Getting personal here… The past few days have been ones of change, contemplating and second-guessing as things change. Change used to annoy me, but I’m learning to embrace this unavoidable part of life. However, I rarely act impulsively. The ability to think through a decision and all of its implications before acting is one of my biggest strengths as a business owner and employee. It’s saved me from making countless rash, irrational decisions.

One of the biggest decisions I see in a person’s road as they start a business is when to actually make that hard transition from employee to full time business owner. While it may feel good to quit a job in a huff of triumphant emotion, it’s not always the best decision for us. However, working in a toxic environment or stunting your own business’ growth because you’re too emotionally worn upon arriving home isn’t healthy either.

Just because it’s not yet time to quit your day job DOES NOT mean you cannot pursue your passion. A person can get a lot done between the hours of 6PM and Midnight!

1. How many years am I committing to this project?

If this answer is 3-5 years, will taking a break from my job make it more difficult to be hired at the end of my self-employment stint? Will technology change so much that I will be left behind? If you plan to sell your business one day, what are your plans after that?

2. At my core, do I feel like an entrepreneur, or do I have entrepreneurial tendencies?

To borrow a theme from Gary VayNerchuk’s talks, someone who is a lifelong entrepreneur really cannot fathom a world in which they work for someone else. Getting scrappy and making it work as an entrepreneur is the only opportunity and they’re going to try/fail/succeed/try again for the rest of their life. Someone who has entrepreneurial tendencies could survive in either situations, but may thrive being a part of someone else’s business. These are good things to discover about yourself as you handle day to day situations.

3. Do I like letting someone else take the heat?

This question piggybacks off the previous. One major benefit to having a boss is being able to fall back on company wide policies. When it’s just you conducting business, your customers know your decisions are your own. This may lead to temptations to stray from your beliefs, vision and policies due to peer pressure.

4. How stable is my spouse’s financial situation?

Just because your spouse has money now to pay the bills doesn’t mean you are free and clear. What are your long-term goals as a family? Would your spouse like the freedom to search for a new job? Does he or she feel as though he may be fired or let go? Discussing this with your spouse is both considerate and wise, as your spouse feeling stuck in an unfavorable job just to pay bills isn’t ideal.

5. Do I have adequate savings?

What are your savings goals? If quitting your full time job means not being able to save for a house or vacations, is it worth it to you? Perhaps it’s even possible to earn more money by adding a side job rather than quitting one job for another.

6. Do I want to have employees?

If you’re going to build a successful business, scaling in the future should be considered. Being a one man/woman show is only feasible for so long unless you purposely cap your productivity. Do you have the desire/personality/patience/empathy/decisiveness to be a manager?

7. Is further education needed to pursue my goals?

Are you able to make the time and financial commitment to continued education if it’s required to maintain your business? A great alternative to formal education, which can be expensive and time consuming, is to learn by doing in a professional setting. There may be great opportunities available through your current employer to gain additional experience.

8. Do I plan to move soon?

Much of the appeal of small business is that customers can shop locally. Uprooting a business may cause clients to reconsider. If you’re in the service industry, a move can be extremely challenging, since gaining clients is more difficult than keeping them. You may also lose the community you rely on for advice, networking and accountability. On the other hand, moving to a new community gives you the opportunity to meet new people and make more connections.

9. Am I able/willing to handle financial and legal aspects, at least until I make enough to hire a consultant?

These are the not so fun aspects of owning a business. Even so, it necessary and you’ll need to read a lot of technical jargon to maintain a legal and financially stable business. It can be quite a jarring (yet exciting) wakeup call when you realize your hobby isn’t just a hobby anymore!

10. What emotional changes will take place between you and your spouse?

As we know, finances are a common cause of strain in a couple’s relationship. It’s important to discuss this opportunity extensively and often with your spouse. They’re your biggest asset in this endeavour, but only if they’re 100% on board and supporting your decision to quit your day job. It’s also important to discuss how your work hours would change, how weekends you’ll spend away at conferences and meet-ups. For introverts, you should also think about how increased socializing will affect you.

11. Do I plan to have kids soon?

Will having kids change your ability to pursue your entrepreneurial goals? How much will your costs increase? Will they keep you from making money temporarily? Keep in mind that paid maternity leave is becoming more common these days, and this can be a huge lifesaver for new moms.

12. What are my retirement plans?

Planning for retirement is essential! You should make sure this is possible with the amount of income you expect to earn, especially when employer match contributions are eliminated.

There’s SO MUCH to consider.

I hope these questions stirred some thought and give you more confidence to act due to thinking the situation through entirely. Do you have any advice or tips for someone considering this transition? I would love to read about your story in the comments!

Thank You Kindly LLC

P.S. Check back next week as we discuss ways to be your own Personal Assistant in 2017 through use of a kick butt editorial calendar!



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