How to Do What You Love And Get Paid Well For It: 5 Keys


My post on How to be a Professional has been by far the most popular post on this blog. So I thought I’d expand on that after getting asked to speak to high school students at our local career tech yesterday and repurpose for you here.

So I’ve got five basic keys to share that I believe if you do these things, you’ll be successful in your WORK, whether you go to work for someone else or start your own business.

1. Start with Passion

It all STARTS with passion — a fire burning inside of you about something. Passion is typically easily identifiable. You ooze energy, excitement, devotion to a cause or subject.

A passion is about a chase, a quest, a never-ending hunt. And sometimes, if left unchecked, it’s an all-consuming obsession.

Passion about something moves your soul when it is expressed in your life. It is focused joy and love for a subject. A passion blocks out the world or time (and sometimes people) for the chase.

You follow it, follow it, follow it … running without exhaustion after it … until you find yourself LOST in it.

When you emerge from it …. you ask yourself:

How is it really 2 a.m. in the morning?!
When was the last time I ate?!

Been there before? I have hundreds of times.

Passion is dreaming and wondering about when you can continue the chase to the neglect of most everything else. A passion in work is matched usually with some foundational NATURAL ability or interest or curiosity.

One of the most difficult things we’ve found as a business is finding people with DRIVE and INITIATIVE that typically is birthed out of genuine passion for what we do.

For me, it was writing. I loved to write. I loved to express my inner thoughts for the world. I loved the effect it had on people (and still do). My first published writing was a Letter to the Editor of the Lone Grove Ledger. And last year I got to see my name on the cover of a commercially published book! But mostly my writing passion now expresses itself as BLOGGING. It’s one of my life passions and I’m always seeking ways to use and refine it.

You should actively start seeking to DISCOVER what your passions are NOW … and it’s likely you’ve unearthed some of them already or on the path to finding and exploring them.

Here’s some thoughts on how to find your passion:

  • Try lots of different things out — you need to take a lot of things out for a test drive and see what invokes the chase.
  • See what sticks and resonates — see what causes a spark that lights a fire in you.
  • Ask for some direction — ask others what they see in you and potential ideas; be around people who love what they do.
  • Watch for the tractor beam — passion pulls you in … be alert to that gravitational pull.
  • Be patient — it just take time to find things you really like … I’m still finding new things I love and draw me in!

And then when you find those passions ….. hold on to it. Seek it out. Fan the flame. And make a bonfire of it!

Side note of career or professional advice: Potential employers, including myself, and prospective clients look for passion and enthusiasm about what you do. We want to know you have that fire about the role you are looking to fill with us or the work you’re going to provide for us. We want to see HUMBLE, focused passion for the work you do!

2. Sharpen Your Sword

In your work, you need to pair that passion with actual SKILLS that allow you to get paid to do it every day. People pay you money (whether with a paycheck or from an invoice) because you have a skill that adds value to their life.

Think about the value you offer others now. It’s often the skills — whether a great sales personality, or the ability to build software programs — that add value — more sales, more revenue … or helping customers save time and money with your software.

Think about the reasons you pay others money. In the past I have paid a real estate agent to sell my house (and to buy ones as well). I am interested in their skills of knowing how to negotiate contracts, knowing the neighborhood and knowing potential buyers. Those things go back to skills. They have a skill of understanding the legalities of real estate contracts. They have personal skills related to knowing people. They have spent time honing their skills of the neighborhood, how houses are contracted, what to look for in bad and good houses, etc etc.

The skills I developed initially with web design — like learning CSS or HTML so I could build cool websites — allowed me to get paid to follow my passion.


And your work should be your craft and you should be dang proud of the work you do in your craft. Your work is a display of your unique gifts and talent to share with the world.

And if you align your passions with skills …. you get PAID to do what you love!

By the way, you can be passionate about something but not get paid …. but that’s called a hobby.

So here’s how to hone the skills within your passion to get paid to do it:

  • Build upon previous skills — start with a simple set of skills and add to them, bolster them, build them up
  • Always be adding more — you must always be looking and acquiring new skills to build upon your other skills or else you’ll get left behind
  • Always be learning and growing — just because you’ve mastered one skill doesn’t mean you should stop honing it or developing and mastering others
  • Always be searching for new skills to acquire — look for innovations, what’s new, what’s emerging that will set you apart and what people value most
  • More skills = more money — employers and potential clients value people with great skill sets to lean on and utilize and we pay a premium for it
  • Skill acquisition isn’t necessarily about a piece of paper — just because you have a degree or a certificate doesn’t necessarily mean you know how to do something; relying on paper alone is a recipe for disappointment

In our business and on the web, technology changes faster than the speed of light and competition is always increasing and getting better. We must always be learning new things …. and enhancing previous skills to stay up to par for our customers.

