25 Lessons in Business (After 25 Years)

Editor’s note: This is a guest post by Lisa Robbin Young.

’Tis the season for annual reviews and reflections on the last decade. The beginning of the year for me, however, always has a tinge more gravitas because it’s also close to my own birthday. I turned 45 yesterday and I’ve been an online entrepreneur for over 25 years now. So, 2020 is a convergence of milestones for me. As I prepped for my own year/decade in review, I penned 25 lessons from 25 years in business to share with you.

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1. Strategies shift. Relationships are what matter most.

Back in 1994, when the Internet was barely old enough to drink, and the World Wide Web was still in diapers, I built one of the first-ever e-commerce websites. So much has changed in the online landscape since the days of building websites “by hand” using Windows Notepad or HotDog.

And yet, while the dotcom bubble has both risen and burst in that time, there’s a lot about building a business, online or off, that hasn’t changed. People are still the core driver of business. Relationships still matter. Hope, by itself, is still not a strategy.

As your market matures, your strategy will need to mature, shift, and grow along with it. The best and most timeless strategy of all is paying attention to your audience. Get to know them. Be aware of what they’re doing, where they’ve been, and where they’re going. The tools and tactics you use to make that happen will vary over time.

2. It’s not about the platform.

Back in the 1990s, AOL, Angelfire, and Geocities were the popular platforms. Then, ICQ and SixDegrees, followed by Messenger, Napster, Myspace, and Skype. All before the “upstart” we now know as Facebook. Reddit, Twitter, and Instagram didn’t join the party until about 10 years ago.

Like any market reaching saturation, we’re seeing a lot of buying and selling of platforms as media companies seek to dominate the market. It doesn’t matter what market you’re in, it always starts with a trickle, then expansion, followed by a contraction of the market.

Platforms come and go. Some of them will be great for you for a while, and others won’t work for the way you work. That’s normal. You can’t be everywhere all the time effectively. Stick to what works for you and be aware that things can change. Don’t get tied to one platform — unless it’s one you own.

3. Success is personal. The best success comes when you are in alignment with your values.

One of the things I tell my A-Club clients is that the best way to be successful is to define success on your own terms. When you are clear on what success looks like for you, it’s easier to stay committed to doing the work necessary to achieve it.

Stay true to what really matters to you. I mean that personally as well as professionally. You may not need to build a six- or seven-figure business to achieve your personal definition of success. That’s fantastic! Don’t let someone else define success for you — either directly or indirectly. It’s easy to get distracted by someone else’s bright shiny success story or sexy marketing messages that try to sway you to their vision for your life.

Know yourself and stick to what works for you.

4. Trust your gut.

Again, this is an alignment thing. Advisors and coaches are great (I’m a coach myself!), and it’s still important to trust your gut. In my book, Creative Freedom, I wrote about the five-figure lesson I learned when I surrendered my decision-making to my coach. I ignored the warning signs and feelings I kept getting that something wasn’t right. After all, they’re the expert, right?

I trusted a person whom I thought had my best interests at heart. Someone I thought knew more than I did about my Great Work. They didn’t, and it cost me everything. It took years to rebuild my business and my self-esteem.

Don’t submit yourself blindly to the authority of your advisors. If someone is showing you a path that doesn’t jibe with your instincts, talk about it. Just because they are an expert doesn’t mean they’re always right. Your gut feeling may be your saving grace.

5. Be willing to stand your ground.

This goes for your clients, your audience, and your suppliers. As a creative entrepreneur, you’re building a business built around who you are and what matters most to you. That’s an advantage that distinguishes you from a corporation or multinational conglomerate.

It’s imperative that you are congruent in your work and your word. Speak your truth and honor your boundaries. If you don’t, why should anyone else?

6. Ideas and opportunities are like busses.

As Sir Richard Branson famously said, “There’s always another idea coming around the corner.” Especially if you’re a Chaotic or Fusion Creative (the idea machines of the creative spectrum), you may find yourself with more ideas than you can handle. The sooner you realize that not everything that comes into your brain is meant for you to pursue, the sooner you’ll find peace and be able to stay the course in your creative business.

Creatives are a more open conduit for ideas than the general public, so it makes sense that you might find yourself overwhelmed with ideas from time to time. Knowing which ideas to pursue first is part of being a creative entrepreneur.

Sometimes you get an idea that’s meant for someone else — It’s okay to share it (with or without compensation).

Sometimes you get an idea that’s ahead of its time — It’s okay to save it for later.

