How to find work with a flexible schedule

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Most of us think of a dream career as one that affords us flexibility for personal relationships and high engagement for personal growth. And while flexible work used to be limited to women, USA Today reports that increasingly, men, too, feel stress from the personal impact of inflexible work. So the question for everyone is: What’s the best path to get this dream career?

Retail is a great way to get flexible work, (which is why I think we should see a surge in educated people taking retail jobs.) But most people don’t aspire to retail because the work is not intellectually engaging. On the other hand, most of the intellectually challenging work in this world comes with inflexible schedules.

So the trick is not to get flexibility, the trick is to get it without losing engaging work and avoiding a pay cut. Also, keep in mind that flexible work is not about the hours, it’s about control. Because most of us are fine with working long hours as long as we have control over those hours.

Given these parameters for thinking about flexible work, here are the tricks for landing that sort of job:

Be a star. There are great stories all over the place about women who negotiated. Brenda Barnes was CEO of Pepsi, then she quit to take care of three kids. She came back and took a position as CEO of Sara Lee. That's the ultimate flexibility: A CEO position in the Fortune 500 with seven years off to raise kids. But who is as talented in business as Brenda Barnes? Not many of us. The flexibility you can negotiate is directly commensurate to the star power you established before you started negotiating.

Be relentless. Flexibility comes, usually, after proving your worth to a company. Which means you can't job hop to get flexibility unless you're a rock star and can make it a precondition for hiring. Non rock stars need to stick around longer. Prove your worth, and then make tons of suggestions to get the specific flexibility you want—a new department, different hours, less travel, on-site child care, maybe a satellite office near your home.
You need to propose options that are solutions for you. And if one doesn't work, try another.

Know your bottom line. I wouldn't work without enough money to have household help. It was a precondition for me being available at all times to the company—I needed household available at all times to me. This gives me the ability to create the type of flexibility I need in my life. At one point, things got so tenuous that I had a huge screaming match with one of my investors over my salary. But I didn't budge. I had the confidence that I knew my line in the sand, and I wasn't going to cross it.

Gear up for big risks. Screaming at my investors. And crying. And getting thrown out of the attorney's office where we were. Those were big risks. I could have lost my company. But I didn't. And I didn't lose my salary either. But I took big risks. You never know what risks you'll have to take to get what you want. But it's safe to say that if you are aiming for flexibility in corporate America, you will need to risk your job, or your salary, to get what you want.

Be careful what you wish for. If you win the flexibility to do your work when you want to, and you make space in your day for your kids, you still did not get more time in your day. For example, it's clear to me that there's a surge of email from 9pm — 11pm eastern, as kids across America go to bed and parents jump online. So we're better parents and engaged workers, but Oprah magazine reports that more than half of people who are married say they don't have enough time for their spouses.

57 replies
  1. GregoryDopka
    GregoryDopka says:

    Jack Welch also talks about work-life flexibility in his book, Winning. He refers to the ‘chit’ system where you earn chits for great, consistent performance over time. You then can trade in chits for flexibility.

    • malingerer
      malingerer says:

      Jack Welch.. now there’s an example of how one should live their life.. not.. what a douche bag.. Sorry, but no brownie points or chits for that comment.. If all you read is his on drivel then you are far from being educated on his values..

  2. KateNonymous
    KateNonymous says:

    Retail may be a great way to get flexible hours, but the lack of intellectual engagement isn’t its only downside. You have to deal with customers, which not everyone wants to do, and you don’t get paid a lot.

    But I’m glad to see the emphasis on proving oneself. Most people don’t understand how long that process takes, and expect the benefits almost immediately.

  3. Hope
    Hope says:

    “Screaming at my investors. And crying. And getting thrown out of the attorney's office …”

    In my world, this is called lack of self-control. But I’m not a big risk-taker.

  4. Adam
    Adam says:

    As a happily married father of two, your commentary on the surge of e-mail from 9-11pm and the impact of this on spouses really resonates. Each night my wife and I sit with our laptops on our laps finishing our work for the day and preparing for the following day.

