Work for Yourself or Someone Else?

Now that my husband has been on his new job for a month, I ran the budget against his new income. The results were not good. We can get by, but barely. Fortunately we still have a pretty decent sized emergency fund to cover us until we figure out our next step.

Unfortunately, the new job isn’t going very well. Radio is slowly dying to mp3s and satellite radio, and the economy around here is tanking, so businesses aren’t buying radio advertising. That’s bad news for a guy selling radio advertising.

So we’re at a crossroads. Should my husband look for a new job? Or should he go into business for himself? Or both?

Shannon has a lot of experience in radio, both on air and off. He has a fair amount of experience in newspaper advertising, and even some experience in television. He loves writing ad copy, and quite frankly, he’s pretty good at it. I really think with enough persistence, he could be very successful branching out into freelance copywriting. The question is….do we dare?

So what are your opinions? What are the benefits of working for yourself? The benefits of working for someone else? Is there a clear winner here? Don’t be afraid to comment. Whatever the comments are, we’ll take them into consideration, but we aren’t going to take this decision lightly, and we certainly won’t blame my blog readers if we make a decision that goes bad. :)


By , on Sep 28, 2007
Lynnae McCoy I'm Lynnae, wife of one and stay-at-home mom of two. I'm committed to getting out of debt by being frugal with my choices in life.


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  1. Don Simkovich:

    I just came across your post via Google. You’ve heard of Google, right? Actually, I was about to post on this very issue on my blog. I’m curious. what have you decided?

    My background is also in radio, writing, etc.
    If he’s good at writing ad copy, writing online would be perfect and he could pitch to ad agencies around the country while maintaining his position.

  2. Lynnae:

    Plonkee, the healthcare is a big issue. We’re working on that now. If we can’t work that out, it’s going to be a no-go for sure.

    Dana, finding something my husband loves is the key. I hate to see him discouraged about his job.

    Boomeyers, I’ve thought about that too, but I don’t have anywhere near the earning power that my husband does.

    If this idea ever were to take off, I think my husband and I would make a great team. I’m good with details like record keeping, and he’s really good at copywriting, of course, and also in working with people. And cold calling. And collecting. :)

  3. Working for yourself on the side while maintaining your day job can be a good idea… you get the health benefits and such, plus you spend your time doing something you truly enjoy (in Shannon’s case, copywriting, but it sounds like he enjoys selling advertising as well), and you hopefully make additional money doing it. I’d love to work completely for myself… but until it’s a financial possibility, I’ll keep my day job and do everything else at all other times of the day.

    Copywriting is an *excellent* job for working alongside a day job because it involves solitary work. You don’t have to rely on other people to get what you need… they’ll provide you with the requirements, but as long as there aren’t many questions, you just do you own thing whenever it’s convenient, not worrying about whether other people are doing business at the same time.

  4. boomeyers:

    You have a magic secret weapon – YOU! You could decide to switch places and let your DH work for himself and you could go get the fulltime job that has benefits. We have thought about this many times ourselves, but I can’t make as much as he does, so not sure how it would work for you, but it is an option!

  5. dana:

    I have been self employed for about 5 years. i do love it . but it did not come easy. my hubby does work fulltime so if there are times when I slow down we know we can rely on his paycheck. I think you just have to do something that you really love!

  6. Paula:

    I’m so sorry you guys are in this position. I was under the impression that satellite radio was failing?

    I’ll keep you in my thoughts & prayers while you decide what to do.

  7. Lynnae:

    Wow! I leave for a few hours and come back to all this great insight! Thanks for your input, everyone. It’s great to hear from people who have actually been there.

    @Jennifer, thanks for letting me know that Oregon is particularly bad with the taxes. It doesn’t surprise me at all. :(

    @Paula, I don’t know that satellite radio is doing really great, but it’s taken it’s chunk away from regular ole radio.

    Shannon and I are both really cautious people, so there’s no way we’d jump into this without a strong safety net. This is all really preliminary, and at this point we just want to see if this is even an option for the future.

  8. To be honest, I couldn’t cope with that level of stress about healthcare. But otherwise – go for it.

  9. Hilda:

    Oh yeah, here in my town, I heard the radio station advertising to businesses. It goes something like “so you have an excellent watchamahooddie but nobody is buying it? It’s because nobody knows about it. You need to advertise in your local radio station!” It sounds catchy and very funny. Maybe Shannon can use some advertising like that.

