Does the tranquil business owner really exist?

March 19, 2010 1:10 PM

Do business owners and freelancers ever learn to relax while running their own businesses? And if so, how do they get to that point?

My admittedly anecdotal and limited experiences working for people who run their own companies suggests to me that most business owners are workaholics, obsessing over their business 24/7, 365. I'm really interested in entrepreneurship and understand a lot of the benefits of starting your own business, the potential freedom and intellectual stimulation that can come with being your own boss. I also understand the beginning is almost always incredibly demanding, and that most small businesses fail because it is so difficult.

My question really has to do with the "successful" businesses that have made it past the 5 year mark. Do these owners ever get to a point where they can leave on Friday evening and not think about work until Monday again, or is obsessive business thoughts part of the trade off until you retire or sell your company?

posted by the foreground to Work & Money (17 answers total)

My dad was a successful architect with his own small firm, and he never relaxed. He worked just about every day my entire life, dying a week before his retirement party at age 62. That has made a huge (negative) impact on my work ethic and desire to own my own business.
posted by MrMoonPie at 1:23 PM on March 19, 2010

You may want to read The 4-hr Workweek. It wasn't my favorite book, but getting to the tranquil owner stage is exactly what the book is about and it covers how to do it in great detail. Worth a read if you're interested in how it can be done.
posted by widdershins at 1:25 PM on March 19, 2010

I've worked at a number of independently-owned businesses in Manhattan, mostly boutiques, so I may be a bit biased re: appropriate amounts of stress and hustle. The owners were always the restless type, the kind to whom tranquility was not something desired and who were given an endorphin kick when the coal was being shoveled into the engine as fast as humanely possible. One of my bosses would sleep in the store basement (there was a couch.) Another would go out on the town with her boyfriend only to drop by at midnight to make phonecalls to her manufacturer in India and check what the register was at. I once got a call to check the register from my boss vacationing over at Burning Man for chrissakes.

I guess what you see as a "trade-off," these people saw as their vocation. Yes, they were stressed and yelling, but it was pretty clear that this mishegoss was what they wanted out of life.
posted by griphus at 1:34 PM on March 19, 2010

Another anecdatapoint: my dad has a private bankruptcy practice and is pretty chill about it. I'd say he works about 9-10 hours a day and doesn't usually take lunch, but has absolute freedom over his hours and stuff. He came to every one of my sports games in high school, which was pretty cool.

I think it depends a lot on the business and how long you've been doing it. He's been at it for almost 30 years and has developed a strong brand in our hometown. I don't know, but do suspect, that it was probably a little scarier and more intense when he was just starting out.

He also doesn't see himself retiring, but does plan on winding down the practice and starting to only take easy, softball-type cases in another 5 years, I think.
posted by Aizkolari at 1:34 PM on March 19, 2010

In my experience it looks like the answer is no, but its worth considering that a lot of these type of people probably wouldn't be able to relax if they had a job either.
posted by jeb at 1:35 PM on March 19, 2010

Best answer: From a few observations: some causes of being able to have a relax while running a business:

1. Alcohol.
2. Pre-existing wealth as a cushion.
3. Naivety.
posted by rongorongo at 1:37 PM on March 19, 2010 [3 favorites]

I've been doing freelance webdev stuff for the past 10 years. I am all too capable of relaxing but then I may not be a prime sample as I am happy to live a fairly minimalist life instead of being a workaholic to make more money.

also, alcohol. and my husband has a pretty good job (ie I dont have to worry about health insurance, which would probably be the biggest source of stress and expense for me if I were single...) YMMV I suppose.
posted by supermedusa at 1:43 PM on March 19, 2010

I've run my own consulting business for 15 years. I guess the fact that I'm still at it full time makes me 'successful,' but I have never felt successful. I travel 4-5 days per week (spend an average of 140 nights a year in hotel rooms). Weekends are pretty much socked in with work, either catch-up or planning. The work is okay, but it's just that: work. There are occasional satisfactions. The income is good, the independence is good, a few of the client people are a pleasure, and the best part is no two weeks are alike. But can I / do I relax? Not much.
posted by charris5005 at 1:43 PM on March 19, 2010

