Inspiration when single – an entrepreneur’s guide
Posted by shannonclark on February 15, 2008
As I write this it is Valentines Day, restaurants are full, hearts are everywhere, and couples are kissing and holding hands. On twitter a cool graphical hearts feature has been getting a lot of use (at least amongst my friends). Friends who are parents report that their children are excited about giving cards to all of their friends.
But this post is not just about Valentines Day and how I am single today as I have been for by far the majority of past Valentines Days (I’ve only had a date on Valentines Day 4 times in my life – and I’m 33 so do the math, fairly pathetic).
No, this post is about how and where to find inspiration when you are single and an entrepreneur. Something I have been thinking a great deal about (and struggling with) for the past few months.
I do not like being single. I know there are some people who do, some people who enjoy the “freedom” or for whom being “single” means lots of dating, lots of somewhat meaningless relationships.
But that is not me. And though I respect my poly friends, I am probably not poly (heck just being in one relationship is such a rare occurrence in my life the concept of having multiple relationships at the same time is well nigh unthinkable).
The world, however, is structurally set up for people to be in relationships – to be couples, not to be single, especially not as middle aged adults (I’m not actually comfortable calling myself that but at 33 going on 34 I’m no longer “young”). Prizes every where are for tickets for 2, homes and lifestyles and deals and expectations everywhere are that past some period of early adulthood most people will settle down into couples (and then in most cases into families).
I overheard a group of people at a restaurant a few weeks ago talking about dating, with one of the guys at the table talking about how hard it has been for him to have gone 30 days without sex. Don’t get me started on that (let’s just leave it at I broke up with my last girlfriend in the spring of 2006 – I’d be thrilled if it was “just” 30 days..) . But from the conversations at this table (mostly guys but one woman) the expectations there were that they all would and could date and date frequently and that “dating” led to sex on a regular and frequent basis – whether with the same person or multiple partners.
What does all of this rather personal stuff have to do with business?
Or with being an entrepreneur?
Well there is a key question for everyone to answer – what (and who) are you working for?
What do you want from your career? Why do you want (and need) money? Fame? “Success”? In short what is success for you? And how does that drive you? More crucially how will you know when you get there?
And then, if answering all that your path is to be an entrepreneur, how (and can) you get there?
If you are not single you have some fairly simple answers to the above questions – many people would answer that they work to provide for their partner & for their children (or future children). As they work, a partner is someone whom you can lean upon, someone who comforts you when you are down, someone who helps balance out your life – and on a very simple and practical aspect, someone who can take some of the load of life off you when necessary.
Now I don’t just mean couples who have a traditional (though not so much these days) life of one partner working, one “keeping the home/raising the children” even with both partners working one can usually take some of the chores of life from the other – cleaning the dishes, arranging for dinner, picking up the dry cleaning, paying the family’s bills, waiting for a delivery, etc.
But if you are single what do you work for? Who (or what) can you rely upon for support?
Where, in short (okay in long form), can the single entrepreneur draw inspiration?
I’ve been asking this of myself for the past few months. The life of an entrepreneur can be mentally challenging, you rarely if ever can be “off” – I only slightly jokingly describe it as “you always have something to do when awake, and when you are sleeping you dream about it” but that’s not all that far from the truth. Yet, besides “work” you also have a life – all the small, little things of living which collectively add up, which all take time and to a degree attention.
Here in Silicon Valley many entrepreneurs (and others) are fans of “Getting Things Done”. A part of that system is to create contexts, to think both about your very long term goals and your tasks for the next hour. And yes, from a tactical standpoint GTD can be very helpful and from the perspective of a process, of a way to think through what you are working on, what your goals and requirements are it is very helpful.
But from a deeper, personal level it only helps with the tactics, you still need to find what your personal source of inspiration is, to have an answer for yourself what you are working for, and to find some alternative (or alternatives) to the help that someone in a relationship gets from having a partner (or as I noted, partners).
For me I have historically had great friends and a great relationship with my family, both my friends and my family have offered me an emotional outlet – someone to talk to about what my goals are, to vent my frustrations, to relax with when that’s what I need. But two years ago I moved from my long time hometown of Chicago to San Francisco. At the time I was in a relationship (she followed me a month later) but a few months later she and I broke up and she moved again (to Mexico). We’re still friends, but now I’m in a new city, far from my immediate family, and though I have many friends here I don’t have the same type of friends as I had back in Chicago (i.e. friends whom I had helped move, whom I had known for years, had helped through crises and in turn had gotten help from).
So for the past year or so I have been seeking answers – been looking to myself for why I am an entrepreneur, what I am looking to do both in the short term and in the longer term. In part I also have been looking at myself. I still hope not to end this year single – I do think being a relationship is a better state for me than being single – but I also have to find answers that work for me if I’m still single.
This is a post without easy, simple answers but here are a few which at times help me, not to say I always keep my own advice, so in large part this is also to be a reminder for me as to what I should be doing, what I can change over the next few months which might, just might, help.
- The life of an entrepreneur can highly varied, build into your week some regularity. Lately every Wednesday morning I have been having breakfast at 9am at Chow on Market St. (and inviting anyone to join me).
