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How To Find Work You Love As A Creative Entrepreneur

Matt K Head
MATT K HEAD My Creative Calling Steve Jobs 2 Work You Love 2023-05-26

MCC #57 – 26 May 2023

Welcome to My Creative Calling!

We’re continuing with part two of my Steve Jobs series for creators:

  1. The creator journey
  2. A creative business you love
  3. Death as a motivator

Today we’ll be exploring some business insights from Steve and applying them to creative entrepreneurs, with a focus on cultivating work you love. 

I don’t know about you, but I am tired of all the generic AI drivel content.

There has been an explosion of crap in recent months.

Some of the worst are those AI-generated comments summarising creators’ posts. 

Who wants to see that?

So what you get here will not be another:

No, this will be different. 

It will have a human perspective, tell a few stories from experience, and draw out some actionable lessons.

I’m experimenting with my writing and trying to carve out my unique voice that doesn’t rely on AI to create the meat and potatoes. 

Sure, AI helps with things like idea generation, outlining or grammar, but I don’t want it to replace my creative brain.

And I hope I can inspire you to stay true to forging your own path, with your brain holding the reigns. 

So buckle up, and let’s get into it.

What I Learned From Steve Jobs Part 2: A Creative Business You Love

Invest in yourself and start building your dream

Are you sick to death of ignoring your dreams?

Your tired of putting them on hold?

Waiting for someday, which we know never comes.

I finally reached the point where I had it with all my BS and excuses. 

It was time to start taking action.

Those dreams aren’t going to build themselves.

And we aren’t getting any younger.

The commitments and obligations keep piling up.

If we don’t make time for this, it won’t happen.

It’s incredible what we can pull together when something becomes a priority.

If you asked me two years ago, why don’t you write a weekly newsletter?

I would have said, “I don’t have time.”

But the truth is I did have time.

In fact, it was probably the best time I would ever have had (before I had a child to worry about).

But all I could see was the reasons why I couldn’t start.

So I challenge you today to start looking for why you CAN start that thing you have been putting off.

If there is one thing I have learnt about running a creative business, it’s that ACTION is king.

Those who take action reap the rewards.

You don’t even have to be the best.

While you sit around feeling stuck about creating a website or worrying what your peers will think of you, some other hack has simply started writing online promoting their terrible offer and is getting clients. 

You have to START.

And over time, “better” will come.

If you keep showing up.

So my first point today is inspired by Steve Jobs’ entrepreneurial enthusiasm and the birth of Apple.

Legend says that Steve and his friend Woz famously started the company in his parent’s garage. 

Humble beginnings for what would later become the world’s most valuable company.

It goes to show that everything starts from a simple dream or idea.

Who knows where that thing on your mind could lead?

It could change the world.

The sky is the limit. 

But you will face challenges in trying to bring that idea to life.

Those challenges may come mainly from those close to you (family and friends) who try to protect you from failure by encouraging you to play it safe.

When my partner, Steve Wozniak, and I started Apple, most of our friends and our family told us we were nuts. 

Woz had a great job designing handheld calculators at Hewlett Packard and I had a fun job designing games at Atari.

And we were giving them up to start this company to make a primitive computer on a PC board that a handful of hobbyists, mostly our friends, might buy for less than it costs us to make.

Steve Jobs

It’s one of the most difficult things to deal with.

You have this idea you have been brewing for a while.

You’re tremendously excited about it.

You’ve thought it all through from end to end.

“This could be big,” you think to yourself as you nod up and down with a little smile on your face.

You excitedly tell your partner.

They kind of go, “Yeahhhhh.”

You can tell they don’t get it yet. But that’s OK. They love you and want you to be happy, so you know they will support you at the end of the day. 

But then you tell your parents.

“I don’t know about that,” they exclaim. “What about your career? You would be throwing all that hard work down the drain.”

Then you tell your best friend, and they respond:

“Dude, I admire your enthusiasm. But that’s crazy!”

You can tell they don’t want to shut you down, but they don’t get it.

Only you can see what you see.

So now you’re in a pickle.

Do you back yourself and go for it?

Or do you follow the well-intentioned advice from those who love you?

