Posts filed under 'She's the boss'
With everyone talking about career change these days, I thought it would fun to examine the work/life balance of those who’ve transitioned to some of the most coveted careers out there. First up, Erika Teschke, who in 2005 left her 10-year career as a legal professional to start her own dog walking and pet sitting business. I recently interviewed Erika by e-mail. Highlights follow.

[Photo courtesy of Erika's Pet Service]
Q. What’s your typical work schedule?
A. Mondays through Fridays I do dog park runs 5 hours a day, between 9 a.m. and 2 p.m. I also do about 30 minutes of stopovers during the week, where I feed and visit a pet that’s home alone, either before 2 p.m. or after 6 p.m. On weekends, I’ll do about three hours of paperwork and stopovers. I try not to work before 9 a.m. and past 6 p.m., but I have to be flexible on this if I have a pet that needs medicine or a walk at a particular time.
Q. How has your work/life balance changed since starting your business?
A. I definitely have more personal time now. However, the anxieties are different. Whereas being in an office made me a slave to the man, now I am responsible for everything: income, business success, client development, dog safety, responsibility as a walker, giving back to the parks I use, to name a few. I also have to be available for clients. At first I made myself available at all times when I was trying to grow the business. But now, since my clients and I have well-established relationships and they trust I will get back to them in a timely manner, I feel more comfortable making the evenings my own. I still work many weekends doing vacation stopovers. It is just the nature of the business.
Q. Still, a 30-hour workweek sounds pretty great. What’s the catch?
A. I make about $25,000 less than when I worked at the law firm. [Read the rest at NWjobs.]
July 10th, 2009
Hey, new and aspiring freelancers in Seattle! Curious about how other self-employed professionals in the area got their start and deal with the ups and downs of working solo? On Tuesday, June 30, from 2 to 6 p.m., Seattle tech startup Jackson Fish Market is hosting its first Small & Special conference for current and hopeful small business owners. The conference is sold out, but I’ve got two free tickets to give away. Read on to see how you can win them…
Speakers at the event include Babeland co-founder Rachel Venning, children’s book publisher Oliver Chin, web application developer Steven Bristol, and international wine distributor Jon Rimmerman. You won’t find any venture-capital-hungry bazillionaires here; all the conference speakers bootstrapped their way to profitability.
As for the day’s agenda, according to Donald DeSantis of Jackson Fish Market, “It will be one part inspiration, one part practical advice, and one part meeting new people.” In addition, all attendees will be entered into a drawing to win a custom promotional video for their business, courtesy of lilipip! studios and valued at $8,000.
To register for the conference (a deal at $25.00!), see smallandspecial.com. For more deets about the conference, see smallandspecial.com. If you’d like to throw your digital hat into the ring for one of the two free tix I have to give away, tell me about your business idea and why I should pick you right here in the comments. (Sorry, I won’t have time to collect email responses this week.) Thanks, and enjoy!
June 28th, 2009
Like everyone else, I’m looking for ways to shave expenses. Dinners, presents, movies out, and tickets for live music are now few and far between. If I need clothes, I buy used as much as possible (I’ll break for new undees, sneakers, and socks though). If I play with friends, one of us suggests eating in or going to a free event, like a book reading or a talk. European vacation plans with the boyfriend are on hold. You know the drill — the frugal freelance budget, only on steroids.
I’m especially psyched that this insurance agent helped me pick a healthcare plan that costs $1500 less a year but still covers the stuff I need covered. (By dropping maternity, pharmacy, and vision bennies, I save money — who knew!?) And I made the switch from cable TV to Netflix a little while back. Together, these changes save me $200 a month, which ain’t too shabby.
Still, each time I revisit the “Where I can save?” question, two monthly expenses that I don’t really need to be incurring jump out at me:
(1) The money I pay to have my house cleaned every 4 to 6 weeks (about $100, depending on how dirty the house is). This is a total guilty pleasure for me. But I hate to clean and rarely have time to anyway. Besides, I look forward to that one day a month when I sit on the freshly vacuumed couch, survey the tidy, dog-hair-free living room, and think “Ahhhhhh.”
(2) The money I pay to have a 40-pound bag of Buddy’s food delivered every 4 to 6 weeks (about $10 delivery charge each time). For some reason, picking up the dog food is an errand I’ve always hated. Usually I realize I’m out of kibble when the dog needs breakfast and an editor needs the article I’m working on. Also, those bags are dang heavy. So when I heard about a local delivery service, I was all over it.
