25 pearls of wisdom that will help you survive (and thrive) during the peaks and valleys of your career. Whether you’re a full-timer or freelancer.
Nobody has mastered all of the following principles. It’s likely impossible. But the more you follow, the better you’ll be. If I had the chance to sit down with my 24-year-old self, 24 years ago… this is what I would say.
1. Crowd surf.
Nobody is a born master. It takes time and effort. More than you think. It might seem obvious that you must master your craft to be successful, but most people aren’t intentional about it. They punch out at 5 and spend the rest of their time vegging. Study any top sports star, musician virtuoso, or bestselling author. They’ve all spent thousands of hours toiling to become great. Like 2, 3 and 4 X the amount of time that everyone else spends. Want to be the Pai Mei of your world? Be prepared to grind. But don’t stop when you think you’ve become the master. Keep going. You must evolve your skills (and your tastes) over time. Do this and you’ll always stay above the crowd.
2. Hack brains.
This is the second most important career principle to learn after becoming the master of your craft… study psychology and learn how to sell. Read books on salesmanship and negotiation. Learn to communicate effectively. It changes the game. No matter what you do, you must collaborate with co-creators, deal with bosses, and present to clients. What good are your brilliant ideas if you can’t persuade people to buy them? Many books have been written on this subject. Go read some. (See the 'Survival Kit' at the bottom of this post.)
If you only take away two things from this post, take these two above. If you want more, read on.
3. Water the plants.
It’s absolutely imperative that you maintain a healthy network by keeping your professional contacts fresh. This is especially difficult if you’re an introvert like me, but you must try. People will phase in and out of your professional life, and some will go onto bigger and better things. If you keep those relationships alive, it increases your chances of working with them again. Most all of my jobs have come from referrals. If I didn’t have the contacts, I wouldn’t have had the referrals. And I’m not alone, most of my creative friends and colleagues say the same thing. Build your network and feed it.
4. Spread the love.
Strive to be generous and give creative referrals wherever possible. Think of it as paying it forward. This is especially helpful when freelancing. It might seem counterintuitive, since you are, after all, a competitor to other freelancers. However, creative colleagues and recruiters are likely to reciprocate if you are generous and helpful. And it creates good karma. Try it. It works.
5. Be the oxygen.
Become indispensable by always overdelivering. When you deliver more value than other people, you leave a lasting impression. On the few rare occasions that I have failed to follow this principle and simply “phoned it in,” I robbed myself of repeat business. And you never know who you might impress by overdelivering. Even if they seem insignificant at the time, people move up and never forget the impressions you leave behind.
6. Don’t masturbate.
When you have downtime, resist the urge to just watch movies or play video games. It might be fun, but strive to do something creative and useful. Work on your book, screenplay, film, mix-tape, blog, painting, or whatever. You’re a creator, so create. Especially if you’re not getting real fulfillment from your weekday job. You’ll feel more fulfilled in life and you’ll thank yourself later.
True, it’s important to decompress once in a while, but try to keep it in measure. My friend Rich Siegel puts this way: “Say something incredibly rude on Facebook [and] get yourself booted from this awful time suck. And spend that time doing useful things, like cold calls, networking and book reading.”
7. Quit often.
It’s tempting to get comfortable in a full-time job, especially when you’re making good money. That’s why they call it The Golden Handcuffs. I’ve learned this the hard way. But if you’re not moving, growing and challenging yourself, you’ll eventually become irrelevant. And when you do finally get laid off—and it happens to just about everyone—nobody will want you. However, if you move around often (maybe every 3-5 years) then you’ll create more diverse experiences and more diverse relationships. Which is only a good thing.
8. Build a war chest.
It’s surprising how few people actually save money. Like my friend, Susan Alinsangan says, “Nothing gives you confidence, composure, and self-assurance like being backed up by substantial savings.” And Rich Siegel put it like this, “With a grab bag of invoices and checks it’s easy to lose track of time and money, which by the way are the same thing.”
Living on the financial edge makes you more likely to make bad career decisions out of desperation. Don’t make that mistake. Be disciplined and create a cushion. It helps relieve anxiety.
9. Don’t be a D-bag.
As my friend, Chris Pouy says, “It’s not easy in an industry with fragile egos and big personalities, but if you’re mean, disrespectful or rude to the people you work with then you’re doing it wrong.” I couldn’t agree more. “If you need this explained to you, go ask your mom,” adds Alinsangan. Being a jerk might have propelled careers 50 years ago, but not anymore. Even if you’re a brilliant jerk. As Reed Hastings said, “Some companies tolerate them. For us, the cost to effective teamwork is too high.” And that sentiment is spreading. So if being a jerk is part of your stock and trade, be prepared to become a fossil.