    It is important to continue to find “quality time” with your spouse while balancing everything else or eventually you’ll wake-up and realize you hardly know each other.

  5. Wendy
    Wendy says:

    Great post. Implicit in your examples, but not explicitly stated is that flexibility is a “two way street.”

    Most employers that offer flexibility will expect it back from time to time. For example, most days you can leave at 3 to get the kids, and then work after they go to bed or settle in to work on their own homework. But a big client in town, or other priority projects may occasionally require that you stay later. So, like Penelope, you still often need the household help arrangements to allow you to be flexible too.

  6. Shefaly
    Shefaly says:


    Good points but I wouldn’t call “..Screaming at my investors. And crying. And getting thrown out..” risk-taking. Just plain risky. The kind of behaviour that will get a person the ultimate flexibility of all: never to have come to that job at all (i.e. be fired)!

    Working for oneself is, of course, the desirable kind of flexibility model. However the exact model that works for anyone depends on the reasons why they seek flexibility. People who are main carers to their kids need a different kind of flexibility, from people who are main carers to their ageing parents, and from people who may choose flexibility to support a spouse to pursue a dream or a demanding job, or from people who just cannot function in an office type environment. Some choose flexibility for variety and control, others for working fewer hours.

    So the zeroth factor in seeking flexibility would be: “Know your reason”. For it impacts all else you seek to do to achieve that flexibility.


  7. Caitlin
    Caitlin says:

    Are you sure you are cut out to be an entrepreneur? I thought it came with the territory that in the early days you are working for equity but little or no salary. Yet you are drawing a big salary (big enough to afford household help anyway) and when the company runs out of cash, you don’t pay contractors (as per a previous post). Something doesn’t sound right there. If I were an investor, I’d probably be screaming too! But I guess they agreed to all that in advance, so good for you for getting it.

      • econobiker
        econobiker says:

        Yeah, I thought that too.

        But that is how most d*ck entrepreneurs get ahead- by screwing over someone else worse than they get screwed…

  8. prklypr
    prklypr says:

    Way back in 1989 I negotiated a flexible schedule at a company that had never even had a top exec become pregnant and take maternity leave. In return for a 20% pay cut, I cut back to a 4 day workweek. But since there was no one replacing me on the 5th day, I just crammed 5 days worth of work into 4 long days – for less pay. It was a sacrifice I was willing to make at the time. This was before telecommuting and working from home were popular; your presence in the office was noticed, and I was often the recipient of snide comments from my {mostly male} coworkers about things I had missed on my “day off.” I eventually quit when the company was sold and the flex-time policy I helped create was not supported by new management. Things have changed a lot in 20 years.

  9. GInger Rose
    GInger Rose says:

    Most people don’t aspire to retail work because it’s not intellectually engaging AND because it pays shit wages AND it can be physically exhausting work.

  10. Laura
    Laura says:

    Great post Penelope! As a new reader of your blog – I really appreciate the sound advice.

    Re flex work schedule – my current company – Sun Microsystems – wrote the book on how to support the flexible work environment. If you check out – you can find all kinds of great bits/pieces on why it makes sense for the company’s bottom line – and why it makes Sun a great place to work.

    (or did – unfortunately – we are in the process of being acquired by Oracle – so I may find myself looking for a new job very soon.)

    Do you or your readers know of other companies like Sun who really advocate for this open style/open work place?

  11. Will at Virtualjobcoach
    Will at Virtualjobcoach says:

    Ugh, bad superficial advice (and drama!). I mean, ‘cmon, “be a star”??? “work retail”?????

