In a world of people who are out to climb a ladder, make a name for themselves and feed their ego, truly humble, authentic and generous people stand out.

Tim Hoiland is one of those people for me. Tim is a writer and the founder of Hoiland Media. I met Tim several years ago when we were both involved with a project for Christianity Today. His thoughtfulness and ability to empathetically listen struck a chord with me. I was privileged to write a few pieces for a site he ran called FlourishPhoenix.com. We recently reconnected and without any notice, I asked Tim if I could record a conversation with him for my blog. He obliged and we had a really interesting chat.

SS: Tim, tell us about yourself and what Hoiland Media is about. 

TH: I started Hoiland Media a little over 2 years ago. I work with a handful of clients – I’m basically a one-man communications department for some startups, non-profits and public figures. They don’t have a full blown media or communications department, but they benefit from my skills. We tailor my work to their goals. Sometimes, that’s writing blog content, web copy, email campaigns, or even strategy.

SS: Why are you passionate about communications and marketing?

TH: Growing up, I wasn’t always an A student. I really struggled in math and science. I discovered in junior high and high school that I was really into the social sciences; they were a lot more interesting. My freshmen year of college – in a Gen Ed English class – a professor encouraged me to focus on writing because he saw a strength there. He wasn’t the first person to affirm that, but it had kind of snowballed. By my senior year, I just stacked my schedule with all writing-intensive classes. At my school, they added a W to classes which required a lot of writing and I just chose all of those. A lot of people hated those classes. I could write essays all day long; just don’t give me a multiple choice test about the periodic table.

I think it was something I discovered I was good at. I have a bunch of other interests, but writing has been a hard skill. Sometimes, you have to take a career step following hard skills rather than a heart passion. And maybe eventually you can pull those two together. I’ve found some of that over the years.

Tim Hoiland on Connecting Your Work and Passion

SS: You talked about your hard skills and your heart skills lining up eventually. How have you worked that out? Because I think a lot of people who have the job that pays the bills, but it doesn’t make them excited. At some point, they say, “I’m frustrated with this dichotomy and I really want to integrate these two.” How do you bring them together? 

TH: I’ve had different seasons where the work I was doing wasn’t life-giving, so I found ways to supplement. I would say it’s a bit of a luxury we in the West have to even ask that question. Throughout history and for many people around the world, that question is a luxury because they didn’t or don’t have a lot of options. It’s a matter of survival. There’s a lot we can learn from people who came before us and around the world about work, fulfillment, and vocational calling. If you’re born on a farm, you’re don’t have a lot of options – you’re gonna be a farmer. A good farmer!

But I am aware we do have those options. People with college educations really can choose what they want and what they spend their time doing. Starting out, you have to prepare to do things you love and not necessarily get paid for them while you get better. Once you develop trust and a reputation for quality work, you can start being pickier. I’m self-employed, so I can pick and choose who and what I want to work on. Sometimes, that means picking something which earns less money because I really believe in it or enjoy working with that person or team.

Right now, there’s a mix for me. I believe in all I do, great clients and organizations. There’s a some which don’t make a ton of sense from the earning standpoint. So, having multiple end goals with your work matters.

SS: In the creative world and in the world of entrepreneurship  fear is a very real battle. How have you battled fear? 

TH: Specifically as a writer, there are at least two different kinds of fear. The first one is internal, “Am I actually good enough?” You hear about writers block. You hear the voice which says, “Am I consistently going to be able to crank out all this content?” In my world, that’s writing stuff for clients. I have to stay mentally sharp. I can’t sit around just thinking about what to say.

The second one is very different – “what are you going to say?” and “what’s the external ramifications of it?” I write pretty uncontroversial stuff  for clients – I believe in it and it’s good stuff but it’s pretty safe. In grad school, I studied International Development. I did research around a community where there was a contentious foreign mining company. I went and interviewed people where other people had been abducted or killed for opposing this. That was a different kind of fear.

So my internal fear feels a lot smaller than writers in places where there are totalitarian governments or Christians who are risking imprisonment or worse for what they’re saying. In the big scheme of things, it doesn’t feel like a lot fear.

Tim Hoiland on Staying Fueled Creatively

SS: You talked about the load of work you carry. You have to generate a significant amount of content for your clients. What do you do for yourself to stay engaged and refueled so you can do that? I know a lot of people who work in a demanding environment feel sucked dry and struggle to stay fueled. 

TH: For me, having acquired the hard-writing skills, the biggest challenge is to read the stuff I enjoy reading. I’m continuing to improve my skills constantly as a writer, but reading is the key. Not just reading for the assignment or something I’m researching, but just stuff that I want to read. That can feel selfish or frivolous, when I go read a 600 page biography on Steve Jobs. When you read good writing consistently, you can’t help but absorb that. The way I’m wired, when I read good writing and stuff that’s interesting, it stimulates my mind and heart. I sit back down and write from my heart, while not feel like I’m stuck in a rut or an echo chamber. Whether it’s reading the New Yorker (which always impeccable writing) or theology or a biography or a book about baseball, it helps. Reading good stuff helps me write good stuff.

Tim Hoiland on The Unglamorous Entrepreneur

SS: Last question. Someone is reading this – they’re resonate with your story. They’re a writer, in communications, a business owner or thinking about starting something. They feel stretched, afraid of risk, outside of their comfort zone, maybe even insecure. What would say to them about their battle with fear?

TH: From my experience, it was a scary thing to go off on my own without job security, health insurance or retirement. There’s always risk involved when you go off and start your own thing. It’s always a risk – it should be a calculated risk. And different people are comfortable with different levels of risk. I had a pretty good hunch that it could work. This hunch came from the work I had done, the network I had built and the sense I had of a demand for the work I wanted to do. I had met enough people that I felt like I could build something with this. I made an educated risk – I counted the cost.

But I would also say be really open to learn from other people, to adapt. You want to project confidence but you also want to project teachability. If you’re going to launch out, you need the posture of a lifelong learner. What you may initially intend to start may not be what you’re doing 6 months from now. Some people are stuck in jobs they would rather not be stuck in for fear of risk and maybe they do need to flex their courage muscles and step out.

But there is also a glamorization of entrepreneurs right now. Not every one at every season or time should be one. It’s been awesome doing this, but it’s not glamourous. People think, “If I do my own thing, I’ll be able to set my own schedule, charge what I want to charge, make what I want to make, take time off when I want. Live this dream life and people will look up to me because I’m doing something awesome.” That illusion is going to come crashing down pretty fast. Anyone who has built something will tell you that. So, have reasonable expectations. If you feel like there’s enough of a chance of success, take the plunge….and pray!

Thanks Tim, you were super gracious! If you want to follow Tim’s writing, check out his blog. If you want to talk to him about partnering with Hoiland Media, click here. And if you want to follow his tweets about good books, baseball and great food, follow him on Twitter.