If You Want to Quit Your Job, Get a Plan in Place

I quit my job last month. After 15 years working for a newspaper company – most of it blogging and creating online content – I decided it was time to become my own boss.

Actually I decided almost a year ago. But the timing wasn’t right so I prepared carefully for the day I could make a clean break. In that time, I took several steps to put me in a good position to start a freelance career.

Gave my employer a chance to keep me

Back in September, there was a severance offer to all employees. I almost took it. But my supervisor thought I was a valuable employee and asked me to stay. For that and other reasons, I stayed. Mainly I wanted another chance to be successful in my job.

Made my fiancee my top advisor

She is sharing my life and is part of the choices I make. Her life is affected directly by my decisions. She’s going to have to live with the consequences of my bad decisions and enjoy the benefits of my good ones. That makes her a major investor. So when she expressed doubts and listed the benefits of continued employment. And those benefits covered more than health insurance. She saw opportunities to build upon my name and reputation.

Maximized opportunities at work

I capitalized on those opportunities. I strengthened my commitment to networking around town and in social media. I made more contacts in the business community.

Minimized expenses at home

I also cut my living expenses while drawing a full paycheck. I sold my house and got into more economical housing. This helped me cut debt and start saving. It also lowered the paycheck that I needed to bring home.

Increased revenue at home

The key move was to start freelancing on the side. Yes, the extra money was a help. But a couple writing assignments also taught me a few things about finding clients and making time to work. I didn’t find a lot of work by any stretch of the imagination. It was enough to give me confidence in what I was doing and consider making the jump to full time freelancing.

The payoff

Then in March, my employers offered another severance package. This time I was much better positioned to freelance. I didn’t have enough revenue to live on but I had enough that I could build upon. The severance would make up the rest for awhile. So I went through with it.

My fiance was totally on board this time. During my trial period, we discussed what I was doing and possible plans. She wasn’t surprised by anything and felt as confident as I did about my chances of success. She was ready to support my efforts.

But it hasn’t been a totally smooth transition. I wish I could have been better prepared for my new life.

Should have planned earlier

There isn’t a business plan. I have goals and an outline of what I want to accomplish. But it’s a bit broad. This is important because I believe in concentrating on a niche. And when people – potential clients – ask what I’m doing, they’re more impressed with specific descriptions of what kind of work I do. If they’re in the market for help, they want a specialist not someone who will do anything for money.

But it’s important to realize that at some point you have to just do it. Planning is necessary and helpful. The trick is not to wait until you perfect your plan or you will never start business.

Needed to start marketing materials sooner

I’m still designing business cards. I feel naked without them. Business cards are proof of legitimacy in my circles and I don’t have that yet. To make matters even worse, my website isn’t even finished. I need to put up samples of my work and make it my basecamp for online marketing efforts.

Both things could have been done while I was employed. But it was easy to put such things off because I dedicated spare time to more work and didn’t absolutely need it. I should have made strong goals and dedicated time to building an infrastructure to the business.

Could have built an infrastructure

Part of that infrastructure should have been creating an accounting system. I didn’t need much since I didn’t make much. The withholding from my salary was enough to cover the extra income at tax time.

But I needed the practice tracking that revenue. And I could have learned a lot about what worked for me. I didn’t need to buy an accounting software package or hire a CPA. But just creating spreadsheets with revenue and expenses would have been a great start.

I’m now looking around for a bank to take care of my business account. Again, I wish I had this work done already. It’s another thing that’s taking time away from creating revenue.

And that’s the major issue here. I’m trying to balance building a business with making money. A little more preparation give me more time to actually work. The severance is giving me a great cushion but I would like to be able to save as much as that as possible. Some day it will run out.

Don’t forget you’re still drawing a paycheck

This is the key. I wanted to make sure I kept doing my best for my employers. They still had expectations and paid me to meet them. I owed them that.

Plus it helps keep my reputation in place. Whether I apply for another job or pitch a potential client, they will have no reason to doubt that I give every business their money’s worth.

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Carl Natale is a freelance blogger who writes about tips and advice for small businesses. He runs the site Expensiccino.com - a site about how top brands set their prices.


  1. Johnny on the 15th April

    I just went through a nearly identical experience, after being at a major media (music) company for 8 years (since being an intern) and tried planning my escape for the past year (the exit finally happened this month) to go off on my own. It didn’t go as smoothly as I had hoped — once making the decision to eventually leave I felt that I couldn’t maintain the same amount of enthusiasm for projects at work that I normally would have since my mind was running at high-speed for my own ideas. Especially at a large corporation, the involved politicking, controlled enthusiasm and other intricacies of the day-to-day corporate environment and specialized work are so incompatible with an entrepreneurial mindset — something that you may not pay any mind to when you’re totally committed to your role inside the corp.

    As for the retrospective outlook — all great advice. There is something different about that day after separation, though, that I think cannot be felt while still being committed elsewhere, no matter how much preparation you devote to reaching that day (“hindsight is always 20/20”). And it’s not just the increase in time available for your own endeavors, but the ability to eat, sleep and breathe your own ideas alone. It’s both invigorating and scary at the same time, and no matter how much prep time, you’ll most likely see things in 2 drastically different ways on the day before and the day after that leap.

  2. brandscaping on the 16th April

    Fantastic post Carl,

    I only wish it had been up two days ago – I gave my notice yesterday to make the same leap of faith.

    It’s funny reading this article, because it’s pretty close to the way the past two years have been for me!

    Good luck in your freelancing world, email if you need some moral support!


  3. Jen on the 16th April

    Congratulations Carl! That’s great to hear. I love the practical advice you share here.

  4. Julius on the 16th April

    While creating your plans before quitting your work, I think it’s important to have a timeframe for each task included in the plan. This helps in spending the right amount of time on each step.

  5. Gines on the 16th April

    Excellent timing for an excellent post. At least for me. I am about to embark on a similar journey. You made me think twice to some parts of my plan. Thanks Carl.

  6. Awesome on the 16th April

    A plan is a good thing, I was stupid and quite my first job out of school b/c iI was working 60+ hours a week, eventually I started freelancing and building websites so thankfully everything workout. But in some weird way, NOT having a concrete plan kind of made me work harder since my back was up against the wall.

  7. Carl Natale on the 19th April

    Thanks J. Luckily these kinds of mistakes aren’t fatal. It’s possible to overcome them and still succeed. As we continue we will make mistakes and correct them. Good luck.

    Thank you Jen for the encouragement. And Julius has a great point. I’m including timetables in my plans.

  8. Ryan Cowles on the 23rd April

    I will be having a similar experience sometime soon. Although I might not be my own boss for good, I’m moving, and hoping freelance work can supplement the money saved to help me out.

    Reading this article definitely gave me some things to think about, and I really need to get a timeline and a to-do list together.

  9. Genevieve on the 7th June

    Carl, thank you so much for this post – I found it very encouraging as I’m going through a similar situation at the moment – working hard to get a full-time freelance career going while still at an in-house position Monday to Friday.
    I’ve tried taking the leap before, and while I realised during that period of freelancing, that being my own boss was definitely for me, I wasn’t prepared at all financially, so back into the work-commute I went. I think the experience was good in that it’s taught me to prepare well before going.

    I especially enjoyed the part about building an infrastructure, it’s given me a few more things to get in place while I’m still working in-house 🙂

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