Although I aspire to live leanly as possible — even if it means sucking it up and picking up my own mutt chow and mopping my own damn floors – I have a hard time letting either service go because these people are independent business owners. It’s a total thrill to not have to pay Comcast $60 extra a month or to tell LifeWise Health Plan where they can stick their stupid, plundering rate increases. But it does not feel good at all to take business away from another self-employed person. So I’ve decided that I’m keeping both services, depression be damned. Unless I have to start dipping into the dog’s food myself, I’m getting my house cleaned and my kibble delivered to my doorstep.
How about you? Are there expenses you feel you should cut back on but can’t bear to dump because you’d be contributing to another small business owner losing income?
February 28th, 2009
My email pal Ian Sanders and I are running simultaneous interviews with each other this week on how men and women approach the self-employed life differently and what we can learn from each other. Ian owns a creative agency in London and is author of LEAP! Ditch Your Job, Start Your Own Business & Set Yourself Free and Juggle! Rethink Work, Reclaim Your Life. He’s also a dad to two toddlers. Part 1 of my interview with Ian follows; part 2 headed your way tomorrow. You can read Ian’s interview with me on his blog.

Q. Do you think men and women are driven by different factors in business?
A. Essentially I think men and women are both driven by being enterprising; they may have different approaches but they want the same goal: success.
Q. What do you think self-employed women can learn from men?
A. As soon as we start talking about gender differences we are of course generalising! With that caveat, I would say women can learn something about having guts to “just do it,” which sometimes men posses to a greater extent. Having that self-belief to be bold. I think women are better team players than men, so when they are working for themselves it can be tougher if they are not part of a team.
Q. What do you think self-employed men can learn from women?
A. Self-employed men can learn a few things from women, as I think women can be more adept at juggling a mixed portfolio and have the bandwidth to handle the varied tasks. Men are better at one thing at a time (apart from me of course!). I think blokes can be good at going out and winning business but sometimes lack the ability to simultaneously be across everything, the trivial and the detail. Women can also be better team players – personally, I find working relationships with women co-workers can be more stimulating and fruitful than with men.
Q. Do you think either men or women are better (in general) at separating work and play and keeping a balance between the two?
A. I think men are better at separating work and play; women are used to mixing it all up. Incidentally I think that mixing it all up is the way forward, and I’m no good at separation.
Q. What is your single most important survival tip for freelancers and people making the leap to self-employment?
A. My single most important survival tip is Focus. Focus on building revenues; focus on one area of business at a time, then diversify and build once you have foundations in place; focus on delivery of a project. Because a project not executed is just an idea.
December 15th, 2008
Amy writes: I have a small boarding facility on my property. I board eight horses and I also live on the premises. I am trying to decide if I need to become an LLC. My concerns: If something does happen to a horse on my property due to my negligence, I don’t want to lose my house/land. What is the best way for me to go about this? I have spoken to my insurance agent and I am working on getting a policy in place to cover the liability, including an umbrella.
I answer: I’m no lawyer, but I would think an LLC would be a good idea since you’re dealing with people’s animals. As a I understand it, an LLC offers more protection than simply purchasing liability insurance. Here’s an earlier post I wrote on LLCs. And here’s a whole page on LLCs on Nolo.com that can tell you more. I suggest talking to other boarders to see what legal structure they’ve set up — as well as a qualified legal professional to get their recommendations.
Good for you for getting the liability insurance though. Hopefully you got business liability insurance and not a personal liability plan. (More on that here.)
August 27th, 2008
I know as small business owners and freelancers it may be tempting to hire or subcontract to friends who need work but may not necessarily have the right qualifications (or motivations). Before you do, you may want to consider some of the pitfalls and suggestions I mentioned in this article.
A marketing director I recently met was kicking herself for recommending a friend for a temporary position doing admin work for her boss.
“Everything started out OK,” said Christie, who works at an arts organization in San Francisco. ” And then the whining started.”
The job was beneath him, didn’t pay enough and wasn’t what he saw himself doing long-term, her ungrateful pal whinged. Then he told Christie that he “would be gone in a month or so.”
Only he didn’t quit. Instead, he stayed on nearly a year, “calling in sick once a week and showing up 30 to 45 minutes late every day,” Christie explained.
