking for more complex websites. WordPress allowed me to build them more efficiently. Eventually, I decided to focus on it exclusively.

You don’t have to force yourself into changing. Instead, take action when it feels right.

There's no rush to change the tools and technologies you use.

Make Time for Personal and Professional Growth

Busy freelancers can become overwhelmed with projects. Spending all of your time working could lead to burnout. Not to mention fewer opportunities to learn.

It’s easy to fall into this trap. Making money and crossing items off your to-do list are priorities. But at what cost?

We rely heavily on our brains. Crafting designs and writing code requires mental fitness. A tired mind is less creative and less productive.

You need space to breathe. But no one will tell you to slow down. The responsibility is yours alone.

Schedule some time out of the office. That could be anything from a vacation to a daily walk. It’s a chance for a mental and physical reset.

Also, consider the importance of education. Learning a new skill or improving an existing one makes you better. It raises confidence and increases your earning potential.

The idea is to be mindful of your time. Use it wisely and allow yourself to rest and grow.

Be deliberate in giving yourself time away.

Be Careful Who You Work With

There is a temptation to book every gig that comes your way. On the surface, it makes sense. You build websites. The client needs a website. Everybody’s happy.

Freelancing is a long-term commitment, however. The project you accept today could be with you for years. Sometimes that’s a positive. But it can also be a drag on your business.

The issue can take a couple of forms. One is the classic “difficult” client. They’re picky and argue about every dollar. You dread your encounters with them. Do you want to be stuck in this situation for a decade or more?

On the other side, not all projects will fit your business. Maybe it uses a tool you no longer work with. Or the revenue doesn’t match the required effort.

It’s OK to be choosy when it comes to clients. So, keep the future in mind when considering a project. A little foresight can save you a lot of headaches.

Choose projects and clients that fit your business goals.

Customer Service Makes All the Difference

There is no shortage of web designers out there. Everyone from freelancers to agencies is looking to boost their bottom line. And there are only so many projects to go around.

There’s a myth that you must be the best designer or coder to succeed. Sure, skill and talent mean a lot. However, clients may not be able to discern your skills from others. To them, you might be one of many options.

Therefore, the customer experience is another way to stand out. Give your clients more than they expect. It will keep them happy and encourage them to refer others to you.

Providing top-notch customer service is easier than you think. For example, these simple practices can make a positive impact:

  • Answer client inquiries promptly and politely;
  • Be honest with your project assessments;
  • Explain technical concepts in plain language;
  • Listen to your clients and help them determine their needs;
  • Keep an open line of communication;
  • Deliver on your promises;

Customer service can pay dividends for years to come. And it’s as important as any technical skill.

Some of your competitors don’t measure up in this area. Take advantage and give yourself an edge.

Providing great customer service will separate you from competitors.

The Freelance Experience Is What You Make It

Being a freelancer takes a lot of effort. You must be willing to earn your way to success. And you’ll have to start building from the ground up.

However, you’ll also have a chance to define your vision for success. From there, you can craft a plan to achieve your goals. It could take years.

Thus, the lifestyle may not be a fit for everyone. But it’s possible for those who want to make that commitment. I’m living proof.

What will freelancing look like in another 25 years? Will I still be working then? Time will tell. My experiences so far have given me hope.

Good luck – wherever you are in your freelance journey. Keep going and make the most out of the opportunity. Take time to celebrate your milestones – you’ve earned it!

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Professor Edward Roberts, management scholar, champion of entrepreneurship, and “MIT icon,” dies at 88

Professor Edward Roberts, management scholar, champion of entrepreneurship, and “MIT icon,” dies at 88

Edward B. Roberts ’58, SM ’58, SM ’60, PhD ’62, a visionary management professor who studied entrepreneurship while building a flourishing innovation ecosystem at MIT, died on Tuesday. He was 88 years old.

Over a remarkable seven-decade career at the Institute, Roberts was a prolific scholar and mentor who founded what is now the Martin Trust Center for MIT Entrepreneurship, a unique resource that has guided thousands of innovators as they have brought inventions and ideas to the market.

Roberts, the David Sarnoff Professor of Management of Technology at the MIT Sloan School of Management, was an energetic and encouraging presence who espoused the value of founding companies organized around a clear core idea, and of having significant new technology to apply to that idea. Generations of MIT students as well as faculty found a path forward for their startups as a result, benefitting from the structure of the Martin Trust Center and influenced by Roberts’ work.

“It is not too much to say that MIT’s flourishing entrepreneurial culture and global reputation as a source of influential start-ups grew from seeds Ed planted here 50 years ago,” MIT President Sally Kornbluth wrote in a letter to the MIT community yesterday.

Kornbluth called Roberts an “MIT icon” who was “always doing things no one had done before,” including “pioneering the very idea that entrepreneurship is a craft that can be systematically studied and successfully taught.”

In 2015 Roberts co-authored a report estimating that, as of 2014, MIT alumni had launched 30,200 active companies employing roughly 4.6 million people and generating roughly $1.9 trillion in annual revenues, a figure that would have ranked among the top 10 countries in the world in GDP.