10. Remember family.
Got a husband? A wife? A family? A dog? Susan Alinsangan says, “At the end of the day, family is who you go home to. Not your ad buddies. Hopefully, they go home to their own families.” It’s true. Why you’re 80, you’ll scarcely remember your professional triumphs. By then, your personal relationships and human connections will be what matters most. Don’t let those die in pursuit of fame and fortune. Or you’ll be pretty lonely sitting on that pile of gold and award show medals.
11. Vacate.
Whether you live to work or work to live, take a vacation. Often. The mind and body need rest. And your family needs quality time with you. In a study of deathbed regrets, the second most common regret was working too much at the expense of family and relationships (especially for men). Don’t make that same mistake. When you’re old, it’s irreversible.
12. Try to click.
If you work as part of a creative team, be a good partner. Alinsangan adds, “If you’re one of those people who are so awesome you don’t need a partner, this doesn’t apply to you. But if two people decide to be good [creative] partners, it’s crazy fun and sometimes great work happens.”
Being a good partner means not only respecting each other but creating a safe space for bad ideas. Open and frequent dialogue is a major pathway to idea creation, but if you’re too embarrassed to share a bad idea, you’ll get blocked up. Think of bad ideas as fertilizer. It stinks but helps things grow. Bad ideas can inspire great ones. Don’t discourage them. Just put them on paper and move on.
13. Have an exit strategy.
“In case of fire, you should always have one when you move into a new home… and when you get a new job, in case of disillusionment,” says Susan Alinsangan. I concur. Try to keep your portfolio up to date. It’s your parachute. And keeping your professional network fresh is like another parachute (see #2).
14. Prepare for feast and famine.
Many things in life are cyclical, constantly going up and down. Be ready. Chris Pouy says, “Especially if you’re a freelancer or thinking about going freelance… be prepared to endure the ebb and flow. The highs are high (you could make a down payment on a house) and the lows are even lower (dipping into your Roth IRA.) Prepare accordingly, mentally, emotionally and financially.”
Don’t just blindly traipse through life, living in the moment, thinking that flush times will last forever. They don’t.
15. Pick your battles.
“If you argue with everyone all the time about everything then when you really need to lay on your sword it will turn into aluminum foil,” says Pouy. “Plus everyone will hate you. Choose your moments carefully.” I can attest to this truism. It’s particularly true if you’re a freelancer. My friend Tony Stern once said, “Freelancers are hired to be the aspirin, not the headache.” So spar sparingly.
16. Go wide angle.
Even though mastering a single skill is paramount, that doesn’t mean you can’t broaden your skillset. Are you an art director? Dabble in graphic design or animation. Are you an advertising writer? Dabble in blogging or screenwriting. Are you a photographer? Dabble in filmmaking or VR. You might just discover that you’re good at multiple things, which not only opens other doors but creates some variety in your life.
17. Niche down.
This might seem completely contradictory to point number 16, but it’s not. Whatever your primary mastered skill is, find a way to niche down by specializing in a distinct style.
For example, let’s say you’re a graphic designer. It’s tempting to have an eclectic portfolio because we all have multiple interests and we instinctively want to appeal to a mass audience. But it’s a mistake. An eclectic portfolio makes you appear dispassionate and unfocused. Find your niche. Maybe you’re into retro vector-style geometric design. Maybe it’s ornate, Victorian-style design. Maybe it’s an urban street-style design. Focus on your favorite, then strive to be known for that style—first and foremost. It will make you stand out from the rest.
Doing this doesn’t mean you’ll necessarily become typecast. People reinvent themselves all the time. Think of your creative career as chapters or seasons, each with its own dominant and distinct style. Unless of course you only like one style of art and have no interest in evolving. That’s fine too, as long as you master that style.
18. Exploit the internet.
There are so many ways to monetize your creative skill set. You don’t have to give away your work for pennies on Fiverr or similar race-to-the-bottom platforms. There are other platforms to publish your creations. Etsy, Amazon, Redbubble, Shutterstock, Teachable, Envato, Musicbed, YouTube and many more. Or build your own platform using Shopify or Wordpress.
