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How to Make A Real Living Doing What You Love

Eight years ago I quit my day job and started doing what I love as a career. You’ve probably heard this story a hundred times from entrepreneurs and self-help gurus. In the story, making a living from what you love is as simple as making a mental shift and perhaps signing up for an online […]

Eight years ago I quit my day job and started doing what I love as a career.

You’ve probably heard this story a hundred times from entrepreneurs and self-help gurus. In the story, making a living from what you love is as simple as making a mental shift and perhaps signing up for an online course sold by the person telling the story.

While inspiring (and self-serving), that’s not how it actually happens. It takes a lot more. Your skepticism is warranted.

The good news is that it is possible, though. You really can quit your job and make a living doing what you love. I’m living proof; I make my living helping people have truly meaningful relationships with more love than they thought possible, and this is something I would do for free if I didn’t get paid for it. I’m living the dream as a relationship coach who actually makes good money doing what he loves.

What people don’t normally tell you is that living this dream takes far more time, effort and planning than the narratives usually lets on. It isn’t easy. But it is possible.

So here’s how you can join me without the need for luck or any particular superpower. But sorry, no quick fix to follow. Also no online courses to sell you.

1. Fill a Need, Not Your Ideal

The first thing you need to know is that the difference between idealistic and an ideal life is selling something that other people actually want to buy. I can’t tell you how many times I see this mistake play out, and how it separates those who try and fail from those who succeed at making a living from what they love.

You probably love doing many things. Not all of those things will earn you a living, though. Or they might earn you a living, but not in the way you imagine. So when you embark on this dream job, start by figuring out something people actually want and will pay for. What market need are you filling, and are you sure you’re filling their need and not your own fanciful desire to do something specific and get paid for it?

When I started my relationship coaching practice, I wanted to help people cultivate unconditional love. But as I quickly found out, nobody really wanted that. I couldn’t make a living with that. What people did want, specifically singles, was a lasting relationship. So I started focusing on helping people get married instead. That is when I started earning money from my passion. I found a part of my passion that filled an actual need in the market.

2. Keep it Small—Or Hire it Out

The second thing you need to know is that not everyone should be Steve Jobs or Elon Musk. Making a living doing what you love doesn’t mean your business must grow big and international. You don’t necessarily need employees or wild seven-figure success.

Is your goal fame or doing what you love? For the latter, all you need is enough to live and support a family. And by keeping things small, you’re much more likely to spend your time doing what you love instead of morphing into a captain of industry. So think small.

Not that there’s anything wrong with dreaming big, of course. My roadmap includes a large relationship practice with a global network of associate coaches and allied professionals, as well as an online school and a MyFitnessPal for relationship health.

But if you plan to go big, hire out everything that isn’t your core passion. Automate or outsource everything that’s not a true passion so you stay focused on what you love and don’t run yourself ragged.

An early mistake I made was building my own web site and handling my own appointment scheduling. I should have used a service like Amidship, which gives service businesses like coaches and personal trainers an easy way to set up a web site, automate appointment scheduling and handle invoicing. I probably would have been making a living from coaching at least a year sooner if I had used Amidship instead of doing everything myself.

Use such services widely, and hire your way out of tasks you don’t love (like writing this article; notice I have a coauthor on this piece).

3. Be Ready for Bad Days

One of the most important keys for making your living from what you love is realizing that there will be many hard days before you turn the corner to profitability.

What saved my dream business was the early decision that I would persevere no matter what problems confronted me along the way. I took as fact two hard truths: There would be many hard days, and I didn’t know how hard it would get. All I knew was that I would persevere and succeed in the end. I wouldn’t give up no matter what happened along the way.

Honestly, this saved my business more than once—and it can save your dream business, too. When you expect the hardest journey of your life, and you expect the headaches and the setbacks, the startup problems you do face are not as insurmountable. You knew they were coming. You built setbacks and failures, long hours and nightmare problems into the model. So when they hit you, there’s no question of giving up because you knew this was part of the process.

My first relationship client was an utter disaster, and one year I worked until 5am on Christmas morning. I’ve had equipment break while shooting on location, business partners who failed at the critical hour, and big assumptions that were wrong. But I never even thought of giving up because I knew this was the process. The result is that I’m still doing what I love professionally while many of my relationship coaching colleagues gave up long ago.

4. Iterate Along the Way

There’s a path to making a living from what you love, but the truth is that you don’t know the path yet. Almost nobody does. I certainly didn’t.

The idea for a product or service that allows you to follow your passion won’t be the product or service that actually makes you money. You will need to iterate and evolve your ideas as you go along, especially if your goal is doing what you love. What sounded like a good idea might not work in practice. What looked like a sustainable business model could turn out to be all wrong.

This is a blessing in disguise, though.

If you know your journey is filled with evolution and lots of unknowns, you don’t get bogged down in the planning phase. Things don’t have to be perfect because you know you probably will get it wrong the first time, so the burden shifts from having it all correct at the start to pushing out minimal viable products and seeing what sticks. This is very freeing.

But it does take patience and a willingness to try things along the way.

At first I envisioned a coaching model where there was weekly client homework and a long exploratory phase at the beginning, for instance. But this was me teaching instead of coaching, and almost none of my clients liked it. So now we do nothing like that.

I also thought that content marketing would be my primary way to attract clients, but webinars and word of mouth proved far more effective. So I still produce a lot of content, but I focus much more on important interpersonal relationships for my business now.

5. Block Off Time for Your Sanity

It sounds strange, but the fifth key for making a living from what you love is not letting the business take over your life.

As personal development authors Preston Smiles and Alexi Panos note in their book, Now or Never: Your Epic Life in Five Steps, you need balance when running a business based on something you love.

There’s always more you could be doing for your business as an entrepreneur, and the pull is twice as strong when this business is based on something you love. The problem is that this creates burnout, and somewhere along the line doing what you love becomes serving something you formerly loved. You can wreck your passion if you don’t keep balance.

The key is blocking off time for activities outside of work, even if you enjoy what you do. Schedule time for the kids. Make room for reading and personal development. Defend social time with friends.

Remember, you’re working on your dream job. This dream probably doesn’t include spending all day, every day on work. You need a balanced life so your dream job stays dreamy. Otherwise you burn out.

I fell into this trap myself the first few years of my business. I was almost the relationship coach without any relationships because every waking hour was spent on my business. Thankfully, I eventually woke up and reasserted the balance. My life got much more sustainable when I did, and so did my happiness.

So I gave up my day job and now make a living doing what I really love. You can, too.

It might not be quick or easy, and there will be false starts along the way. But it is worth it; that part of the story people get right. Making a living from what you love is pretty special.

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