But the slacking didn’t stop there. There were the two-hour lunches, the “dental appointments” that required him to leave work early at least three days a week, and the maddening fact that he kept telling Christie about his necessary absences instead of dealing directly with his manager, something Christie was forever reminding him to do.
Read the rest of the article on abcnews.com.
July 11th, 2008
Hey Seattleites! My Seal Press comrades Emira Mears and Lauren Bacon — authors of this fine book you see to the left — will be in town this weekend for a book reading. The scoop:
Where: Elliott Bay Book Co (map)
When: Saturday, May 17 @ 4:30 pm
What: Book reading and signing, prizes, and a lively Q&A
I’ll be there. Will you?
May 15th, 2008
Lauren and Emira, authors of The Boss of You (which is getting rave reviews, by the way), are back with another guest post. A couple weeks ago, I was struggling with the question of business liability insurance — what I needed for myself as a company of one, and what to say about it in my new book. I asked them for their thoughts on the matter, and the result is this post. If you have any questions about small business liability insurance, feel free to post ‘em in the comments. I’m sure Lauren and Emira would be happy to answer.
For the first few years of our business life, we weren’t that concerned with liability insurance. While it would have been nice to take a “better safe than sorry” route, we didn’t really relish the thought of putting our meager earnings into insurance. At the time were a small company, without any staff, and our contracts state that we have no responsibility for our clients’ data and that our liability doesn’t exceed the value of any individual contract.
It was actually when we moved into our office space that liability insurance came up — our building required that we carry a minimum amount, as well as Errors & Omissions (E&O) insurance. Shortly after that we also hired staff, and while we certainly trusted our staff implicitly, things began to get a little more removed from our control, while ultimately if anything went wrong we’d be the ones holding the bag. At that point in time, we were really happy that we already had liability insurance in place.
Over the last couple of years, we’ve encountered a new situation with liability insurance that we hadn’t really considered when we first started out: we’ve been working with larger clients (particularly with government organizations) that actually require us to have liability insurance in order to be a successful bidder on any contracts.
We didn’t start our business with a vision of working with these kinds of larger organizations, but we know some people go into freelancing with the plan to work primarily with bigger organizations — often they actually come from having worked for a larger organization and move from a paid staff position to consulting after some time away, a maternity leave, etc. The point is, if you think you’re going to work with these kinds of larger institutions or organizations, you definitely don’t want to be trying to figure out your insurance while you’re replying to a 20+ page Request for Proposal. So, if that describes your target client, we’d strongly recommend getting some insurance in place from the get-go.
When working with larger organizations that are likely to require that you to carry liability and E&O insurance, you should work that into your pricing. With additional overhead expenses like that, you will need to charge more, simply because your cost of doing business (as required by clients) is significantly higher. So make sure you feel very comfortable charging enough to cover those expenses.
In our case, we actually went from working with an organization that didn’t require business liability insurance to that organization changing their policy (requiring us to carry insurance). And after that change, when we submitted our next quote for work at a higher rate than we had charged in the past, we made sure to gently remind the client that our rates were going up to reflect the additional costs they required we incur.
When you’re seeking out quotes on liability and E&O insurance, be warned that many insurance providers don’t really understand how to sell this kind of insurance to smaller outfits. They often have predetermined categories that are actually for bigger businesses. So it’s worth pushing back on your initial quote and making sure they really understand what it is you do, and what your actual level of risk is so you’re not paying the same amount as a firm with hundreds of employees that can technically be slotted in your category.
This is especially true for freelancers. When we first started looking for liability and E&O insurance, the carriers wanted to slot us in like we were a hosting company (we’re a web site design company), which is a whole other kettle of fish (hosting companies are explicitly responsible for their customers’ data for example, where our contracts state we are not). So we had to make the carriers understand what it is we actually do in a day, and what the real risks we carry are. And the price difference was significant.
Another piece of advice we always give on pricing and insurance is to try to renegotiate your policy annually, especially after you’ve held it for a year or two. We have a great insurance agent and she prompted me on this one initially, by basically saying, “You know I can probably get you more coverage for this premium since you’ve had no claims/are in good standing” — and she did. Now typically they don’t want to actually lower your premiums, because of course that’s how they’re getting paid too, but they will go to bat for you on getting you more for your money and that’s better than nothing.
May 10th, 2008
Are you a business of one who’s wondering whether it’s time to hire an extra pair of hands? Torn between whether you should hire an employee or a subcontractor? Fairly certain that if you don’t start delegating soon your head will implode, but not sure what tasks to farm out, let alone where to find a capable set of extra hands in the first place?