Well, here’s what Steve did:

I remember talking to Woz, and saying:

“We may fail, but we have no responsibility now, no wives, no kids, no house payments, nothing. If we don’t do this now, we never will. We have nothing to lose – the worst we’ll get out of this is that we’ll have the memories of having gone for it.” 

So rather than invest in better cars, or better apartments, or our bank accounts, we decided to invest in ourselves.

Steve Jobs

They went for it!

But they were young, just out of school with minimal commitments.

As Steve rightly pointed out, it was the best time for them to do it without much to lose.

But chances are you are here because you’re on a creative pursuit.

And times have changed since the 1970s when Steve and Woz were getting started.

You have a lot more technological firepower at your fingerprints.

And most creative entrepreneurial projects can be “started” with minimal costs and low risk.

There are a million ways you can take it.

But the point is, most things you can basically start for free today.

The real hurdle is your mindset, and the time you are willing to prioritise. 

And so, regardless of where you are, I will challenge you that there is never a better time than now to start that creative business.

Life and its obligations will always be there.

It never really gets easier. As we grow and develop, we face new challenges — more work responsibility, starting a family, or health problems. 

You know the drill. 

Shit happens. 

Imagine if Steve and Woz decided it was too hard and settled for basic jobs.

Well, I wouldn’t be here now typing on my Macbook.

And you wouldn’t have your iPhone in your pocket.

Or even if you don’t like Apple, whatever smartphone you have in your pocket may not exist if Apple did not lead and pave the way.

So my point here is you can’t tell the scale of the impact of the thing you have been putting off.

And that’s a tragedy if the world misses out on what you have to offer.

Imagine what could be possible if you built up the courage to pursue that work that you love.

What if you loved your work?

I used to hate going to work.

The alarm goes off. 

Rush to get ready. 

Stuck in traffic. 

Bored out of my brain all day doing mind-numbing work.

But now it’s the opposite.

I can’t wait to work.

I want to work all the time (which has since become another problem since starting a family, but one I prefer over the opposite.)

I used to be all about work-life balance.

But you don’t care about balance when your work is an obsession.

It’s not boring. It’s exciting.

As it’s not draining. It’s energising.

It’s not a struggle. It’s flow.

You want to get up early and stay up late.

It bears repeating one of my favourite Jim Rohn quotes:

“How come you’re up so early?”

“Say, if you were headed where I’m headed, you’d be up early too. If you were gonna meet who I’m gonna meet, you’d be up early.”

It’s a totally different way of existing. 

I know “passion” gets a bad rap. It’s not the best advice for young people. Usually, they haven’t lived and worked around enough to know what their “passion” is.

They get stuck thinking it’s something they “find” or magically comes to them.

But the truth is you cultivate a passion by committing to something and pursuing mastery. 

How do I know this to be true?

I was an A student in accounting at University. But when I got on the job, I realised I didn’t like the dull, repetitive nature of the work.

I was shocked, “This is what office life is all about!?”

Hours in front of spreadsheets.

Crunching numbers.

“Please make this end.”

But here’s the funny thing.

Over time I became good at it.

And I grew to enjoy it. 

Dare I say “passionate” about it?

(I hope that doesn’t make you vomit a little inside your mouth.)

It becomes a different beast once you understand it deeply and can see all the subtleties and nuances.

Each project becomes a challenging puzzle to be solved.

A fun game.

An addictive game.

And then corporate politics and ladder climbing becomes another game to be solved.

You can see why people get hooked, right?

Only one problem:

Do you want to play this game for the rest of your working life? And sacrifice your most creative years?

If the ladder is not leaning against the right wall, every step we take just gets us to the wrong place faster.

Stephen R. Covey

There’s a wise quote.

So here’s my next challenge for you today:

Is the ladder you are metaphorically climbing leaning against the right wall?

Sure, I had made peace with accounting and found a way to enjoy it while climbing my ladder, but was it going where I wanted?

No.

How do we know?

Well, stop and consider the values you hold dear. Is it aligned?

For me, it was no.

How to find work you love

“Work you love”

Sounds a bit wishy-washy, doesn’t it?