- Don’t let your personal space go neglected – if this means dropping off your laundry and paying someone to do it vs. doing it yourself do that. A cleaner could be a great investment – but even just always (and see point 1 schedule this) spending an hour or less cleaning and imposing order on your living space helps considerably.
- Don’t let you go neglected. Get exercise, eat healthy, schedule regular doctor and dentist appointments (all of which can be very hard when being an entrepreneur, especially the last two before your new company has group medical plans, one of the early things you should do for yourself and your first few hires).
- Even if you can work entirely from home, don’t. Sure, work from home some of the time, but even more so as someone single, getting out of the house and having face-to-face human interactions is really, really important. It is all to easy to order in, to keep really odd hours, and blink and realize a week has passed and you have barely seen another human in person. This is not healthy.
- Every few months do a brutal clearing out of junk from your life. Donate all the free t-shirts & schwag you have collected (so you aren’t tempted to just get by wearing poorly fitting free logoed t-shirts). Clear out of your kitchen expired foods – but also unhealthy temptations. Recycle pile of newspapers and magazines. Online this means hitting a reset on your RSS feeds, it also means unsubscribing from mailing lists you haven’t read in months and stopping emails from vendors & analysts you never read or reference. In 2006 I moved so many times this happened naturally, in 2007 far too much clutter & junk accumulated in my life both online and in my home.
- Find a small set of peers and find a way to gather, in person, and talk openly and deeply with them on a regular basis. This can (and should) be hard, but seek this last point out. By peers I really do mean that, find people who are or have been doing something similar to what you are doing – other founders (perhaps though in other industries) and find a way to gather in a small group on a regular basis and talk. This might be over a dinner or even a card game – and the point here is NOT to do business together (if anything that might hurt the goal) rather the goal is to have a group of people who can tell you that you are being stupid, who can give you tough truths. Someone in a relationship hopefully has that type of honest from a partner – but especially as a single entrepreneur it can be very hard to be told the harsh but helpful truths. And it can be hard to find a way to speak out loud about ideas you are considering. I haven’t yet found this precisely, but periodically over the past year I have, at times, had some really amazing conversations in small groups which scratched the surface of this issue – conversations with friends who told me tough truths – who challenged and even yes confronted me. This can, should, be hard. But I’m serious, seek this last bit out.
- Don’t go overboard but build into your week some personal pleasures. No, I don’t mean reading even more blogs on your industry – no matter how passionate you are about it. What I mean here is you should keep up with some of the things which are why you live – are what you take a great deal of pleasure and enjoyment from. For me this is great food and good writing (especially science fiction). To a lesser extent it is also staying current on US politics and a bit of everything else by reading the New Yorker every week. On Saturdays I try to get to the local Farmer’s Market (both so I have healthy snacks and food to start the week and for at least one great meal that week). And even on weeks when I can’t finish a book I try to listen to two of my favorite podcasts – one a one hour discussion of music (Sound Opinions) and the other a weekly podcast of great short science fiction & occasional fantasy stories (Escape Pod).
However even sticking to all of the above won’t help if you don’t find an answer for yourself as to why you are an entrepreneur – i.e. what you are trying to do. This is tough – but seek out an honest answer for yourself and set those goals. At some point in time being very aware of your own goals and reasons will help you make a tough decision – when to stop, what to sell for, when you have “won” etc.
If you are in a relationship I think you should be honest with your partner and discuss your goal for your venture – but being single it can be harder to share your goal(s). Share it publicly and you might divulge something which could hurt you in the future (i.e. when someone is potentially investing in your company or considering buying it). But even without sharing all the details and specifics at least as an exercise for yourself write these goals down – even if only on paper and in the privacy of your own home.
Revisit these goals on a regular (at least once a year but I’d suggest more like once a month) basis and see how you are making progress towards them.
Keep in mind why you are doing what you are doing and, in fact, you have a greater shot at achieving it.
For me, again without naming numbers, here are after much thought what I want – why I’m trying to start something big.
- I want a lot of freedom and flexibility – for me this does take some real resources. I want to be able to say no to a lot of people – I want to make my own choices.
- In many respects where I want to live are not cheap places – nor, in fact, is it a singular place – I want to live and put down roots in more than one city (indeed perhaps in more than one country).
- Eventually I do want to be a father – I feel I could be a good one – and thus at some point I want to be able to give my children the opportunity to pursue (and excel at) their dreams.
- I want to build many things which will outlast me – and in doing so I want to help a great deal of others (individuals and companies).
- I want to see my ideas tested – that is I have (and I suspect always will) have many ideas, I’m an entrepreneur in part because I want to take those ideas and see them turn into reality into actual products and services which help others and impact the world. I then want to keep repeating this – and to help many others do the same (take great ideas and make them real). At some point I suspect this means I’ll be either an angel or VC investor myself – but to get there I probably have to see a few of my ideas through to success first.
- And I want to teach. I’m not sure where, but my fantasy of “retirement” has always been to get a PhD (or not to need one) and to teach – but to do so on my own terms and without needing to play political games (“publish or perish” etc). I think I can be a great teacher – but I also want to do more than just teach – I also want to do.
What are your inspirations?