Mar 18, 2013 · 4 minutes

You sell your company, make millions of dollars, and now you get to choose how you want to live the rest of your life. It probably makes sense to splurge a little bit.

A fancy watch, new car, and bigger home are some of the obvious ones that jump to mind. These are the creature comforts that people want and deserve to have, once they have the means to attain them.

Unless, of course, your name is Graham Hill and you live an ascetic, minimalistic, stripped-down, environmentally-friendly, quaint, simple lifestyle. For those of you who are actually ascetics and actually live in caves, you should probably know that Graham Hill is the founder of TreeHugger, an environmental blog that sold for millions to Discovery Communications.

Now he lives an ascetic, minimalistic, stripped-down, environmentally-friendly, quaint, simple life... and achieves all this by giving TED Talks, appearing in the New York Times, and proudly presenting his home on Vimeo to visitors of his site. Just like a hermit.

He’s also handsome, charming, and loves taking close-up photos of his divinely-crafted face. Just like a Buddhist monk.

Far be it from me to tell a handsome young millionaire how to live his life, but I’m not sure Hill’s faux-asceticism is really an embrace of discomfort. He seems to be very comfortable on stage talking to people at TED or dancing around the pages of the NYT, Business Insider, etc.

Has he even left his comfort zone at all?

I’m not going to tell Graham or any successful person what to do after they make their riches. I’m not going to tell a person who hasn’t made their riches what to do with their lives. But I think people as successful as Graham Hill got that way not because they embraced material or physical discomfort...

It’s because they embraced career discomfort.

They quit perfectly secure jobs where they were likely to get promotions in the next few years. They moved from towns where their friends and family lived in order to be in San Francisco or New York. They took their life savings — $80,000 or so — and spent half of it in six months on a contract PHP developer, who got them a prototype around which they could fundraise.

They told their girlfriend that they wouldn’t see them as much. They started asking their parents to help them with things that a 30-year old shouldn’t have to ask their parents to do anymore. They sent their future children to future public school. They risked getting laughed at by everyone they know.

But through it all, they probably still had their 2009 Acura or the Tag Heuer watch that they got for graduation. And they probably still have cable and HBO and a Netflix subscription. Yes, they still go to restaurants, but less often. They may even own a fancy Italian suit.

As I look forward to my next venture, I am making very few material sacrifices. I have no problem upgrading homes, watches, or any other material comfort that I couldn’t afford several years ago. I like nice things.

I am not, and I will never be like Graham Hill. But my life is about to get very uncomfortable. Starting a company from scratch involves doing things that you hate having to do, no matter how nice a car you drive.

My seed round does not afford me the luxury of an HR manager or recruiters, so I am going into LinkedIn and begging people I don’t know to accept my phone calls. A lot of them, and it takes hours each day to send out those “Join My Network / Please Take My Call” invitations.

My previous success will not change the fact that I am working insane hours and am now eating ‘stress food’ again, even though the one thing I was supposed to do this year was get into shape.

Nothing I did in the past will enable me to be in two places at the same time — half of my initial employees will be outside of California — so I’m going to be in a long-distance relationship with my girlfriend half the year as I work out of Brooklyn.

Raising a Series A is like getting a rectal exam and having the doctor accidentally lose the results four times per week for months on end. It is horrible for first, second, and third time entrepreneurs alike. It will be the story of my Summer 2013. My previous venture may help my odds, but it sure as hell won’t make the process any more comfortable.

Waking up early when shit goes wrong — site outage, editorial emergency, New Yorker forgetting what time zones are — will be part of the gig. Life is about to be very uncomfortable for me, made all the less comfortable by the knowledge that I don’t have to do this to myself.

But that’s the kind of life that I am choosing to live, because that’s what makes me happy, taking a comfortable career situation, and making it an uncomfortable career situation.

And that’s the kind of person I look for when I’m starting my new business. I want to hire people who are very comfortable right now with their jobs in engineering, editorial, and sales — and I want them to get as uncomfortable as possible.

Together, my team and I will be an often-miserable lot. I do not relish spending the next five years defusing go-nowhere arguments between engineers, editors, and salesmen.

My new Armani suit will not shield me from that.