So let’s make it actionable in 3 parts:

1. Your values

My top values for me were:

Accounting wasn’t ticking many of those boxes.

What are your values?

2. Your why

I read Simon Sinek’s Start With Why book and then took the time to craft my own personal “Why statement”.

Here’s what I landed on that was so exciting and motivating to me that I could feel it in my bones:

To inspire and support others to grow, so that we can thrive in a world of possibility.

Accounting barely touched on that, except for developing my team as a leader. 

What if I could make that Why statement my entire job? Then work wouldn’t feel like “work” to me?

This led me to coaching and writing.

Then I could directly have a positive impact on others through my words and questions. 

This led to the birth of this newsletter format — I’m trying to “inspire and support” you to “grow”.

So what could be your why statement? 

Simon Sinek recommends the format:

To ____________ [insert contribution]

So that __________ [insert impact]

3. Your strengths. 

During my odyssey, after getting laid off from work during the pandemic, I completed a Positive Psychology diploma, which was a game changer for me.

How, you wonder?

Well, since you asked:

I learned about the power of strengths through the Strengths Profile tool.

This inspired me to do another course to become accredited in the tool to assess and debrief my coaching clients’ strengths to help them find alignment in their life and unlock performance at work.

Why was this such a game-changer for me?

First, it helped me understand my strengths. Not only the ones I was using, but also those where I had potential (like writing! Maybe I wouldn’t be here writing this now if I did not discover that).

Second, it highlighted the “learned behaviours”, as they called them. These were things I became good at, but they were de-energising for me. 

Why is this so groundbreaking?

Well, I learned many of my accounting skills, which I had become good at, were learned behaviours (e.g. being organised and detail-oriented). They were getting me results but draining the hell out of me and making me miserable, as that wasn’t my natural style.

And a few of my weaknesses were crucial for high performance in accounting (time optimising, anyone?)

This was devastating for me.

I felt like a loser for being poor at organisation and time management.

Not good for a business administrator, hey?

But fantastic for creativity, flow and big-picture thinking.  

And here’s the kicker:

Leaning into our strengths makes those learned behaviours and weaknesses irrelevant. 

Most people overlook this.

Strengths give us leverage.

We have a comparative advantage when we lean into our strengths.

Want me to give you an example?

OK, I’ll tell you a little story from dinner last night.

I was chatting with a friend over the table with a glass of wine while we waited for our rogan josh and butter chicken.

He’s building a side business as a creator talent manager and sponsorship coach.

Which, as you can probably tell, is right up my alley.

Fascinating as we can chat for hours on all things creator economy.

OK, back to the main point.

He told me he cold emails 30+ people daily and loves it. Every no is one step closer to a yes.

Yuk.

Here’s the moment where I almost vomit in my mouth.

The thought of cold emailing 30 people daily and loving it seemed disgusting to me. Not my style as a quiet and non-confrontational introvert.

Yet, here he was, not only doing it, but loving it!

He was tapping into some natural strengths he had.

This sets him apart from his competition as he can go for hours, unashamedly hassling people until he gets what he wants — a yes!

I would suck at that game.

I’m not cut out for it.

Not my strengths.

But here’s where it got more interesting.

He asked what I had been up to.

I told him I had just banged out 7,000 words in a day on a newsletter series I was working on.

“What?”

“7,000 words in one day?”

This was his moment of yuk.

The idea of spending a day writing a newsletter essay for the fun of it seemed like hell on earth to him.

This was my “a-hah” moment.

Now the tables had turned.

We had uncovered a strength of mine.

I hope this story highlights the power of doubling down on your strengths — you can achieve uncommon results as you can go like the wind.

But the hard part is uncovering your strengths and learning how to use them.

And I learned that leveraging the power of my strengths made my weaknesses irrelevant.

For example, when tapping into my top strengths (like growth, optimism, and mission), my organiser and time optimiser weaknesses were no longer an issue. I had endless drive and motivation to grow and achieve my mission. 

And here’s a funny thing, my top strength was “Incubator”:

“You love to think, ponder and reflect throughout your day, every day.”

My biggest lesson here was that my thinking time was essential, not a luxury!