If you’re not creatively fulfilled with your day job, or you’re tired of being poor, give it a go. But start soon because it usually takes at least 2-3 years to see some return on your investment. Who knows, you might just strike lightening. (There are podcast episodes explaining how to do it, by people who have done it. Look for them.)
19. Raise your prices.
Many people are under the impression that charging lower rates will create more opportunities. But it’s simply not true. Research repeatedly shows that there’s a direct correlation between how much something costs and its perceived value. And when you’re perceived to be more valuable, you’re consequently treated better by an employer or client.
In simple terms, the more you cost the better they treat you. And you’re worth more than you think. The photographer Chase Jarvis shared some valuable advice on this.
If you’ve been honing your craft and selling in your marketplace for 10 years or more, you could definitely be charging more. Especially when you consider there’s only one you.
If what you do is an un-special commodity, you may be the exception. So break free and de-commoditize yourself by specializing and mastering in something.
20. Tool up.
Creative apps unleash superpowers. As a visual storyteller, I’ve expanded my toolbox from mere desktop publishing apps for graphic design and layout, into animation, video editing, music production, and film production. I may not be a master at all of them, but I now have the capability to singlehandedly bring ideas to life—into finished form. And then publish it on the internet. It feels good. Creative tools can help you make massive leaps. This was a key selling point for Apple by Steve Jobs back in 1980.
21. Enjoy the ride.
It feels amazing to create for a living. Even on the bad days, creative jobs are more fulfilling than most. But don’t take things too seriously. You’re not curing cancer with your art. So have fun. Bring some levity to work every day and spread the joy. Create a lighter environment. Fill the room with dopamine, oxytocin, and serotonin—through levity and positive social interactions. It will inspire more creativity and better ideas. Whereas cortisol—the stress chemical—kills creativity (and eventually you, for that matter). I was reminded of these truths when I heard about film director, Taika Waititi, on the set of Thor: Ragnarok. Apparently, everyone loved working with him because he made the experience fun and casual. And who could argue with the results?
22. Be humble.
Snobbery and egotism is a real problem in the creative world. Sometimes artists think they’re being discerning and confident, but they’re actually being arrogant and offensive. And think of this: even the most brilliant creatives strike out once in a while. Every well-known movie director has made some stinkers. It happens. And it happens most when we become overconfident from lack of humility. Unless you’re sitting on a mountain of cash and can afford to piss off everyone, lose all your friends, and never work again—be humble.
23. Boss you.
You might just be the world’s worst boss. Why? Because, as Seth Godin said, “Even if you’re not self-employed, your boss is you. You manage your career, your day, your responses. You manage how you sell your services and your education and the way you talk to yourself.” I love that. You are culpable for the outcome of your career. Not someone else. After all, you control your own destiny. So being the best boss ever is as simple as striving for mastery and not compromising in life.
24. Accept reality.
The world isn’t fair. Life is hard. And good guys never win. That’s what your inner cynic might try to convince you. But it’s all a lie. The reality is if you’re living in the free world, have an internet connection and a credit card, then anything is possible. The sky is truly the limit. Nothing is holding you back, except you.
Broadly speaking, there are two kinds of people in this world: (1) those who believe external powers control their destiny, and (2) those who believe internal powers control their destiny. Your success depends upon what you believe. Like Henry Ford said, “Whether you think you can or you think you can’t, you’re right.”
25. Believe.
We all have self-doubt. In a study of top CEO’s, the vast majority of them suffered from imposter syndrome. For creatives, it’s natural to question your own judgment at times (personally, I think it’s healthy). But you must believe in your own subjective tastes to succeed. It’s what makes you you. But then you must also equally accept others. As the famous artist, Jeff Koons, “The journey of art starts with self-acceptance—the subjective. Once you accept yourself, you are able to move on to the objective—the highest state—which is the acceptance of others.”
Thanks for reading. Please see the 'Survival Kit' below. And feel free to leave a comment or add something that you think I left out.
Footnote: For more juicy nuggets, read this post by my friend, George Tannenbaum.
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SURVIVAL KIT:
The following 8 books should be required reading for every creative person, regardless of discipline. They are timeless. They helped change the way I think about creativity, salesmanship, audience-building, and life.
by Chris Voss
by Sally Hogshead
by Steven Pressfield
by Seth Godin
by Seth Godin
by Paul Arden
by Paul Arden
by Ryan Holiday
Enjoy.
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Note: There are a few affiliate links in this post. Things I recommend. I’m paid a small referral fee if you happen to click and make a purchase (no additional cost to you of course.) Thanks for clicking!
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