    How about doing the following:
    1) determine if you do the type of work that can be performed during ‘non-standard’ hours or remotely. Some professions, you cannot work remotely but can work non-standard hours whereas others you can work remotely but have to be on standard hours. The latter is increasingly common in tech companies.
    2) determine if you want non-standard hours or remote work, both can be used to have more ‘family time’ and schedule flexibility.
    3) determine your ‘ideal’ schedule. Do you need 1 whole day to interact with your spouse/kids? Half a day? Two lunches a week? Basically, understand what your requirements are before you go testing the waters.
    4) make your ideal schedule realistic. Yes, your ideal schedule could be to work 1 hour a week and get paid for 40, but this is clearly unrealistic. Take into account your roles, your responsibilities, requirements for co-worker interactions (face to face), company culture and pretty much anything else that may effect your ability to work off-hours or remotely.
    5) see if your company has a policy on off-hours/remote work and understand its nature and restrictions.
    6) Compare 4 & 5, if they synch then you are golden, however just because it is OK with HR doesn’t mean it is ok for your manager. Realize that when push comes to shove, that your manager will likely yield to HR policy, but it will likely get your career progress knocked down a few levels (or put you on the layoff list)
    7) if your company doesn’t have a flex-time/remote work policy then “build a business case” for why you should have one and be very specific about what you want (don’t say “I want a more flexible schedule” but say “I propose that I leave at 3 four days a week and those days I will make-up this work by being available from 8 to 10 pm. The business case is to prove that your flexible schedule won’t have a big downside to the company.

    Finally, there are many areas of work that offer flex-schedules aside from retail. Single shingle consulting is one, if you don’t have to be on-site then you can set your own hours. Other areas to explore are those where you are responsible for the deliverable but how you get there is up to you (time spent, etc.). These types of jobs are not uncommon and can be ‘designed’ by professionals.

    IMHO of course :^)

    • econobiker
      econobiker says:

      Or become a power blogger telling people how to do the above and write off vacations by scheduling them concurrent with speaking engagements along with employing your spouse as part of your company…

      Everything is paid for by customers or vendors and all other costs written off as business expenses…

      “Combining life with work and bending the tax system to your benefit the whole time…”

  12. Ron
    Ron says:


    Yes. Great post. Enjoy your style.

    I do have to agree with the Jack Welch comments. I’ve read several of his books and comes off like a screaming tyrant whining for attention. He likes to fire the bottom 10% of his staff every year.

    I bet Friday afternoons at GE were made for “Depends”.

    Great work,

  13. jenx67
    jenx67 says:

    Reason #354 Jen blogs about generation x: In 1998, I wanted more time with my newborn – more time as in leaving work at noon on Fridays. I was a star performer. I had a nearly 10 year track record of results. My Boomer employers would not relent. So, I found a new job, where they would give me half days off every Friday and Wednesday. It was at a university. I signed a contract. Then I resigned. When I told my bosses they said, “We were about to offer you flexibility.” But, I’d already signed that contract. But, in that contract, I didn’t outline my flexibility terms and the first day on the job, my new Boomer boss said, “Let’s not start that half day thing for awhile. I don’t think it will go over well with the other employees.” I was sunk. I never did get the half days off.

    Last May, after 18 years of no flexibility and star performance, and 10 months following the birth of my third child, I quit my high-paying job in PR. All my Boomer employers wanted to offer me was money, and all I wanted was a little more time – to clean my house, run errands, plan a shopping list, attend a school program. I was willing to give up thousands of dollars for this.

    I almost didn’t read this post, Penelope, because for me, the emotions this evokes are very raw.

    • thatgirlinnewyork
      thatgirlinnewyork says:

      from another x-er, i thank you for sharing this! for years i’ve endured the hypocrisy of boomers who leave for their kids’ _______ (fill in the blank–baseball games, doctors’ appointments, etc.), but who would look at me cross-eyed if i needed a half day for a domestic issue (or, god forbid, a day off). i don’t have children–i haven’t been able to. but i have a husband i adore, and a life with him that deserves attention, as he is my family. think i can tell my boomer higher-ups that i need time for him (he is a professor, with far more flex hours than i’d ever have as a corporate wonk)? i know how that conversation would turn out, so i’m resigned to fibbing my reasons when i get up the nerve. this seems so counter-productive when i have four weeks of vacation i cannot use in any meaningful way.

      but it seems that having children doesn’t even allow one to advocate on their own behalf, and i salute you for kicking the inflexible to the curb. i, too, would trade the dollars for more personal time, but that kind of bargaining, obviously, was not taught in the mba programs these freaks all went to in the 80s (too busy studying useless, now-dated theories like TQM and such). can you post your blog name without reproach here?