And here I was, beating myself up for not constantly smashing through my to-do list — no, I need time and space to perform at my best — and that allows me to create a thoughtful long-form newsletter that many others could not. 

I’ve had people reach out and say why don’t you do short-form as it appeals to a broader audience and growth is faster.

To which I respond:

No thanks, buddy, not my thing. 

I’m playing a game that feels like play to me, a game I can win. 

I don’t want to copy someone else. I want to follow a path where I become “the only”.

I tell you what, this quote from Naval Ravikant gets me jiggling with excitement:

And it should get your mind racing with possibility too.

So get out there and have some conversations as I did, but with a focus on strengths-spotting.

See what you find!

If you align your values, why, and strengths, your work will go from living drudgery to passionate love.

Wow, I went on a bit of a strengths tangent there. But it’s important, as I wanted to bring some actionable clarity to Steve Jobs’ generic advice to “find work you love”. 

Cracking this code could positively change your working life, which is maybe 1/3 of your whole life. So take it seriously.

Let’s bring it back to our hero of the day, Mr Jobs:

There are some big problems here.

First and foremost is the notion that your work is different and separate from the rest of your life.

If you are passionate about your life and your work, this can’t be so.

They will become more or less one.

This is a much better way to live one’s life.

Steve Jobs

Make sure you have something to support you before starting that business

Creative people are willing to take a leap in the air, but they need to know that the ground’s going to be there when they get back.

Steve Jobs

It’s hard to be creative and do good work when we are stressing about the bills to pay.

It’s better to test the waters while we still have a job before going “all-in”.

I took a finance contracting job for two years while building my coaching practice and experimenting with online writing. 

It takes time to figure things out, so having a support base is crucial. 

I am two years into creating and finally starting to get some traction, but it still feels like I am still on the tip of the iceberg!

Things take time, and you need to allow for that. 

Focus! Slash your product and service offering

Soon after he [Steve] returned, he slashed the company’s product offerings from seventeen to four.

This upset some fans and led to thousands of job losses, but he was unwavering in his belief that it was necessary to save the company.

“You’ve got to choose what you put your love into really carefully,” he said.

A stream of Apple breakthroughs—including iMac, OS X, iPod, iTunes, iPhone, and iPad—reflected that focused love…

The engine driving these trans­formations was a remarkably consistent set of values that Steve held dear:

Life is short; don’t waste it.
Tell the truth.
Technology should enhance human creativity.
Process matters.
Beauty matters.
Details matter.
The world we know is a human creation—and we can push it forward.

Leslie Berlin

We want to do everything.

We get pulled in many directions.

But we only have so much time and attention.

We end up doing a mediocre job.

And it confuses our customers.

That was me. I was trying to create content on five platforms without a product or service offer. What was I thinking?

What Steve did at Apple was unheard of — slashing 70% of the product line. He wanted to get back to the basics and do them really well. They doubled down on the few gems that had potential. And look where that took them.

The same can be said for you:

What do you “give a shit” about?

I loved this story from the Make Something Wonderful book. 

It’s a great test for what you really care about. 

Steve was undecided about returning to the CEO role at Apple and fighting to save the company. 

During his time away from Apple, he found success leading Pixar and built a nice family life at home (something he had previously neglected).

But he felt the calling to return to his baby, the company he co-founded. 

He called one of his mentors, Andy Grove, early one morning. Here’s Steve relaying the conversation and his thought process:

And finally, he interrupted me after about four minutes and he said, “Steve, I don’t give a shit about Apple. Why are you telling me all this?”

And I said, “Oh, OK. I’m sorry.” And I hung up the phone.

And I realized: You know, I do give a shit about Apple.

And that’s kind of what crystallized it for me. And so I went back there as an interim CEO.

Steve Jobs

Have you ever that something like that happen?

You get all wound up and passionate about a topic in conversation, but the other person couldn’t care less?

Well, this could be a clue.

A clue to what you actually care about.

What you value.

And where you should take your work.

So ponder this, what do you really “give a shit” about?

Steve on Marketing

To me, marketing is about values.