Best answer: I've worked for small companies for most of my employed life. In 99% of the cases the owner obssessed over business all day, every day. At a few of the smaller companies, the owner would call me at home (I was a combination salesperson/administrative assistant. Probably one of the reasons the four-person company was able to rack up $5 million plus in sales every year was because the owner was adverse to hiring extra help and all of us wore a variety of hats.) on Sunday night with a barrage of questions he'd come up with since quitting time Friday (Have you aged the receivables lately? Is such and such shipment going to be ready?) and wanted me to be ready to provide answers first thing Monday AM. The owner at another of these companies came in to the office no matter how ill he might be (and insisted the same of his employees, unfortunately) and only ever took one week of vacation, and always the week between Christmas and New Year's, since most of our customers were closed during that time. Mind you, all of these owners were successful, had nice homes in wealthy suburbs (Boss That Called Me on Sundays paid cash for the full amount of his $350,000 house in 1987), but I always got the impression that whatever they had was never "enough" and that they feared it could all disappear overnight.
posted by Oriole Adams at 2:11 PM on March 19, 2010

I'm freelance and have been since 2003. I think at some point I just realised I made enough every month and it was cool. I find deadlines (of which I have a lot) stressful occasionally. Other than that, not really. Sometimes I work really hard and sometimes I do comparatively little. I hardly ever work weekends. So I guess I've learned to relax. But I don't think I've ever really fretted about work, so maybe I've always been that way.
posted by rhymer at 2:15 PM on March 19, 2010

I'm freelance and have been since 2007. I find the stress of being self-employed pales compared with the stress of going to a job I hate. But I have been very fortunate in terms of new business and cashflow. Also, I'm a sole practitioner. If I had employees, I bet I'd be sweating it a lot more.
posted by ottereroticist at 2:47 PM on March 19, 2010

Best answer: I think there is a set of entrepreneurs/business owners who manage to compartmentalize their lives to some degree, setting aside time regularly for relaxation, family and personal development. From what I've seen, they share a few common characteristics:

• Effective delegators, with able staff
• Have strong personal interests, outside the for-profit sphere
• Have strong spousal and/or family attachments
• Have good networks of long term friends, who knew them before major business success
• Like to travel
• Value novelty in personal experience
• Aren't afraid of damage to their public images, from being seen outside normal social and business roles

Well known uber-examples: Sir Richard Branson, Warren Buffett, and Jack Welch. But in making this list of attributes, I really think of probably 2 or 3 dozen 7 and 8 figure net worth people I know, who have a limited, local public visibility, mostly as successful business owners in their hometown communities, and yet really have crafted great, interesting, well balanced lives, one part of which is their businesses.

I was talking with one of these people today, a woman who runs a number of beauty supply businesses in the Southeast US, and she told me that she is taking all 7 of her grandchildren (ages 9 to 17) to the Dominican Republic in June, where they'll all spend a month working in support of Haitian earthquake relief. She has a nice vacation home on the north shore of the DR, but they're apparently eschewing that for more primitive digs in San Juan de la Maguana. I asked her how she was able to just pickup and leave her businesses for a month, and she said "I always thought it was worth whatever it might cost, to go away occasionally, if only to learn or confirm who in my company I could really count on, in a pinch. But this trip, it seems I'm carrying so many good wishes and the moral support of my staff to people in need, that they'll (meaning her staff) probably make me look bad, in terms of earnings and performance, while I'm gone!"

That's a real ability to delegate...
posted by paulsc at 2:48 PM on March 19, 2010 [4 favorites]

I've had my own consulting practice for 16 years. When I'm really busy with work, I may work some long hours and even some weekend hours very occasionally. The weekend hours happen maybe once a year at most. When I'm not very busy, I've certainly learned how to entertain myself until more business comes in.

Some years have been very good, businesswise. Some years haven't. I take it in stride. Although the economy largely forced this on me, I find I kind of like describing myself as being semi-retired now.

But not only am I my own boss, I'm not anyone else's boss either. So I don't have anyone to look out for but me. And my husband and I live pretty frugally (which, I believe, is an absolutely essential ability in anyone who is contemplating self-employment), so it's no sweat if business is down.