“I have helped MIT to become a much more entrepreneurial place,” Roberts said — in something of an understatement — during a 2011 interview for an MIT Sloan oral history series.

Wide-ranging intellect, entrepreneurial spirit

Born in 1935, Roberts grew up in nearby Chelsea, Massachusetts, commuting to MIT as an undergraduate. Through his intellectual life as a student, as well as his later career as a scholar, Roberts personified the interdisciplinary possibilities of MIT.

Even while earning his undergraduate degree and a master’s degree in electrical engineering, Roberts was often taking two additional courses in economics and at MIT Sloan — despite, as he once recalled, the vocal concerns of his faculty advisor.

As a graduate student, by the late 1950s, Roberts had begun working with MIT faculty member Jay Forrester, a computing pioneer who had started developing many core ideas now integral to the study of system dynamics. Roberts became increasingly interested in the application of those ideas to management, also helping to create a framework for the field then known as industrial dynamics.

Assisted by the extra courses he had already been taking, Roberts earned his master’s in management from MIT Sloan, and then his PhD in economics, with his doctoral work focused on applying system dynamics to the management of research and development. It was MIT’s first doctoral dissertation in system dynamics.

Having joined MIT as a student, Roberts never left. He took a position as a faculty member at MIT Sloan and began working on wide-ranging and important studies of organizational practices in areas that included health care management, among other things.

Along the way, Roberts practiced what he advocated: In the 1960s, while still a junior faculty member, he co-founded his own firm, Pugh-Roberts Associates, which took the ideas of system dynamics to partners in the private sector and government. The firm still exists today, as the Sage Analysis Group.

The books Roberts co-authored early in his career include “The Persistent Poppy” (1975), examining the social and economic impact of heroin use, and “The Dynamics of Human Service Delivery” (1976), applying system dynamics analysis to the service sector.

Over time, Roberts’ work became increasingly focused on the components of successful entrepreneurship. His high-profile 1991 book, Entrepreneurs in High-Technology: Lessons from MIT and Beyond,” was based on a thorough examination of 113 companies founded by entrepreneurs, moving the field forward through its extensive empirical work.

That overlapped with Roberts’ work building a framework for encouraging entrepreneurship at MIT. The MIT Center for Entrepreneurship opened in 1990, providing an essential resource for potential firm founders at the Institute. As the center grew, Roberts himself became a vital figure to many budding entrepreneurs, a vigorous presence offering input based on expert analysis.

“Ed will always be remembered at MIT Sloan as a campus pillar,” wrote Georgia Perakis, interim John C. Head III Dean of MIT Sloan, along with Deputy Dean Michael Cusumano, in a letter to the MIT Sloan community on Tuesday. “He could be found walking the halls, visiting faculty, staff, students, and alumni at the school, and sharing with them parts of the history of MIT Sloan. He remained connected to generations of MIT entrepreneurs, offering advice and guidance as companies were launched. Those of us who knew Ed count ourselves lucky to have had his counsel and will miss him dearly.”

“Virtually everything today in the MIT entrepreneurial ecosystem, from classes to extracurricular activities, has some level of Ed’s DNA at it core,” says Bill Aulet, professor of the practice at MIT Sloan and the managing director of the Martin Trust Center for MIT Entrepreneurship. “But his impact also went well beyond MIT, where Ed Roberts was a generational figure in entrepreneurship as a field of research and instruction.”

MIT faculty who studied with Roberts also recall the impact his teaching had on their own careers.

“I, and many others in the system dynamics group here, took Ed’s course as a doctoral student and learned a great deal about how to work with policymakers and other leaders to increase the chances that the results of modeling would be implemented and have sustained beneficial impact in organizations,” recalls John Sterman, the Jay W. Forrester Professor of Management at MIT Sloan and a professor in the Institute for Data, Systems, and Society.

A celebration of MIT pioneers

In all, Roberts published 12 books and over 160 articles on entrepreneurship and management, with an audience both inside academia and in technology-driven growth industries.

Among his recent works, Roberts’ 2020 book, Celebrating Entrepreneurs: How MIT Nurtured Pioneering Entrepreneurs Who Built Great Companies,” examined how the Institute developed its formal framework and culture of entrepreneurship across a variety of industries.

In addition to founding the Martin Trust Center for MIT Entrepreneurship, Roberts at one point chaired the MIT Management of Technology (MOT) program. He also co-created the MIT Sloan Entrepreneurship and Innovation Certificate program.

Roberts was also an active presence as a co-founder, board member, and investor in startups, including the health care information firm Medical Information Technology, Inc. In addition, Roberts co-founded a group of Zero Stage Capital equity funds, which provided early-stage capital for promising tech startups. All told, Roberts was a board member for more than 40 firms and a co-founder of 14 companies.

Roberts is survived by his wife, Nancy; his children, Valerie and her husband, Mark Friedman, Mitchell and his wife, Jill, and Andrea and her husband, Marc Foster; and nine grandchildren. Donations can be made to the Combined Jewish Philanthropies of Boston in his memory.

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