For our team that means learning new technology, like HTML5 or understanding emerging concepts like Responsive Web Design and being on the cutting edge and be thought leaders of those who utilize it. (Or whatever it may be.)

As a side note … let me say … if you stop learning that’s what I call being plateaued. In the medical community they would call that death. I kind of do too.

You won’t be spoon fed new skills by employers or clients. You’ll have to actively engage in learning new skills and building on others and actually put your life in drive.

So keep getting better and better, adding more and more skills in your arsenal.

Here are two general ways that I’ve seen personal success in adding skills:

Master the TOOLS of your craft

For people in our business typically that means mastering software or code. Software like Adobe Photoshop or code like PHP or Ruby on Rails.

Make sure you:

  • Know them inside and out, backwards, forwards
  • Get fast and efficient at them
  • Learn all the shortcuts
  • Stay ahead of what’s coming next with those tools — subscribe to the blogs, magazines, whatever you can to learn the latest tricks of that software

I got several jobs in my previous career because I knew and mastered one particular software application. What is it for your field? Seek those tools out and start learning them to add it all to your skills vault for your craft and passion.

By the way, for almost every professional … I highly suggest learning the software known as Google. Meaning specifically … learn how to Google to get the answers. It is a GREAT way to learn. If you have a question, Google probably has the answer. There’s probably a video tutorial on it, or a content-rich site about it … and Google can help you find it.

Google is a troubleshooting tool. It can even add, get the weather, and tell you the local time in Dubai.

Next, learn from the Masters of your craft

Find someone far far ahead of you and seek out their help and ongoing counsel. Be their apprentice, even if it means not getting paid! For a lot of people that means interning, or doing whatever you can to learn at the feet or in the shadows of some of the best in the business. I have frequently bought lunches and coffee for those I’m seeking advice and counsel from (although that’s not even a fraction of the value I get back out of it).

Find, follow and study the best in your field. Ask them how to get started and get better

Don’t just be inspired by the best … be MOTIVATED by the best to be better.  Don’t be intimated or give up because of how far ahead they are – those people spent YEARS and YEARS honing their craft, sharpening their sword, failing and learning and picking themselves up. They are the best because they didn’t give up!

There is no such thing as an overnight success. And it’s been said that it takes 10,000 hours to master success in a skill or field. I did some math and I’ve been doing this (startup entrepreneurship) for over 4 years now. At a minimum of 60 hours a week on average (and that’s on the low end), I’ve got around 12,000+ hours in this field.

And guess what? I still feel I’m not where I want to be. I’m not the best. I’m not even close.

I’m not even the best I WANT to be. I’m still chasing excellence with each and every step.

NEVER ever ever stop learning. Never settle for today’s best … or worse yesterday’s. That’s the path to complacency and mediocrity. And I don’t want to use the time and talents I’ve been given (and fostered) doing half-ass work.

Trust me … there will always be someone better, faster, even smarter, and often more naturally gifted than you. There is always be something new to learn.

So be on a lifelong quest of learning and applying that learning. Be a craftsman always sharpening his sword each and every day.

Honing your skills takes a lot of hard, consistent work. It ain’t easy. This is why I started this discussion with passion. That all consuming devotion to what you do will help keep you going when the crappy times come (and they will). Your passion drives your desire to learn more about it and to master it or seek to master it every day.

3. Seek Out Wisdom and Guidance

You need to find mentors and advisors in every facet and walk in life, not just your field … to walk with you.

I love having mentors and advisors because I get to learn from their pain and mistakes … at a fraction of the cost they paid to go through it.

My mentors are my counsel of elders for living a life of purpose and passion. I want people who have rich and diverse experiences and expertise … who graciously give it ALL away to me. I want mentors who want to leave a legacy within me.

Mentors are truth tellers. They aren’t like my mom who likes everything I do on Facebook. (Sorry Mom!) They don’t sugar coat the truth just to pacify your ego. They simply want the best for you.

Mentors help you see your blind spots as they help you get perspective. They are partners for life ….

  • Sometimes they pick you up.
  • Sometimes they pull you back down to reality.
  • Sometimes they put their boot in your butt and a fire in your pants.
  • Sometimes they walk beside you through the dark and scary times ….