Also, I work out of a home office so I always have access to my computer and the like if some idea occurs to me during off-hours.
posted by DrGail at 3:16 PM on March 19, 2010

Best answer: Forgot to add to my list that the businesses of people who "tranquilly manage" also seem to me to share some key characteristics:

• Mature internal financial systems, with appropriate audit controls and reporting
• Clear business succession plans, of which all key employees are aware (nobody near the top should be wondering where they'll be left, if the boss croaks or sells out)
• Good advisors or boards
• Low debt to equity ratios
• Equity or profit-sharing plans that reward performance in line personnel, and capability in staff positions
• Terrific customer loyalty and retention, usually due to extreme levels of customer service and attention
• Clear operations procedures and documentation
• Ongoing emphasis in employee training and development
• Friendly, fair but firm administrative culture. Opinions and alternative views are welcomed, but decisions and policies belong to management, and are worth following, because of shared desires for individual and overall business success.

posted by paulsc at 3:19 PM on March 19, 2010 [5 favorites]

Best answer: I recently bought a retail store and have owned it since November. For a business owner, I live a pretty damn tranquil life, but there are a few reasons this may be the case.

One, it may be that my definition of "tranquil" is not giving myself credit for the "worky" things I pepper my days and nights with, even in the midst of what I think is just hanging out, relaxing. I can be watching TV in the evening, with the laptop on the table or on my lap (typical night for me, basically), and will go from Metafilter over to some work-related web browsing, and back and forth seamlessly, even though it's 1:00 AM.

Two, the business had long been established already (though the previous owner had to do some reputation rebuilding in 2002-2003 when he bought it from a previous owner). So I really didn't have to go through any of the "startup phase" stresses. The store already had a "brand," an existing customer base, and staff.

Three, it's inherently my nature not to be an uber-Type A workaholic, at least not in the conventional sense. Yes, work stuff may end up bleeding into aspects of my home life (I log into our sales system countless times a day when I'm not at the store, to see how sales are going -- I'm assuming this is the equivalent of "calling in to see how the register is"), but I also do goof-off web browsing when I'm physically at the store, too. Life and work all kind of meld together -- it isn't for everyone, but it works nicely for me.

In a lot of ways, the months leading up to my taking over this business had more of a classic/stereotypical gung-ho, workaholic, never-really-relaxing tone to them. It seemed like there was always more crap I had to send to a bank or prospective vendor; more forms to fill out; more paperwork to file, etc.

I may be looking at a second location, in another city, later this year or next year. That will, in many ways, be a lot like embarking upon a startup business, because (due to the fact that it's a new city) there won't be an existing client base, a recognized "brand," or an existing staff. Then we'll see how this approach to work goes -- I have a feeling I'll be back in chicken-with-his-head-cut-off mode again. But it'll be kind of fun, and hopefully, I'll be able to look back and say it was worth it. So far, that's how I look at the preparation for buying this business.

Long story short: It really depends on you. As individuals are different, so are business owners.
posted by CommonSense at 4:39 PM on March 19, 2010

Best answer: Over the course of the last dozen years, I have owned several small businesses in Manhattan, still currently run four and have ownership share in a fifth. With the exception of my most recent business, most of them require pretty little of my time. Even with this most recent business being what I consider a time suck, I still work fewer hours than your average 9 to 5-er (my oldest business is 11 years old, and the rest, with exception to my most recent are over 5 or 6 years old).
I essentially work like a dog to get them open, and once open, have the staff and systems in place so that they require minimal input on my part. This has enabled me to live part time in Australia for several years (going over every couple of months for 6 weeks to two months at a time), and take vacations often.
I consider myself a lazy Type A. I am as lazy as i can be and can spend days doing nothing at all, but at the same time, I get restless if it's been a while and I haven't started working something new.

When I started out, I used to get stressed at essentially everything. Over the years, I have come to the realization that almost everything is solvable/resolvable, and almost always the worst case scenario when a problem arises is that something is going to cost me more money than I want to spend (knock wood). This has made me change my outlook somewhat, and be a more laid back business owner (in fairness, none of my staff would call me laid back, but thats more because I am a moody person in general, not business related).

At some point, I made the decision to step back from the businesses. I promoted from within and made trusted employees managers. There were/are mistakes, and I know that the businesses are not run as well as if I were there everyday looking over everything, but to me it's worth it for me to have more freedom. I know that there is pilferage, and that there is waste, etc. but I accept that as part of the price I pay for not being there . A lot of business owners would freak out over the thought of these things happening, but for me, it's the trade off. Also-I don't think I am a particularly good businesswoman, I just think I am good at setting up businesses that can run more or less without me and earn me some money.
posted by newpotato at 5:32 PM on March 19, 2010 [1 favorite]

My Dad owns an accounting firm, and most of the time he's pretty chill. Except for tax season (now) which is stressful just because of the vast amount of the work he has to do.
posted by kylej at 6:39 PM on March 19, 2010