You can’t ride every idea bus to every destination. Learn to spot the ideas that are right for you to ride and which ones you can let pass you by.

7. Ride the snail.

After 25 years, I’ve learned that my most productive time for content creation is between Christmas and Valentines Day. I design my calendar to accommodate that. I crank out content like nobody’s business most of the day during Winter, but by Spring, I’m feeling the pull of being outside, distracted by blooming flowers and wanting to be out in the world again, so I’ll get a little bit of work done before lunch, then drag my heels all afternoon.

When my son comes to visit for Summer Break, I’m not interested in creating anything! I just want to play. I want to soak up his youthful energy and have a carefree summer.

Before I learned this about myself, I’d get frustrated with how little I accomplished during the warmer months, and regularly paint myself into a corner with procrastinated projects that still weren’t getting done. I’d force myself to begrudgingly sit down and crank out something — anything — just to meet a looming deadline. Now, I take advantage of my creative ebb and flow and trust myself to know my limits.

As I said in a previous post, “To live as a creative is to be intimately acquainted with heavy mental loads and emotional labor. Even more so for a creative entrepreneur.”

Many of my clients come to the table with chronic illnesses or disabilities that make it impossible for them to work 8- to 10-hour days or 40-hour work weeks. Trying to force yourself to consistently work beyond your capacity is a death sentence.

We all have our own tempos. Honor yours. Learn your cycles and live by them. Do what you can as you are able. If you must hustle temporarily, be compassionate with yourself and recognize that it’s not a permanent state. Give yourself permission to get off the hamster wheel of hustle.

8. Stay in your lane.

This is the first lesson on comparisonitis.

It means do YOUR thing — even if other people try to get you to do their thing.

It’s about trusting yourself and your creative vision. Do the thing YOU are wired for, instead of listening to the “shoulds” of other people. You’ll know when it’s time to change lanes. Don’t weave all over the road!

There’s a time and a place to compare yourself to someone else, and it’s far less frequently than you might imagine.

9. Eyes on your own paper.

This is the second lesson on comparisonitis.

Don’t look to everyone else for the answers.

Do your homework.

Study your industry.

Ask for help from your mentors and people you trust, but when you’re put to the test, it’s YOU that has to show up and do the work. Besides, they may not even have the right answers for you. I can’t tell you how many times I’ve seen someone copy the marketing of someone else, only to discover that it was an experiment that wasn’t working anyway. Ooops!

10. Your business is an extension of who you are.

YOU are not your business. Creative entrepreneurs must build their business in a way that works for their creative type. Until you have a solid team in place, all the tasks of the business rest on you. If you want to avoid burnout, frustration, and overwhelm, you need a business that’s built to work the way that works for you.

Then, as your team grows, you can delegate some tasks and stay in your zone of genius. Believing that the business begins and ends with you, however, means that you’ll stay stuck doing all the things, which is a sure-fire way to stay stuck, stagnant, and stabby more times than not.

Instead, allow your creative enterprise to be an extension or expression of your values and beliefs. Let your audience have a voice (and listen to it). Let your team contribute to supporting that expression. Release your Vulcan death-grip of control and watch your business bloom like never before.

Will there be hiccups? Probably. And you’ll have a much stronger business in the long run.

11. Your goal isn’t always THE goal.

It can be disheartening to work hard toward a meaningful goal, only to have it fall apart or not come to fruition somewhere along the journey.

This is when I remind my clients that your goal isn’t always THE goal. With your limited view of the future, you can only decide to act from a place of what you presently know and what you hope for your future. It’s natural to lean hard on our hopes and “trust the process” expecting that things will work out according to plan.

But you don’t operate in a vacuum. New opportunities and ideas are constantly coming into your field of awareness. Things that you may not have seen, had you not made the decision to move in the direction of your goal. That goal, then, was not a destination, but rather a catalyst to get you off dead center and start moving in the direction that would bring you to a more important goal.

You’re not a failure for deciding to let go of that unachieved goal. It served its purpose. Now you can move forward with your new goal… which still might not be THE goal, but it’s a great starting point!

12. Plans are worthless, but planning is everything.

Eisenhower had it right: Your plans are mostly worthless mere minutes after creating them. As I mentioned a minute ago, you don’t operate in a vacuum. Life happens.

While a plan loses value over time, the act of making a plan is priceless. It’s a skill-building exercise that teaches you better decision making, opportunity costs, and how to course correct when your plan invariably goes off the rails.