  14. Leigh
    Leigh says:

    Great post Penelope. There are as many ways to wrangle flexible working hours as there are people trying to do it, but you’re right, the trick is to do it without losing the engagement or pay. There are some great resources on how to find flexible work and live wherever you choose on It’s definitely worth checking out.

  15. Tiffany
    Tiffany says:

    I enjoyed this article, just for the fact that its from ur personal experience & does not regurgitate what most flex schedule article say. So, cheers to you on that. And like some have eluded to, being flexible is so situational. I did do retail a couple of times just to spice things up when it comes to the contrast of office life to the real world of bastards that don’t pretend they like you. The pay was not as much as I would get in an office but I did like the different hour choices. Working in corporate america & trying to form a flex schedule is friggin hard but I can’t think of another place where its always worth it to seek it out or try to build one.

  16. Maureen Sharib
    Maureen Sharib says:

    Barbara Walters said somewhere a while ago that a woman can have two things out of three – two but NOT three. The three things a woman has a chance at having only by limiting herself to two are:
    Thoughts on that musing appreciated. Personally, I think there’s much truth in it.

    • KateNonymous
      KateNonymous says:

      I would say that a woman can have all three if she has a stay-at-home spouse, or makes enough to hire someone to do everything she’s not able to time-wise. After all, men historically haven’t had to choose among those three. But women generally don’t have wives.

  17. Jeff T.
    Jeff T. says:

    Will’s comments above are right on.

    Longer hours but higher discretion on WHEN you spend the time is the modern flexibility. Many big company business jobs are now “International” which means that middle managers sacrifice either end of their day to talk to Europe (in the morning) or Asia (in the evening) but gain a lot flexibility during the middle of the day.

    Some of this is just conformance to reality – you can’t expect someone on that weekly 11 PM conference call if you demand he be at work at 7:00 the next morning – but you can make this work for you. For instance, no one blinks if I leave work at 3 to attend my son’s football practice these days. That was unheard of 20 years ago.

    Of course the same people will hear me comment on our supplier issues in Suzhou on the 10 PM status call and my wife and kids are wondering why I lug my laptop to the breakfast table.

  18. MeredithElaine
    MeredithElaine says:

    Most people I know who have retail jobs right now, are working TWO jobs. One of my friends works part time at a clothing store because she’s not getting by from her job at a bank. Another took a job as a server on top of his retail job.

    Two jobs leaves little time for anything else…where’s the flexibility there?

    One took a retail job to supplement her income. One took on another job because his income in retail needed to be supplemented. I don’t think I know anyone who works retail as a full-time gig and is getting by on what they make.

    I loved working retail back in the day. I would have stayed with it had the pay not been so terrible. I made $2 more per hour working in hotel reservations, and a few more dollars per hour as a receptionist.

  19. Savvy Working Gal
    Savvy Working Gal says:

    I have a friend who wanting a more flexible schedule and less stress took early retirement from her teaching career two years ago. Since, she is a very social person, she still wanted to work, but in a less stressful, part-time capacity.

    She now regrets her decision and can't help wondering if it's all been worth it. First, there was the process of finding a new job which wasn't as easy as she'd thought. After several months of filing out job applications and waiting for interviews, she found a job working as a cashier at her local pharmacy. She found working with the public was more trying than she'd thought. Also, mastering the pharmacy's cash register was not an easy task. Despite working fewer hours, she still finds herself working with difficult people and dealing with work-place politics, only now she makes less money and has no benefits. She thinks she may have been better off staying where she was at. She knew her old job like the back of her hand. This summer accepted a part-time teaching job at her old school in addition to her retail work.

  20. Freelancer
    Freelancer says:

    Screaming and crying in a meeting to get your way? Can you imagine what people would say if a man did that? Regardless of gender though, it’s totally unprofessional behavior and even if you get your way, it would have to leave a lasting impression on everyone else in that meeting. There are other ways to negotiate, maybe worth investigating.

    • Brad
      Brad says:

      But, apparently for PT, screaming and crying actually works. It achieves her desired end, making it a legitimate negotiation tactic. That’s part of what makes her company so surreal. I would love to see a post from one of these investors, explaining why they think Brazen Careerist is the place to put their money.

