How to Smoothly Transition from a Desk Job to being an Entrepreneur


Nestled quietly in your cubicle at the corner of the office, you’re currently pondering over spreadsheets and progress reports. You’ve got a few browser tabs open, a couple of which are some of your favorite blogs and Facebook. You are craving the inspiration and guts to just do it...just start up those dreams you have been putting on hold for so long.

Do you walk into your boss’ cabin cold-turkey and give him a piece of your mind as you quit? Or, do you play it cool and decide to weigh your options?

The truth is, there aren’t any easy answers here. To be an entrepreneur, sooner or later you’re going to have to quit your day job to fully focus your time on your business. But, this transition can sometimes be jarring. On the one hand, having a day job means that you have a guaranteed source of income while you are building your business. On the other hand, working 40-50 hours a week makes it very difficult to give your budding business the time and attention that it deserves.

Let’s take a look at how you can move from one world (your day job) to another (your business) seamlessly.

  1. Start small.

Even if you have the greatest business idea since sliced bread, you aren’t going to be able to build it overnight. As a result, there’s no need to quit your job point blank and spend 40-50 hours a week working on something without making sure that it has potential.

Take it easy. Start with an hour a day. If you’re comfortable with waking up earlier than usual, you can spend an hour each morning working on your business before you head off to your job. Alternatively, you can spend an hour in the evening or at night, before you go to bed. Whatever you choose, stick to it.

  1. Always be testing.

Your number one priority in the beginning should be testing your idea to see if it is profitable. Rigorously test each and every aspect of your product or service to see how it works. You need to know what might go wrong and fix things accordingly. You can release a beta version to your audience, or to trusted members of your social network for an outside opinion. It’s easy to get caught up in your own line of thinking. Releasing a prototype to your target audience gives you the opportunity to measure performance in real-time. Learn from the feedback you receive, and always test to see if you can make improvements.

Once you’ve ascertained that you have a sustainable business on hand, you can move on to the next step.

Startup Stock Photos
Startup Stock Photos

Don’t abandon all of your work contacts.

Even if you’re working on your own business, you still have a responsibility to your employer. As long as you are officially on the payroll, you need to show up on time and do your job. This will make sure that you don’t sour any relationships at work that could be useful to you in the future. When the time comes for leaving the company, try to keep things amicable. Some of your colleagues or bosses might turn into clients later.

Before you move forward with your business, seek some legal counsel to ensure that you aren’t violating any non-disclosure agreements or no-compete clauses.


Set realistic, achievable goals.

Your goals are like a loose guideline for where you need to go. Think of it like this, if you didn’t know what your target was, how would you ever know if you hit it?

Any business needs to have short, long and medium term goals. You can decide what each of those time periods mean for you, but at a minimum, try to set yourself daily and weekly targets. When you’re setting goals, make sure they’re challenging, but not impossible. If you set yourself a weekly goal of quadrupling your current user base, for example, that’s not going to work out. Failing to reach goals like this saps you of your energy.

On the other hand, if you set more realistic goals and achieve them on a daily and weekly basis, you will have tapped into one of the most powerful sources of success – momentum. The positive reinforcement you’ve received from completing goals regularly will give you the motivation to push through tough times.

Spend your savings on your business.

One of the advantages of having a day job is that you’ll have a certain amount of money coming in each month. While you’re working on your business, you can postpone any major purchases and invest the money you earn into your business instead. You’ll need capital to build a team, build your website and invest in marketing, among other things.  The best investment you can make is an investment in your business.


Find partners.

Building a new business from the ground up is a grueling, often extremely stressful process. Combine this with the stress and exhaustion that comes with working a 9-to-5 job, and you’ve got a lot on your plate. This is why having a partner for your business is advantageous.

A co-founder can bring a different set of skills to the table. You might be a good marketer and they might be good at coding. Having someone to bounce ideas off, bring new perspectives to the table and share the workload, especially during the early days, is invaluable.  If it just happens to be your spouse, well that is just even better! ;)

Get on a low-information diet.

We’re surrounded by distractions. You can fire up your smartphone, load up Instagram or binge watch Grey's Anatomy on Netflix... and suddenly it’s eight hours later and you have five coffee cups down and donut crumbs all over.

Listen, being an entrepreneur doesn’t mean you suddenly have to develop a Zen mindset and completely become immune to all distractions. On the contrary, as a business owner you need to become aware of your habits and all of the ways in which you usually spend your free time. If that means deleting a few things or canceling some subscriptions, so be it. Use your free time to get inspired and excited by your business.  Stay focused.

Being more productive is often a process of subtraction, not addition.


Outsource wherever possible.

As an entrepreneur who is juggling jobs, time is your most precious resource. You have to leverage your time to achieve the maximum results for your business. As a result, you have to learn how to delegate work. This might mean contracting someone to handle your social media, write content for your blog or develop your app. You could also use a virtual assistant to handle your schedule and manage your emails. Several freelance websites like Upwork and Elance can connect you to talented freelancers around the globe or some amazing Facebook groups with talent bursting at the seems, for example The Savvy Business Owners Group...simply amazing!

It's okay to wait till you’re making money.

At some point, your business will start to make a profit. Oh, the glory!

But, don’t get too excited just yet. Yes, we’ve now established that what you have is a workable business model. But, until your business is making enough money to provide for you by itself, hold off on quitting your job. Reinvest your profits into the business and wait until it grows some more. Soon, you’ll be able to be your own boss, full-time and you will not have so much financial stress.


Make time for family and loved ones AND yourself.

Building a successful business is well and good, but you have to consider the real-world implications of working two jobs. Even when you’re deep in the trenches building your business, take time to spend with your family, friends and loved ones. If you have children, give them your attention whenever you can. Your family understands that things are going to be tough for a while, but you have to maintain a balance between your work and personal life.

Spending time with your family will give you a chance to get out of the office and gain some perspective. When you see the smile on your children’s faces or have a wonderful conversation with your spouse, you’ll realize why you’re doing this in the first place. Connecting with the people you love will give you even more impetus to succeed with your business.

Also allow yourself to relax and disconnect.  For parents sometimes it just might mean a quiet 5 minutes alone or a trip to the grocery store... Whatever it is, carve out little moments for yourself and to fuel your creative fire.

Abandoning the corporate rat-race to jump into the entrepreneurial lifestyle can be tough. We’re not here to tell you that it isn’t. But, if you’re dedicated and strategic, you can use the list above to make the transition as painless as possible.

Here’s to your success!