Category: Kindness

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365 Coaching Tip: 364th & 365th – A FULL YEAR!

December 30th Coaching Tip: Eat Slow. Eat Less.

Not only do I need to go slow, but now I’m coaching myself on my overall wellness, with a supreme amount of focus and discipline to eat slowly and eat less. No more whoofing down some food quickly. It’s not worth it! Now it’s about eating slowly, taking a break, walking around the home, doing a quick chore, then having another bite of food, then a few steps, etc. There is no need to risk eating fast, nor eating more than a helping. Zero reason; it’s not worth it.

When I say eat less, many of the books on longevity indicate that these seniors stop eating when they get full, or right before they get full. They walk after eating, intentionally. Some even indicate that they eat just 80% of a full meal. I’m implementing eating less; for example, today I had two spoonfuls of tuna salad, with no bread or crackers. Eat slow and eat less.

December 31st Coaching Tip: Celebrate, I Did It!

At the beginning of 2025, I set a goal to blog about a coaching tip every single day of the year. It’s one thing to set a goal, but it’s another thing to be committed to the goal, implement a new habit of thinking about and then writing about a daily coaching tip. I did it, yes, I did it. Did I fall behind a few times throughout the year? Of course I did, of course. But the key is that I was disciplined and committed to the goal and was intentional about taking time to catch up. In fact, today is January 15, 2026, and you’ll notice, I am finishing my last coaching tip of 2025: Celebrate, I did it! Am I a lil late in getting it done? Yes, I am.

It’s my hope that you have enjoyed reading these 365 Coaching Tips as much as I have enjoyed capturing them, writing them down, editing them a lil bit (they definitely need to be edited by a professional editor), and sharing them on this JenWilfong.com blog. How am I celebrating this significant achievement? I ordered myself a gift, that will arrive today via Fed Ex; it’s a gift that I buy myself during key times in my life, times and moments that I truly want to memorialize. For example, one of the gifts was bought when I started received stock options as a leader at Caterpillar back in 1997; another time was when I started my second real estate LLC; and another was when we were returning from an amazing trip and concert in Portugal. Celebrate when YOU accomplish a significant goal. Celebrate that you DID IT!

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365 Coaching Tips: 361st, 362nd & 363rd

December 27th Coaching Tip: Strive For Normalcy.

There’s alot going on with me and my health; there’s alot going on with the holidays and the upcoming new years; and there’s alot going on with geopolitical happenings across the globe. My goal right now is to strive for some normalcy. What does that look like right now? Resting in the hospital, I decided that I might as well finish a couple things online that I had put off in earlier December. I have finished an AI course thru the University of North Florida and completed my continuing education for my PCC Coaching renewal; those both are now posted to my Linked In profile. Why do it now? I’m striving for normalcy, after this shocking and unexpected last week’s health crisis. This mattered, I’m still relevant.

I was also working diligently to get normalcy with my strength (walking and standing regularly), hydration (moving from chewing ice to now able to drink liquids), and nutrition (starting very slowly to eat again, very small portions). The progress to do these three things gave me hope. It will take time, but striving for normalcy is working. It’s good for the mind, heart, mind and soul.

December 28th Coaching Tip: Go Home.

Yesterday at 2pm, striving for normalcy allowed me to slowly eat a small meal of chicken, mashed taters and gravy, and some pudding. Part of me was scared to eat, as I had only had broth for a couple days. I took it slow, one small bit at a time. Immediately upon finishing this first “normal food” meal of three that I would have to eat before being released, I made myself get up out of bed and walked the fourth floor in the hospital. I walked more than all the patients on the entire floor combined; I was striving for normalcy and wanting to prove that I had the strength to go home. Today, after my third, small meal of normal food was consumed, all three doctors agreed with me: it was time to be released and go home to rest, go very slow, and recover.

My partner and I loaded up a cooler with all the flowers that I received, grabbed my personal items, and we headed home. That transition was exhausting, but I was going home.

December 29th Coaching Tip: Go Slow.

