8 Questions to Ask before Quitting Regular Job to Work From Home

I quit my full time job last week! I have been working in the Software Industry all these years – 19 years to be precise – which is considered to be a high salary career in our context. As some of you already know, for the past few years, I have been experimenting with Internet marketing as well and it was getting really difficult to handle both these vastly varying careers together. Finally, I decided to quit my full time job in favor of the Work From Home option seeing the opportunity of making a good living out of it while working for lesser number of hours.

For those who kick-start blogging as fresh college pass-outs (or dropouts) – for that matter even for those who just started their career – it may not be a big issue to decide on a Work From Home career. But for someone who has to retire after all those long years into a full-time job, it is something BIG. Apart from planning for retirement (read my recent post on retirement planning) one needs to ask himself/herself a few questions before making such a big switch to freelancing or WFH opportunities.

Ask yourself a few questions…

A good readiness check to move to lucrative (but risky and unpredictable too) work at home career – especially in the online niche – would be asking the following questions.

Question 1: Have you planned for your Short-term money needs?

When you make a switch to Freelancing or WF, your monthly fixed and predictable income is going go away instantly. Even worse, it might take a few months before you start accelerating well and making money for yourself in your new life. Needless to say, you need to have some money in your checking account to meet your family budget demands.

A good thumb rule would be to have at least 6 times your family’s monthly expenses in your checking account.

Question 2: Have you Covered your Family for Life and Health Insurance?

A permanent job comes with a lot of benefits like some amount of accidental insurance cover and more importantly the medical / health cover for your family. Once you decide to quit your fulltime job, you have to make alternate arrangements for your family’s health coverage. This is very important as health related expenses are shooting up at an alarming pace and you don’t want ignore any potential huge expense item under that ticket.

Question 3: Are you fine with Loosing Perks and Benefits from regular job?

Apart from the salary, your company may have offered you a lot of perks and other benefits such as stock options, fuel reimbursement/allowance scheme, free cellular phone connections, leased cars and a lot more other benefits. By leaving the company to be on your own, you will lose some of those benefits and they can monetarily impact you.

You may have to make arrangements on your own before going the freelance or work-for-yourself route.

Question 4: Have you planned to Take care of your Training & Development needs?

Often companies invest big money in training and developing their employees. These trainings take place as and when there is a business need or certain technology or system change occur. Company sponsored training programs are a huge boon for employees as they keep their talent and knowledge up to date.

When you are going to be your own boss, you will foresee these needs, plan budget for the same and undertake your training programs without fail. Otherwise, you are going to be soon outdated and stale.

Question 5: Have you done some amount of post retirement planning?

When you retire from your Fulltime job, that also comes with certain amount of money that you saved up in your retirement plans (Pension scheme, Provident fund, 401-K or whatever). You need to do some amount of planning in such a way that, your retirement money can be safely invested in low-risk and regular return schemes so that it can supplement your freelance for WFH income.

Question 6: Is your secondary skills or freelancing job good enough to make a living?

This may sound like a silly question now that you have decided to take that route. However, one needs to do proper analysis (preferably with pessimistic estimates) on the kind of income it can generate, how much you can accelerate and peak yourself so that such a supplemental income can meet the financial needs in future.

Also, there has to be proper analysis done whether you are trying to make money out of your core skills, secondary skills or something that you think you are but you aren’t.

Question 7: Are you ready to do time management?

This is a big issue with many who opt for working from home. The number of distractions and lack of a proper schedule may be a huge issue when you work from home. Also, additional burden on chores, baby sitting or sharing tasks can sometime affect your throughput along unexpected proportions.

You are ready to work from home when you are great at time management. This is true for regular job too but more often than not, you have someone to monitor that part and pressurize you.

Question 8: What’s your Plan-B?

Now, just in case things didn’t go the way you want after a year or two into your freelancing or Work from home job, you need to have an alternate plan in mind. It would be good to have that plan in mind as well before taking up Plan-A, just in case.

Personal experience

Listed above are some of the questions that asked myself before making a complete switch to a WFM job recently. In fact, I have been doing that readiness check for a couple of years now. I hope that with all that planning done, things are going to be smooth for me in my work from home job of online marketing and blogging.

And, please do drop in with your comments or other questions that I might have missed above.


  1. Wow Ajith, congratulations on the major step. I did this 13 years ago and I wasn’t close to being as prepared as you are now.

    Working for yourself offers a lot more freedom but it also offers a lot more responsibility and thought. Initially I was sometimes working 18 to 20 hours a day as I was creating things; that’s a must. Then at some point I realized that I needed to start pushing certain things to other people so I could concentrate on my own stuff, such as hiring an accountant and someone to cut my grass. I wanted to hire someone to help clean the house but my wife doesn’t like that lol Still, it’s important to realize that you might have to spend some money to have time to make money.

    Best of wishes to you,. and if you have any questions about business in general, just ask. As for making money online… you da man! 🙂

    • Hi Mitch,
      Thank you for the wishes. Yeah, I had to take this call which was long pending. While my current online income is not matching the salary, it’s getting very closer and I hope I get there soon.

      Thank you for your support – will definitely be in touch with you when I am stuck with the typical business challenges 🙂

  2. nice sir,,,i will definitely looking more post from you sir.

  3. This is a good post and while I am not planning (yet) to move out of my day job to focus online, I also have that checklist that I constantly check to see where I’m at. I agree about your point that it takes a long time to ready yourself for this and even then there’s plenty of risk to take even with all the money saved from work.

    Wow man 19 years. 🙂

  4. Hello Ajith,

    You added all good points. When I was completed my Engineering two years back at that time decided to start a Blogging as a Full Time career (Simply Working from Home). But I am facing problem of Time management because while you are setting in home; You can not care you valuable time.
    Therefore, Working from home is not a easiest task. You need to work hard and make you world. 🙂

  5. If I stop working and start working at home. homework or any home business that fits on the run for the current state it is today?

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