Not to worry. Lauren Bacon and Emira Mears are here to help. Lauren and Emira started Raised Eyebrow Web Studio, Inc. in 2000, so that they could be their own bosses and continue to work with the not-for-profit and small business clients they loved. They became so dang good at it they decided to write a book — The Boss of You: Everything a Woman Needs to Know to Start, Run, and Maintain Her Own Business. So without further adieu, here’s what Lauren and Emira have to say on hiring your first employee…
There comes a time in every successful self-employed gal’s life when the question arises: How do I know when it’s time to hire some help?
The first step is to look for the warning signs that going it alone is not working out. For most small enterprises, there’s a good long stretch where you (and your business partner, if you have one) are your only employee(s). Of course, if you’re successful, you’re likely to get busier and busier, up until the point where you stop being able to juggle all the work you’ve got coming in.
We hit this point in our business about three years in, but we didn’t see it for much, much longer. It’s our hope that our tale of woe will inspire others to act promptly when the time comes to bring in an extra pair of hands.
See, between client work and the administrivia of running our business (answering email and phone calls, managing our books, and so on), we found ourselves working longer and longer hours and feeling like we were getting no further ahead. We were losing our weekends at the office, and losing sleep over the prospect of missing deadlines if we slowed down. Our success was killing us — the more work we did, the more referrals our clients sent our way, and we couldn’t keep up with the demand.
So why didn’t we hire someone right then and there? Three big reasons:
1. Fear of financial risk. We were terrified that the moment we hired someone, our workload would drop off and we wouldn’t have enough work to keep everyone busy (and the business profitable). The thought of being responsible for another person’s salary on top of our own was just scary enough to make us hesitate.
2. Fear of change. We liked our little two-person, best-friends-and-business-partners-forever setup. And we knew that dynamic would change the moment we brought another person into the mix. We weren’t ready to step out of our roles as comfortable equals and into being the bosses of someone else.
3. Fear of losing control. Yeah, we were hardcore control freaks. (Or, as our hero Joss Whedon prefers to phrase it, “control enthusiasts.”) We were completely stressed out at the thought we might hire someone who wasn’t as perfectionistic as we were, and see the quality of our work deteriorate.
So where did that leave us? Stuck in overwork hell for another couple of years. Yeah, that’s right, I said years. It got pretty ugly; there were emotional breakdowns on both our parts on a fairly regular basis, due to too much work and not enough play, rest, and perspective. People kept telling us we needed to hire help and we kept arguing with them, telling them we didn’t want to grow, and that we’d find some other way to cope.
(Now, by the way, that’s a perfectly legitimate strategy, but only if you’re comfortable turning down work so that you can stay sane. We weren’t doing that.)
So how did we get over our fears? In short:
1. We discovered that not only will a hard-working employee pay for themselves (in our case, by working a reasonable number of billable hours per week), but will speed up production times (duh) and thereby quicken up the cashflow cycle (because when projects finish faster, the billing date comes sooner).
2. We hired someone we liked. A lot.
3. We peppered our job posting with phrases like “detail-oriented” and “meticulous,” and hired someone just as careful and quality-conscious as we are.
That’s the short version. There’s plenty more on the subject of hiring help in our book. But meanwhile, please feel free to post your questions about hiring here, and we’ll do our best to answer them.
May 5th, 2008
I am sleep deprived and drowning in deadlines. Posting will continue to be light until May 5th or so. For now, enjoy this freelancer-related randomata.
Here’s what happens when Homer Simpson decides to work from home. (Via Jezebel.)
Here’s what the New York Times has to say about charging your clients enough money. (Here’s what I — and some of you — have to say.)
Here’s what a recent study on individual health insurance found:
People who buy their own health insurance saw their average annual premiums rise 18 percent between 2002 and 2005, a modest increase compared to the 34 percent jump in average premiums for people insured through their employers, according to the latest News and Numbers from the Agency for Healthcare Research and Quality.
Somehow that didn’t make me feel any better about the 30+ percent increase in my health insurance premiums this year. After all, I don’t have an employer to subsidize the monthly premiums. Instead, I raised my deductible so I can afford coverage. Lame. But a common problem in this country.
Here’s a story that made me feel better about the above. This kind doctor quit the medical rat race and started a clinic that serves people with no health insurance. 40,000 patient visits since 2002. Nice!
April 25th, 2008
Previous Posts