  21. Andrea
    Andrea says:

    For people who are married, particularly those with kids, the other key piece of getting flexibility is making sure your spouse is an equal contributor. There’s a great new book I’ve read called Getting to 50|50 that provides compelling evidence of how everyone is better off, parents, kids & employers, when your spouse is an equal partner.

    The tougher, but also important step that needs to be taken is for employers to get more comfortable embracing flexibility. Face time does not equal output.

    • thatgirlinnewyork
      thatgirlinnewyork says:

      anyone who thinks that absolute equity is possible is dreaming. much of the effort each in the couple makes is not quantifiable. an example: a friend of mine is a stay-home mother with a nanny 20 hours a week, and a cleaning woman once a week. she teaches one class that takes her away five of those hours. they keep her job for insurance, but ultimately, all their “operating income” comes from the husband’s business. yet the wife in the equation thinks she’s “doing more than her share” because her husband works a 60 hour week, but comes home to be a present, participating father evenings and weekends. the wife wouldn’t dream of going out and working a 60-hour week, so again, if a couple has to sit down and plot their “contributions” to a marriage such that they can be quantified, they have bigger problems than a flexible work schedule can solve.

  22. Kate Robins
    Kate Robins says:

    Screaming and crying doesn’t work for my kids or reports. I don’t want to be an employee’s mother. There’s a glut of overqualified people and a dearth of jobs. I don’t have a glut of kids at home and I can’t fire the ones I’ve got. I can only do my best to make them decent people.

    With employees, screaming and crying is beyond my control. I’ve had reports who tried that, embarrassed themselves, and left empty handed. I improved my candidate screening skills.

  23. Jim Taggart
    Jim Taggart says:

    You hit on a number of important points. It’s not that retail work is intellectually unengaging, it also pays crap. A lot of people (like myself) who’ve worked in large bureaucracies a long time might say that things like telework and alternate work arrangements add flexibility to their lives. Or young people who work for companies that provide the bells and whistles of gadgets, in-house games, etc. and who let them arrive at work late (but work till midnight, sometimes sleeping at the office) might say that this is flexibility.

    I’d prefer to see it as are you as an individual able to empower yourself in your work, where you can show initiative and be rewarded; contribute to and/or make decisions; are listened to by your boss; and respected and not manipulated by management.

    Here’s a very cool site I discovered yesterday. Read the sample chapter her new book:

  24. Pirate Jo
    Pirate Jo says:

    I’m surprised no one has mentioned temporary, contract-based work yet. Accounting, finance, and IT have lots of those opportunities.

  25. techygirl
    techygirl says:

    At microsoft you can actually choose to work wherever and whenever you want… the whole campus is a hot spot for wireless, and if you take a trip, you can work from the local offices at your travel destination if you choose to.

    I will try to find the video I saw about Microsoft interns where they talked about this… I’ll post it soon….

  26. Liza
    Liza says:

    So, just to state an obvious;

    You refuse to take a salary that doesn’t allow for household help, yet you are an entrepreneur. …Don’t more start-ups, start broke and the owner doesn’t really see a reward for the first, oh I don’t know, year or so?

    I must ask, who is paying you to run a company with a salary that high and you are out begging for more money for the company????

    Maybe it isn’t any of my business, but that conflicts with what you and Brazen and your Entrepreneur Brand is all about.
    Or maybe you weren’t clear about the fact that you were possibly reflecting on previous jobs where you were not the CEO?

  27. Albion Pacific
    Albion Pacific says:

    I’m a bit puzzled by the idea that retail is of necessity not intellectually engaging. I worked in a bookstore for 22 years and found it terrifically engaging, must more so than most of the administrative roles I’ve had since. It was enormous fun to talk to people who read. They tend to be smart.

    Of course there are little shits that you have to deal with in retail, just as there are in every line of work but I think of all those interactions as part of a bell curve. One the one end are the (relatively few) utterly horribly customers, one the other end are the (hopefully more) completely delightful customers who bring you gifts both intellectual and real, and in the middle are the bulk of just plain interesting readers.