This is a very complicated world. It’s a very noisy world, and we’re not gonna get a chance to get people to remember much about us. No company is.

And so we have to be really clear on what we want them to know about us.

Steve Jobs

Your audience, customers, or clients are all busy.

Their dealing with their own messy world and don’t have time to keep up with all your details.

Following on from our last section, they probably don’t give a shit about all the things you give a shit about.

So you need to clarify the one thing you want them to remember about you.

Then consistently push that one message out into the world.

People don’t have the bandwidth to remember multiple things about you. 

That’s part of why I narrowed my brand focus to the My Creative Calling theme.

That’s one thing I want people to remember and associate with me, and it leads to everything else I do. 

It’s not about the product specs. People care about the transformation and your values 

Steve also touched on how that marketing messaging is not about your product’s specs but the values.

You don’t see Apple ads on TV banging on about how many gigabytes their products have.

No, they do things differently.

Remember the famous Think Different ad campaign by Apple?

There is no mention of computers in there at all.

No, it associates with famous innovators, artists and world changers — and speaks to those who value having the courage to think differently and change the world. 

It’s transformational. 

Your reason for being

On 29 October 2000, Steve Jobs wrote an email to himself with the subject line “Apple’s reason for being”. 

Here he detailed six paragraphs outlining that reason for being.

I challenge you to do that same, but for your work.

Send a short email to yourself outlining your “reason for being”.

Steve’s favourite quote

This quote sums up Steve in a way. 

And it challenges us to show up daily and pursue mastery of our craft.

Excellence is the product of our daily habits. 

Are your daily habits aligned with who you want to become? 

Optimism and passion are essential

It’s hard forging our own path and building a business.

It’s tempting to give up and choose an easier path.

So what did Steve think were essential traits for success here?

Well, it’s optimism and passion, because it’s really hard. 

And if you don’t really, really care about what you’re doing, you’re gonna give up if you’re a sane person—because it’s just super hard.

Steve Jobs

I remember once a friend told me I had a unique “enthusiastic optimism” quality.

But I felt like I wasn’t using it in my accounting career.

It was being beaten out of me.

But we come to life when we align our authentic qualities and strengths with our work.

And now, I am channelling that enthusiastic optimism on this creator path. And that pushes me through the hard times and struggles.

What authentic qualities have become dormant in you? How can you revamp them?

Seek out mentors

I just called them up and I said, “Look, I’m young and I’m trying to run with this company. I’m just wondering if I could buy you lunch once a quarter and pick your brain.

And everybody I ever asked said yes. It was nice.

Steve Jobs

Steve was mentored by the biggest and brightest minds in Silicon Valley.

Why?

Because he dared to ask for help.

And asking for help is a superpower.

Now bear in mind this was back in the day before the internet took over, and everyone was drowning in notifications.

Before the cold emails or pitch slaps in DMs.

Nowadays, it seems people aren’t so keen on “being your mentor”.

So you need to be more careful about how you engage if you want to build a genuine relationship.

Dan Koe wrote the guide on non-needy networking.

Demonstrate your intentions are good, you contribute value, and you show that drive and passion we already touched on. Then people are generally keen to help in some way.

You never know what may spark here.

Finally, virtual mentors are always available — like how Steve is “mentoring” me through writing this newsletter. 

Go to where the people already are

And right now, this often means social media.

That thing we love to hate.

But the reality is until we have become “known”, most people aren’t actively seeking out our work or binging our website.

No, people are busy.

And they don’t know about us.

So we need to make it easy for them to find us.

That means going where our tribe already hangs out.

This could be social media, YouTube, online groups, private communities, cohort courses, online forums or whatever else comes along.

And you need to contribute there to get noticed and capture some of that attention to bring back to your work. 

Steve did this with the flagship Apple Stores, which popped up globally on all the busy high streets.

We did things a little differently.

Our goal in retail was not just to sell to the 5 per cent of people who own our products today; it was to go for the other 95.

And we decided they would not drive ten miles to look at an Apple Store if they weren’t at all interested in buying our products.

We decided we had to ambush them. 

What that meant was that we had to go to high-traffic locations and put stores there.