  10. Hilda:

    I agree with the posters above. Keep the job for now but start a side business, too. Being in business for yourself has a lot of tax advantages. However, the amount of income is not guaranteed and until he’s positive the whole family can live off the business, it’s prudent to keep a day job. I really hope everything works out for your family.

  11. April:

    I agree with the advice – do both! My husband has a regular weekday job and does freelance website design/programming nights and weekends. He spends a LOT of time on the computer, but it really helps make ends meet!

  12. Lynnae:

    Jaimie, that’s exactly what we were thinking we’d do. We know we’re not in a position for him to go full time with this yet, but it’s what we would be working toward. My husband is really good about doing whatever it takes to keep the family afloat, so I know he’ll work whatever job he needs to to make sure we can pay the bills.

    And fortunately this is something he could easily do on the side, until business takes off. We’re researching right now. He has an appointment with a guy who runs an ad agency to see if this kind of work is in demand. They have a good working relationship, so I’m sure he’ll get an honest answer.

    Erin, thank you for the good thoughts. We can use all we can get right now. :)

  13. Kyle:

    Wow, you got some great advice in the comments section. When I started my own business I did a lot of the work at night and weekends and kept my regular job until my business grew to the point where I could make a better living working full time. Takes hard work and patience but it can be done. It sounds like your husband has the talent to do it!

  14. Do them both…Kris is getting set up to start recording again and giving guitar lessons. If it takes off he could do that full time for twice as much money as he makes now but if he does it part time when we have some available time for him to work on it he’ll bring a hefty amount of extra cash…so it’s a win~win situation!!

  15. We’ve been in those shoes. The difference being that we hung on until the bitter end of the job, using up whatever resources we had to try and make it work. When we finally made the decision to move in a different direction, it was a decision made in desperation and a huge amount of debt.

    Having said that, we are both working for ourselves now, and I wouldn’t want to go back to any other way of working. I love the control it gives us – if it’s a hard month, then we’ll both step up the marketing and contracting until we’re ahead of the curve…

    My advice is not to hold onto the employed lifestyle until the bitter end, and then be faced with a stark choice with no money or time to support the other options.

    If S. wants to go for it, then start copywriting in the evenings and at weekends to build up a client base, whilst keeping the radio job on. It shouldn’t take too long to get a feel for how things are panning out.

    Follow your dreams – if you’re happy, then you’re doing it right :-)

  16. Having worked for myself and for others, I would not work for myself as a sole source of income, unless I had very lucrative savings & investments that were bringing in enough money I could live on &/or supplement my income until I die.

    Especially when you consider the financial implications of retirement, social security & health insurance without employer benefits. I would recommend he get a job in an industry that is not tanking, while also putting out shingles on the side to build up his own business as well. Then as his business becomes reliable & successful, start cutting back on the “day job” if you want. You have to make at least 30% more money working for yourself to cover what you lose in benefits working for someone else, and insurance, social security, etc cost more when you are subsidizing the whole thing. Example-my husband’s employer pays $500 every 2 weeks for our health insurance. We pay $100. If we were to buy our own insurance, we would pay that entire $1200 a month, plus the coverage wouldn’t be as good because there are some coverages that only come with group plans. For example, where I live there is no insurance policy you can buy privately that pays for maternity and some other important coverages. Social security you will pay twice what you are paying now, because right now your employer is supposed to pay half. And some states have very high self employment taxes which can hit you as well. Oregon is a state that is particularly bad, but there are others, so look around to see if you are going to double your tax burden to work for yourself as well.

    Other options you have are downsizing more to be able to afford his current salary, or finding a job in a different industry.

  17. Well, okay. This is what I think.

    Establishing a business takes time, and you have to be able to kind of…. let it flounder at first (from a financial standpoint) as you build it up. And it doesn’t sound like you’re in a position to be able to do that right now. I think at the moment, the best option is to keep looking for a better job as you pay down debt and keep as much of your inheritance windfall earning interest as possible.

    But – could Shannon do the copywriting on the side somewhat and use it as supplemental income while establishing a client base? then once he has enough clients, he could break out on his own knowing that he could provide for his family that way.

    I dunno. This may make no sense but it is what was in my head.

  18. Erin:

    I’m sorry, I don’t have any advice about working for yourself. But I do hope that things get better for ya’ll, changing jobs can be so stressful.

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