The effort and forethought that goes into creating any plan helps you become a better business owner. Your awareness improves and you can see patterns as they emerge. You develop better strategies, and over time, your plans become more achievable.

Planning also helps you right-size your expectations about your what’s really possible for you in a given length of time. During your evaluation of the plan, you’ll identify specific actions that help you move closer to success and identify which actions don’t. That’s one reason annual review posts are so useful. You get to look back on what worked, what didn’t, and make new plans for the new year.

13. If it isn’t scheduled, it’s stressful.

Once you’ve made a plan, it’s not going to be very helpful if you don’t figure out when you’re going to take all the actions required to get you to your goal.

In fact, I developed a step-by-step plan to take my business to $5M in 5 years — and less than a month after I created it, I put it in a box. There were too many steps, it felt too overwhelming, and instead of just doing what I could as I was able, I chucked the entire plan. Five years later, when I reopened that box, I realized my mistake, and set out anew to work that plan. I scheduled the action steps I could take, riding my snail, inching my way toward a multi-million dollar business.

Depending on your creative type, your version of “scheduled” may be less structured than mine (remember to do what works for you!). But some form of scheduling is imperative for every creative. Knowing how much time you have, as well as how much time it takes to complete an action step gives you clarity about what’s really possible for you.

14. You can’t control the outcome.

You can only influence the outcome based on the actions you do (or don’t) take.

Getting fixated on a desired outcome only leads to disappointment when things turn out differently (and false hope when they turn out the way you want!). Ups and downs are normal. Some projects will go extremely well. Better than planned, even. Others will crash and burn no matter what you try to salvage them.

Ultimately, everything in business is a learning opportunity to make better, more empowered decisions next time. With apologies to the band 38 Special: hold onto your Great Work loosely, but don’t let go. If you cling too tightly, you’re going to lose control.

15. Celebrate the actions separate from the results.

BOTH are worthy of celebration. If you only celebrate the big wins, you’re inadvertently programming yourself for hardship and putting undue pressure on yourself to always be “on”.

Since you can’t control the outcomes, it makes sense to train your brain to keep doing the work by celebrating the actions, too. That way, even if things don’t turn out the way you want them to, you can still acknowledge yourself for the effort you put in to influence the outcome. And if things DO go your way, you get to celebrate twice!

16. Mindset is more important than the mechanics.

This is, by far, the most important lesson I’ve learned as a creative entrepreneur. Before Amazon, Wikipedia, and Google, there were encyclopedias, libraries, and mentors to help you figure things out. But no amount of knowledge or logic can overcome your fear.

You have to be open and honest enough to acknowledge that you can’t know everything and still be willing enough to learn and ask for help. (Tweet this.) Especially in the early growth stages of your journey as a creative entrepreneur, the mindset is more important than the mechanics.

Having a growth mindset allows you to see each “failure” as a learning opportunity to improve for next time. In this way, failing isn’t really failure, it’s just useful information. When you’re willing to drop the judgment that says “I already know that” (or “I should be there by now”), and take on a beginner’s mind, you have the ability to see situations, opportunities, and ideas in new ways that can catalyze your growth faster than trying to “make it work” on your own.

17. It can be easy.

Too many creatives I’ve met are trying to work in a pressure cooker. They’re trying to earn a living wage or replace a corporate income without giving themselves enough time to build the necessary foundations that bring business success. Either that, or they’re not keeping their eyes on their own paper, trying to replicate the success of someone else in a way that simply doesn’t work for them.

I’ll tell you what I often tell my clients: you have the magic paintbrush.

You can paint your business and your life to look any way you want.

Even if it doesn’t look the way others expect.

Even if you’re doing things in a way it’s never been done before.

If it works for you and it’s legal, it’s probably fine. You don’t need to overthink it, overcomplicate things, or do something a certain way just because it’s always been done that way. Stay in alignment with what works for YOU.

18. No one is coming to save you.

This is another tough pill to swallow for creatives. You are the boss, so you have to make the decisions. You have to decide your work schedule. Not “you get to,” but “you have to.” If your business tanks, it’s on you to figure out what happens next.

When my business crashed and burned, I had a choice to make. I could either go back to corporate and plow 40 hours a week into someone else’s business, or I could do things differently. Either way, I’d have to invest a good portion of my resources (time, energy, attention, money, and effort) into the work I chose to do.

I invested in me. I built strategically. I hired a team who supported my vision and fired clients and suppliers who didn’t. It was hard; painful even at times. Still, when I realized that the success of my company was entirely up to me, it encouraged me to think like a business owner, not an employee in my own company.

