Image by: dasprid
By Dexter Lunde

Dan Yoo seemed to have it all. I mean, he did create LinkedIn and led their business operations, strategy and analytics teams. This is probably why his choice to move “forward” with a start-up company instead of staying at the prestigious networking company surprised everyone. Why did he choose to make this risky career move?

In an article that he contributed to Entrepreneur.com he talks about how he could no longer move up with the company, his career had plateaued with them. It plateaued at the top, but there was still little room for personal and professional growth for him.

If you’re thinking about possibly leaving your job in order to help with a start-up company or if you’re looking to start your own company, how do you know when to make that jump? Or if you should make that jump? After all, it is a big decision and a risky one at that. If you’re debating on this topic, check out this list to see if you’ve got it in you and if you have what it takes to do what Dan Yoo did.

#1) That Driving Passion

Entrepreneurs and successful businessmen are driven by passion and determination. They may be passionate about what their company is making/offering or they could be passionate about making money. No matter what drives them, it is definitely a deciding factor in whether or not they succeed (when you want something – you’ll do anything to achieve it) and if they are ready to take that leap.

#2) Where Are My Keys?

They’re also organized. Very organized. The most successful businessmen know where everything is because they have to. When you own, run, or share responsibilities of a business, you have to keep track of dates, meetings, numbers, memos, e-mails, conferences, etc. The list goes on and on.

If you’re not organized there are other solutions (like hiring a personal assistant or secretary) but those solutions are expensive. If you’re starting something from scratch, you’ll have to skimp and save money until you start making a hefty profit.

#3) Freelance, Storefront, or Basement?

There are many types of businesses. Some are cheaper to start than others. Freelancers and contractors (for example) don’t have to pay much to get started – depending on what they specialize in. If you want to sell products, you can start with an online store. If you get enough interest and make enough of a profit, you could expand to your own storefront. Some people even work out of their basement.

Once you’ve thought about your passion and what you want to do, consider what you need in order to get it started. Remember that you’re not going to start at the top so you won’t necessarily need to pay for rent of a building just yet. These start-up costs will vary depending on field, market, and availability. Drive-thru coffee stand or Paris-themed café? Freelance web designer working out of you home office or storefront with more than one employee and service?

#4) Can You Afford to Take the Risk?

Some guys aren’t able to do that. They’ve got a family to support and can’t manage the extra risks that come with owning their own business. Mortgages make it hard as well. Single incomes make it even worse.

In my opinion, the best time is when you’re young and don’t have any children yet. You’re married so that you’ve got that extra income just in case something goes south for you – you both can still pay for a roof over your head and afford to put food on the table.

This is why it is important to plan for the emergencies. Have an exit strategy. Talk with your business partners about the warning signs of the business tanking. Remember that your first run may not work. That doesn’t mean that you have to give up. You will need to learn from your mistakes.

#5) Are You a Workaholic?

We often talk about first time business owners not realizing how much work is needed to run their own business. They thought that it would be a cake walk (Surprise! It’s not.). However, people rarely talk about the other side. If you’re a habitual workaholic, you may find that you become absolutely obsessed with working. Your business becomes your life. You may find yourself saying, “But this needs to get done NOW.”

This side of the spectrum isn’t healthy. If you work too hard, you’ll start neglecting your personal life. There will be no room for personal improvement (which is indeed different from professional improvement). Your wife doesn’t like to be neglected. I don’t know her but I can tell you that she doesn’t.

Now it’s your turn. What advice do you have for people who are pondering this endeavor? Are you a business owner? Were there any surprises that you wished someone would have told you about? In what situations should men not jump into the entrepreneurial field?