Steve Jobs

Customers didn’t want to take risks in something they weren’t sure about. So by making it easy for them, it became a low risk to check out the stores.

Apple went on to become one of the world’s most successful retail stores.

Steve’s most important business lesson

The most important lesson I’ve learned in business:

That the dynamic range of people dramatically exceeds things you encounter in the rest of our normal lives—and to try to find those really great people who really love what they do.”

Steve Jobs

Work-life is much easier when you work with great people who love their work.

Steve understood this deeply. 

And be believed in the power of A-players.

He said A-players performed best on a team of A-players, and they couldn’t tolerate C-players. Steve was ruthless with this. 

This is where many disagreed with his harsh management approaches. But he believed that the quality of the products should come first.

As CEO of Apple, he spent 20% of his time recruiting.

That seems like a huge amount of time, given all that was on his plate. 

But it pays back – he believed there were no shortcuts around quality, and quality starts with great people.

This may not seem relevant now as a one-person business creator, but it still applies.

You will inevitably work with contractors or collaborate with other creators, even if you never have your own employees. 

 So seek out the great ones who genuinely love what they do.

Before you commit:

If you’re not saying “HELL YEAH!” about something, say no.

Derek Sivers

Not only will it make your life easier, but it will push your work quality to new heights. 

This leads into:

Management by values

Management by values. What that means is you find people that want the same things you want, and then just get the hell out of their way.

Steve Jobs

Steve learned this from a guy he respected at Disney.

When everyone is aligned in values, things flow.

You don’t get all that friction. 

The way I describe it is, let’s say we’re all going to take a trip together. The first thing is to figure out where we all want to go. The worst thing is if we all decide we want to go to different places. You can never manage it…

But if we all want to go to San Diego, that’s the key. Then we can argue about how to get there…

That’s what management by values is. It’s finding people with passion that want to go to San Diego—who want to go to the same place you.

Steve Jobs

This can be applied to our audience building online.

Let your values shine through in your work, and maintain your focus on that one main thing. 

Then you can build an audience aligned, one that wants to “go to the same place”.

Then it will feel more effortless. 

And on the thing you are building:

Build what you want to see in the world

You know, one of the reasons we started doing this [was] we could see that we were getting better and better at iPods, and we could see that there was an opportunity to maybe do the next thing—and what should it be?

And it wasn’t driven by a bunch of market research or financial spreadsheets about how big certain markets were.

It wasn’t driven by that at all.

It was driven by the fact that we all hated our phones.

We talked to all of our friends and all the people we knew, and they all hated their phones.

And we thought, “This is a really important device, and everybody hates it. They don’t know how to use even 10 per cent of the features that are on these phones!”

Steve Jobs

What opportunities can you see?

There must be something you wish existed in this world, but it doesn’t exist.

I know there is something you’re excited about, but maybe you haven’t had the courage to take action on it.

For me, it was this newsletter.

I needed inspiration and support in starting my creative journey (back to that Why statement). So I started building it to help me, knowing it would help others grow.

My final challenge for you today:

Start building it.

Reflection

I’ll keep this one reflection short as it’s a long letter, and there are already a bunch of reflective questions littered throughout each section.

So on that wonderful thing, you would like to see in the world:

What is the smallest possible action you could take today?

Keep asking yourself that question each day.

And keep acting.

You will be amazed at where you are a year from now. 

A quote to ponder

Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. 

They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. 

About the only thing you can’t do is ignore them. 

Because they change things. 

They push the human race forward. 

And while some may see them as the crazy ones, we see genius. 

Because the people who are crazy enough to think they can change the world are the ones who do.

Apple’s Think Different advertising campaign

What happened this week 

I’ve invested in some courses to improve my writing and newsletter process.

Let’s see how I improve over the coming weeks/months. 

Final thoughts 

Today’s writing background music was from one of Steve Jobs’ favourite artists, Bob Dylan, with the album Highway 61 Revisited. 

Lol, it feels like I am becoming a bit of a method actor for these writing pieces and getting into the character’s mind. 

If you enjoyed this newsletter, please share it with a friend, and if you haven’t already, sign up here.

It would be great to have you on board!

Cheers!

Matt K. Head

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