Here’s how to find a good mentor:

  • Identify, then observe potential mentors — see how they act when no one is looking. Now I’m not talking about stalking them. Merely observe how they act toward and around others
  • Make sure they deserve to be your mentor — do they have an ego to be fed by you, or are they looking at multiplying their influence in the world through you
  • They must first and only want your ultimate best — mentorship is about legacy, not selfish gain or ego
  • Buy lunch or coffee on their terms — after you’ve identified someone you want to potentially be your mentor, seek out the easiest way on them to speak one-on-one. Don’t assume they have time to spend an afternoon with you. Work around their schedule.
  • Start by asking them questions and heed their advice with action — show them you are willing to act and move on their advice
  • Good mentors are teachers … who are learnersI’m not talking about educators, I’m talking about those who are actively seeking to get better and willingly sharing it with others. Good mentors pass it on and pay it forward.
  • Again, respect and value their time!

The last parting thought about mentors is this … one day when you get ahead … commit to BE a mentor to someone else who asks!

4. Get Experience by Having Experiences

Next you also need EXPERIENCE … and EXPERIENCES. This is about USING your skills and passions in the real world. I want to see people who have been under “live fire” conditions — not simply someone who has sat in a classroom and learned the theory about it.

Live fire experience can also be baptism by fire. Being thrown into a situation and being forced to make the best of it. I love those experiences. I want to see how people will act and react. How will they work if they don’t have guidance? Or what if they don’t have all the tools they need? What will they do?

I want to see people who have had real live experiences like this.

This is why I like to throw our new developers into a scenario where they are forced to learn and get better … and typically that means pushing them to get their first theme or plugin out as soon as possible. (And trust me, when you put a product out that potentially thousands of people could hate, you get immediate feedback and are forced to learn on the fly.) After their first one — whether that fail, flop or fly — they are initially battled tested and through this process we learn a lot about them as they do themselves.

In college, I was frustrated by many of my friends who were 10 times smarter than I was, but who worked at Taco Bell at night. I thought it was a waste because they could make the same money working IN their field doing similar duties (yes, like taking out the trash).

Sometimes the best way to get those are by pro bono work (or dare I say free) in their field like an internship.

Needless to say you need a set of DIVERSE experiences so you also know what you like and don’t like.

Here’s some ideas for getting experience and experiences:

  • Start somewhere, anywhere you can — At first, take what you can get and opens up to you. But try a variety of situations and work opportunities if you can (with the note of saying don’t job hop simply to job hop – leave every place you worked at better where your boss would want to hire you back)
  • Doing free work at first — Yes sometimes you have to give your time away
  • Get an internship — Not enough young people seek this out while going through formal education. That’s a waste. Even if it means answering phones or taking out the trash for a company doing work in the field you are most interested in. It’s a step IN the door that’s often the hardest.
  • Doing the grimy sucky work of the craft — This could mean taking out the trash, or perhaps cleaning the bathroom. New team members here typically get tasked with fixing bugs and helping in our support forum. It’s one of the most valuable things we do for our customers but perhaps the hardest job in our business. If you survive and thrive in that, you’ve earned other opportunity here. It shows you want to be here and will do whatever it takes to make progress!

Let me give you an example of how I’ve done all of this:

I’ve helped my dad bag minnows in one family business and charged customers for it on Saturdays when other kids were out playing. I’ve swept floors, cleaned motorcycles, worked under the most hard-working, never-let-you-sit-down uncle in another. I’ve worked a state park job where I mowed (I’m asthmatic and have bad allergies) and worked with convicts.

While in khakis and a polo shirt at several jobs, I helped move furniture in the heat or other “manual labor” tasks others wouldn’t dare do in my spot … without complaint. I wanted to show them I was a hard worker and would do the work that needed to be done.

At almost every job, I noticed when my bosses came in and made sure I matched or exceeded it. I’ve also worked under terrible, mean-spirited, micro-managing bosses while being underpaid and underappreciated … but still gave my full day’s work to them and everything that asked of me.

Along the way though, positively, I gleaned a bunch of amazing contacts from people who sought to work with me (because I put in my time and gave my full attention to my job, seeking always to get better). I’m confident all my bosses would have hired me back. I sought to leave every job better than when I started. I also sought in each position — from the internship and jobs I held in college that helped me boost my career — to learn as much as I could from anybody willing to teach me.

By the time I started iThemes in 2008, I had held over 13 different job since I was 16. I knew what I liked, didn’t like, hated and LOVED. I had a wealth of experiences to bring into my new job as a full-time entrepereneur.

