Home Advice For The Young At Heart Before You Quit Your Job, Do These 5 Things First

Before You Quit Your Job, Do These 5 Things First


by Holly Caplan, author of “Surviving the Dick Clique: A Girl’s Guide to Surviving the Male Dominated Corporate World

How many times have you had drinks with colleagues after a long week and the following situation happens. You sit around a table of Buffalo wings and beer to discuss the latest celebrity debacle, who won the big game, and inevitably, complain about your job. Despite the normal topics of conversation, easily and expectedly, work becomes an anchor in the dialogue. The commonalities of being unappreciated, overlooked and flat tired of office politics are all brewed over. Sound familiar?  Then, as the third round of beer arrives, the conversation, a bit slurred, turns to all of the other things you really want to do with your life and career.

Maybe someone at your table wants to open an online business of sorts, maybe another wants to open her own firm.  Almost everyone has a dream of kicking the 9-5. Wouldn’t it be great to give yourself freedom, creativity, money, and yes, have the life you want? Yet the more you dive into these thoughts, it is the doing it part that can be the hurdle. You may think to yourself, “If I just had time,” or “If I just knew where to start?” and of course, “How do I start my own thing while I’m employed by someone else?” So many of us get caught up in these thoughts because leaving stability of a full-time job can be uncomfortable. Anything outside of what is familiar can feel overwhelming, and so, we stay in miserable and comfortable.  But it doesn’t have to be that way. You can prepare and make steps toward leaving the daily grind, and going off on your own.

Here are five steps for beginning your transition from employee to self-employed:

1. Get Mad!

You have got to get mad at your current situation. Getting mad is your defining moment. Getting mad lets you know that you have absolutely reached your threshold, and there is no looking back, only forward. I had this moment on a July day and didn’t even see it coming. I had just finished a difficult sales call with a customer, walked out of his office into the Dallas 101 degree summer heat, got in my car, and read an undermining text from my boss. I thought, “I’m out. I’m done.” I was pissed, and it was the final straw that propelled me into entrepreneurship. Suddenly everything else was in the rear view mirror.

2. Fire Your Employer.

The best way to start planning your own business is to fire your employer. Set your timeframe by deciding your date of departure from your organization.  Maybe it is 120 days, or a year from now, but either way, you have now empowered yourself and set the wheels into motion. This will give you a feeling of excitement and peace, because you know the day you will sign off of your company computer forever. You will see your future and will push yourself to get your business going.  You are your own boss now, so act like it.

3. Make a 30-Minute Plan.

Since you plan on working for yourself, yet are still committed to the 9-5, do something every day for your new business, even if it is just for 30 minutes. Maybe in the evenings you take 30 minutes to work on your business plan, or begin to create a website. Maybe over the weekend you attend a networking event or apply for your LLC. This way you will know that what you are working towards daily will result in entrepreneurship despite having that full time job. In full disclosure, some days will be better than others. Personal and professional commitments may get in the way of your daily 30-minute plan, but keep the momentum despite life challenges and your will cross your finish line.

4. Set Your Start Date.

Reinforce the entrepreneurial commitment to yourself by setting your start date. This will increase accountability to yourself and rev up your new mindset. You will begin to think on your terms, and not based on someone else’s watch or bank account. Consider the time from which you set your start date to your first day as your practice period. For instance, know that before you open your doors that you want to have 5-10 clients. Take that time to work out your kinks, troubleshoot and get any extra learning.

5. Plug and Play.

You have created your roadmap over the recent months; so now get ready for plug and play on your first day.  Depending on what your business is, have your website ready, your social media pages created, your online calendar set up, and 90 day business plan ready to go. You are ready to tackle your new world and have all of your tools in place, and be ready to go!

Making the transition into entrepreneurship can happen. It will feel exciting and uncomfortable all at the same time. After all, by kicking the 9-5 to the curb you are pushing yourself into doing something different. But different is good. Just work your plan, embrace the change and be proud you are making a difference.


Holly Caplan is a career coach, workplace expert and author of “Surviving the Dick Clique: A Girl’s Guide to Surviving the Male Dominated Corporate WorldCaplan has worked in medical device sales for twenty years. She was a sales rep, sales trainer, and then fought her way into management. Caplan has been featured in top media outlets like Entrepreneur, Cosmo, Cheddar and much more.