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These Are the Tough Questions You Need to Ask Before Retiring

Gabrielle Olya
Shot of a mature man and his elderly father sitting on the sofa at home and having a chat.

Retiring rich might seem like an elusive goal, but Ted Jenkin — a certified financial planner and co-CEO of oXYGen Financial, a firm dedicated to helping Generations X and Y make good financial choices — is dispensing level-headed, pragmatic financial advice to make that dream a reality.

And his advice has resonated with GOBankingRates readers like you, who voted Jenkin as the Best Money Expert in the Retirement Planning category.

To me, being named the Best Money Expert means being the most trusted voice in personal finance,” he said. “I would like to be the everyday expert that people turn to for financial advice on matters both large and small.”

Jenkin has also been recognized as the No. 4 most influential financial advisor in the U.S. by Investopedia, and is the weekend financial expert on CNN Headline News, a frequent columnist for the Experts section of The Wall Street Journal and serves on the CNBC Financial Advisor Digital Council.

Click to find out how this Best Money Expert planned for his own retirement.

What is your money mantra?

Manage your paycheck better today to recreate a paycheck for tomorrow.

Before achieving financial success, what was your biggest obstacle? How did you overcome it?

My biggest obstacle was getting to my first $100,000 income. It took me two years after college, but I overcame the obstacle by breaking down a formula on what I needed to earn every day versus every year to make it more manageable.

What advice would you give your younger self about money?

Save a third of every pay raise you get so you don’t succumb to lifestyle inflation.

What is the best piece of advice you received along your financial journey?

Pay off your mortgage. The reason it was such good advice isn’t just the pragmatic part of having no mortgage, but really the emotional freedom it gives you when it comes to your overall lifestyle.

What is the best thing you did to boost your retirement savings?

Both my wife and I contributed to an IRA even when we maxed out our 401ks. So many people forget you can do this, which can add another $11,000 to $13,000 a year in additional retirement savings. It seems so simple, yet many people simply don’t do it.

What are some unexpected expenses that can put a retirement plan at risk? How can people better plan for these sudden obstacles?

Healthcare, mortgage expenses, kids, parent care, etc. Most people don’t ask the tough questions they need to because they worry about overstepping ‘financial’ boundaries. Don’t be afraid to ask your parents if they have long-term care or if they have saved money for your kids’ college education and how much in order to allow you to plan better with your own finances. If you refinance your home 10 years before you retire, think about whether or not you can carry this mortgage payment into retirement. By asking both yourself and those that surround you tougher questions today, you can plan better for the sudden obstacles of tomorrow.

Is there a tool or tactic that has been the most valuable to you in your own retirement planning experience?

Using a complete account aggregation tool to create an automated personal financial statement and a key performance indicator dashboard of my personal finances has helped me dramatically with my own retirement planning experience. By having all of my information in one place, I’ve been able to set clear and concise yearly goals and track those on a regular basis. Everyone should use an account aggregation system.

Click to read more from Best Money Experts.

This article originally appeared on GOBankingRates.com: These Are the Tough Questions You Need to Ask Before Retiring