Most people I know go into business for themselves for the money they think they’ll make. Few people I know stay in business for that reason. There’s always something bigger than themselves going on behind the scenes. Because they know that no one is coming to save them they’ve got a fierce focus that helps them stay true to what matters most.

19. You’re a business owner; act like one.

This is the corollary to the last lesson. Running a business is different than having a side gig or a hobby. None of them are wrong. Choose what works for you.

If you decide to be a business owner, however, that means understanding that you’re building something that’s a separate entity from you. You are not the business, remember? It has to live and breathe on its own.

That means at times you’ll be sacrificing wants for needs. You’ll have to make tough decisions to maintain the health and wellbeing of the company. I’ve hired and fired several times in my 25 years as a business owner. It’s never fun to lay off people you’ve come to trust with the vision of your company.

Profit — even a small amount of it — is the lifeblood of your business. Without it, your company struggles to survive.

That’s why so many entrepreneurs don’t take a paycheck in the early years of the business.

That’s why it’s so important that you’re building something in alignment with your values and goals.

When the hard times come (and they come for us all), you’ll be far more resentful skipping a paycheck for a company that’s not in alignment with what you stand for.

20. Be confident, not cocky.

There’s a certain level of confidence you need as a creative entrepreneur to talk about your work with enthusiasm and help people see the vision of what you’re trying to create.

When that confidence rolls over into arrogance, you run the risk of causing real harm to your clients. No one is perfect, and to position yourself as the be-all-and-end-all to your market is only setting you (and probably them) up for failure.

Remember, ups and downs are normal. Pretending you’re above them is not.

21. Like attracts like.

Not to get too woo-woo here, but there’s a kind of Karma in business. If you’re cranky with your clients, you’ll attract clients who are cranky. If you’re generous with your clients, you’ll attract clients who are generous.

I can’t tell you how many people I’ve met that complain that they’d never pay “that much money” for something and then wonder why they can’t attract higher paying clients themselves.

In the world of creative entrepreneurship, what goes around comes around.

22. Be willing to invest in yourself.

This is a corollary to the previous lesson. I don’t think that it always takes money to make money, and I understand that you don’t always have the money to invest. But that’s not the same thing as being willing to make an investment when the resources are available.

At one point in my career I had less than zero dollars to invest, but I had time, energy, and know-how that I could invest. My willingness to do what I could as I was able created an opportunity to work with someone who opened doors for me and created an opportunity that changed the course of my business.

Remember, money is only one kind of resource you can invest. Being willing to make an investment in your growth opens doors to a lot more opportunities.

23. As a creative, the most important “product” your company has to offer is YOU.

When I worked exclusively with direct sellers, I would tell them, “You are the only product that goes with you to every event and you’re not listed in the catalog.”

Again, you are not the business, but you represent your company everywhere you go. People buy into who you are, what you stand for, and why you do what you do. The image you craft, the story you tell, and the brand you build hinges on YOU.

24. To each their own — don’t take it personally.

You are not everyone’s cup of tea. Not everyone will agree with you. Not everyone will like you, no matter how agreeable you try to be, no matter how much you try to twist and contort yourself into a mold of someone else’s making.

Some people will adore you no matter how much you goof up. Some won’t. So what? They are not your right audience. Let them move along so that you can focus on the people who are precisely right for you.

That’s not an invitation to be a jerk or cause harm. You still have a responsibility to be a good citizen of service to your audience. But it is a reminder that you can’t serve everyone and you have the ability to build your business in a way that works for you, even if it doesn’t work for somebody else.

25. It’s not magic. It’s marketing.

This is not the Field of Dreams. If you build it and don’t market it, they will not come. That movie (and that line) have done more to set creatives up for failure than anything else I’ve seen in my 25 years online. It is both a blessing and a curse.

On one hand, I agree with Steve Martin. You want to “be so good they can’t ignore you.” And yet, being great means nothing if no one knows you exist. If you paid attention to the movie, you’d remember the months of effort Ray Kinsella put in long before the ghost of Shoeless Joe arrived from beyond the corn. Ray was on the verge of losing everything before his daughter suggested they might generate an income selling tickets.

Marketing works wonders, but isn’t magic. If you build it and don’t do the work required to let people know about it, you might as well quit before you start.

Ferris Bueller was right. Life does move pretty fast. 25 years came and went in a blink, took no prisoners, and taught me a lot of lessons in business. These are just a few. (Tweet this.) I hope they serve to shorten your learning curve on your entrepreneurial journey.