    Great fun.

    So why did it end? For the same reason you’re reading this — the arrival of the internet, and most specifically Amazon.

    • KateNonymous
      KateNonymous says:

      I suspect most of us aren’t thinking of bookstores, but of places like Macy’s or Target or Pep Boys. You’re right that there’s more to retail than that–but an awful lot of retail falls into that category.

      Actually, it would be interesting to see other exceptions.

      • ScottS
        ScottS says:

        I have a very part-time second job working at a small wine shop. Tasting and selling wine is a great retail job! As with Albion, most of our customers are quite fascinating and several have become friends. The shame of it is, the store is closing at the end of the month, so there goes my discount wine.

  28. Andrew Van Dellen
    Andrew Van Dellen says:

    A great post about a very great topic. I agree 100% and hope you don’t mind me linking to your post in my post of a similar topic. I am glad to see more people pushing for workplace happiness and employee centered employment!

  29. ION Consultants
    ION Consultants says:

    This is my dream job! Currently I work at an insurance company, but have my own consulting business on the side. Whenever I get a day off from the insurance company, I work on my consulting business and it is sooo refresshing to et wrk complted without someone breathing down your back.

  30. shelenbrook
    shelenbrook says:

    You hit the nail on the head. I’ve worked for the last 7 years (with two different companies) in flexible arrangements: reduced hours (32) plus remote days. I took a cut in salary, but it’s been worth every penny. I don’t miss anything my kids do, I clean the house and do the shopping.

    How did I get it? I said it’s what I wanted. After working for 7 years as a “star” player, it wasn’t hard to convince people to let me do it.

    Snide comments from the co-workers? Sometimes. But as soon as they learn I traded some $$ for the flexibility, they leave it alone.

    Oh – and I do manage to find time to spend with my hubby, who does the other 50% of housework and homework that I don’t do….

    It takes a lot of energy to juggle and balance it all, but the sacrifices I’ve made (money and sleep, namely) have been in the name of raising up 3 great kids without having to totally give up myself. I’m grateful to the women before me who paved the way. I hope I’m doing the same for those who follow.

  31. Lance
    Lance says:

    I achieved a good measure of flexibility in my work schedule but I had to loose out on benefits from my company to get it. Basically, they dropped me to “part-time” status even though I work full-time. The reason I did it was to be able to make my own schedule and build up my freelance business and get to a point where I could do that full-time. Eventually, I’ll only do freelance for my company and charge them 5x what they pay me now. At least that’s the plan.

    I found out today Netflix has an interesting open holiday plan, where you can take as much vacation as your want, when you want it. Best Buy has something similar, too.

  32. Will at Virtualjobcoach
    Will at Virtualjobcoach says:

    Re: Netflix and BestBuy ‘flexible holiday schedules’. I am guessing that they are doing this to cut headcount expenses more than offer a more flexible workplace. Usually, they first offer the ‘time off’ (with a cut in pay) if they don’t get enough people then they start selecting people. It is not dissimilar to ‘forced shutdowns’ that many manufacturing plants have during the holidays.

  33. says:

    Great post.

    I find having control over my own time is the best part of my job. But I work my ass off more than I ever have. To me, it’s worth it. I’m not paid for my time, I’m paid for what I accomplish.

  34. Terry Neese
    Terry Neese says:

    Great suggestions! It is unfortunate, though, that it is so hard to convince employers that flexibility will work for both parties. Companies can save thousands of dollars annually by allowing their employees to stray from the traditional forty hour work week. Many people would gladly give up hours to be allowed to spend more time with their families. In addition, many jobs make it possible for people to work from home, allowing the company to save valuable office space. Companies need to reevaluate their needs, and determine what they can do to both make their employees happy, and reduce spending. Businesses in the private sector should also be allowed to let their hourly workers choose comp time in lieu of overtime pay. The federal government allowed their hourly workers this option in 1978, but it is still illegal for the private sector. What's wrong with that picture? The federal government should allow private sector businesses as much flexibility as possible so that they can still thrive in this economy.

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