  • You need to figure out what you DO and DON’T want to do. How you are best suited to work. What your strengths are and your weaknesses.
  • You need to see how workplaces function.
  • You should work in a big company and a super small startup or maybe something in between too if you can.
  • You need to figure out how to be a professional and you do that by watching the real true pros.
  • You need to learn the difference between reality and idealism.
  • You need to learn how people value your skills … what price they assign to them.
  • You need to know how money works — you need to see how money is made …. not just on a paycheck but how client work translates to revenue that provides for the paycheck.
  • You need to see the bad, good and downright ugly — all of it.
  • You need to watch and observe how others do the job you want to do — and how you can be even better!

Otherwise how will you know what’s really really good … or just disgusting awful?!

That’s one of the painful parts working with young people like we do (the average age of our team is about 27-28 or so): They don’t know the difference!

Experiences are simply water markers to gauge perspective and success in the future. They are case studies to fall back on.

And along the way of having these priceless experiences …. BE SURE to document the experiences in your field, following and chasing your passion …. so you know what you want out of it!


So now …. if you have and are doing all of these things above — seeking passion, acquiring skills, gleaning wisdom from others and having diverse learning experiences … you are RIPE for opportunities to come your way.

Passion + Skills + Wisdom + Experiences = OPPORTUNITIES

I think those are necessary ingredients and prerequisites to not just starting a business … but living a life of purpose that makes a difference in the world … in your work!

Get and develop those things …. and trust me … opportunity will come.

Sooner or later, if you’re good and getting better … honing and mastering your craft …. collecting experiences and connections …. seeking wisdom from those with more experience and expertise … WHILE doing right by people …… there will be a glimmer of opportunity present itself to you at some point.

Do the first four and keep doing them … then be READY that opportunity.

All of this has been about building up to get that opportunity … to be READY FOR IT. So that when the opportunity presents itself …. you can jump in, hit go, push publish, launch, dive in.

I tell people that I was at the right time, at the right place … and I was READY for iThemes.

I was 31 years old when the opportunity to start iThemes opened to me. I spent the better part of my life building momentum, skills, experiences, connections … for THIS opportunity. I was impatient and ever frustrated. I used it all as wood for my fire to do what I have done since 2008. I channeled all of it …… for the events in 2007 and 2008 so that I could seize the opportunity that opened to me.

I like to use SURFING as an example for this. Surfers swim out into the ocean and wait and watch for that “big wave” … the perfect wave to come in. But what if the big wave comes in and they don’t know how to get up on the board?!

What if they haven’t honed their skills to ride that wave? What if they are on the wrong beach and haven’t sought out the veteran surfers to see where the best waves are?

The goal is to BE READY for your opportunity. And to do your homework and practice to find something that you love so much, and can be so dang good at … that someone will actually PAY you to do what you love each and every day.

So here’s my final word to you ….

The world needs you.

We need you.

I need you.

We — the watching world — need your gifts, your talents, your skills, your passions expressed through the unique lens of your life.

We are waiting for you to bloom and blossom and to share all of this awesomeness with us — whether it by through starting your own business or as a professional in your field.

We want to see the one-of-a-kind creative display of who you are and what you have to offer the world ….

So again ….

  1. Find and follow your passion. Stoke the fire for your craft.
  2. Don’t give up on learning and being better. Stay hungry for more.
  3. Learn from the wisdom and experiences of others in order to go farther
  4. Seek out your own experiences of the world to gauge it all for yourself
  5. Then be on your toes and not on your heels …. READY to jump at what opportunities present themselves.

We are waiting for you …..

So here’s the deal ….. My question and challenge for you is this …..

What’s the NEXT step you’re going to take TODAY? To move forward your life and dreams forward.

Let me know how it goes!




  1. sounds like we have similar backgrounds. …i certainly remember the days of having to do the hard work that no-one else wanted to do. i think that’s one trait every true entrepreneur needs to have — be willing to put in the time and the sweat. the “dirty little secret” to living this dream of getting paid to do what you love is that it starts with really, REALLY hard work & sacrifice.

    you also hit the nail on the head in never being satisfied with where you’re at. always push. always strive. always be looking for the next hill to climb. i found over the last year or so that i was not passionate anymore about what i was doing. and so i was not caring about learning or becoming better at it. guess what? Plateau! and that’s a bad place to be. i found where i wanted to pour my time passion and shift my focus and now i am much happier, because i am learning something new every day. inspire and be inspired. 🙂

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