It’s a Monday, and what a better way to start the week than coaching myself to go slow, prioritize rest and recovery. I grabbed a black Sharpie marker and made a couple Post-it notes that I put on my bathroom mirror and on the refrigerator, both of them at eye lever. Because this health episode was so severe and scary, I knew I had to write down my priorities so that I would stay acutely aware and focused on them. I also told key people in my life the following: Go Slow. Eat Slow. Eat Less.

Go slow, Jen, go slow.

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365 Coaching Tips: 355th, 356th & 357th

December 21st Coaching Tip: Uneasy? Get Checked Out.

Early Sunday morning and I just didn’t feel right; I actually felt uneasy. I haven’t felt uneasy more than five days in my life. Listen to your body; listen to your gut; follow your instincts; don’t delay. Go get checked out.

I drove myself to a quiet ER and was checked in immediately. Couple hours later I was admitted and had a very serious situation happening. If you’re uneasy, get checked out.

December 22nd Coaching Tip: Have A Health Advocate.

When you are about to undergo some killer testing, make sure you have a health advocate that can speak on your behalf. And when I say killer testing, I do kind of mean it. Today had me facing and enduring lots of x-rays and some contrast/dye injected in me to see where the problems were in my body. As the day progressed from 11:40am to 11:40pm with numerous x-rays, hours upon hours of intense pain and loosing my cookies, there were times when me and my health advocate couldn’t even speak in full sentences. For example, when I needed to throw up, I said, “blue” (the blue barf bag). When I said, “pink”, I indicated that I needed some relief, a quick swipe of a pink sponge on my lips. We made it thru it together, and I’m so grateful that my health advocate and partner was with me in the hospital, hated that she saw me in such strife and horrid conditions. However, she became the best ER nurse during these killer tests.

Who is your go to person when you’re in dire straits, heading to the ER, or in the hospital or going thru some killer pain/testing? If you don’t have a person, get yourself a health advocate. Get it in writing too, as a “Health Care Power of Attorney.”

December 23rd Coaching Tip: Embrace Sisu.

As I was in the hospital, I was beyond exhausted due to excessive vomiting and intense pain, and I was lacking five nights without sleep. However, I was facing a very significant decision for my current and long term health. Thank the Lord that I have been in outstanding physical and mental shape, especially these last 2-3 years as I have focused on being a senior athlete. However, as I faced a big decision with meds in me, lack of sleep, and pain, I knew that I had to dig deeper that I had ever dug recently.

My bestie in Holland, Maleena, reached out to me once she heard from my mother that I was ill and in the hospital. She sent me a couple paragraphs on the word: Sisu. It’s a Finnish concept meaning extraordinary determination, resilience, guts, and perseverance in the face of extreme adversity. It embodies a mindset to keep going when ALL odds are against you, often described as stoic grit, inner strength, action-oriented, tenacity, willpower and overcoming obstacles, and then bouncing back with unyielding resolve.

I embraced Sisu (pronounced “see-soo”) during the evening of Dec. 23, and the early morning hours of Dec. 24th. Although I hadn’t eaten anything and slept very little since Dec. 18, faced extreme exhaustion due to this and the horrid vomiting, I dug deep and embraced Sisu. What did I do? I got out of my hospital bed, still tethered to two separate lines, and walked in place, danced, did squats, moved! This was purposeful, intentional, and wellness coaching of myself. I was all alone, just me and God. It worked; my doctors noticed an improvement in my health situation before noon on Dec. 24th. Sisu! The greatest gift from God on Christmas Eve.

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365 Coaching Tips: 343rd, 344th & 345th

December 9th Coaching Tip: Talk It Out, Talk It Out.

As I was in my office today, someone knocked on my door and needed to “talk.” Thank goodness I had a free slot in my calendar for about 45 minutes. Talk she did, and talk, and talk. All I did was listen for the entire time, and then at the end, I asked her: what are your options. She believed that she had two options and then settled on one on the options. Sometimes, people just need someone to talk to; know when you need to just listen. Know when to not even ask questions. Know when not to provide advice. Just let them talk it out.

December 10th Coaching Tip: Don’t Blow It All.

For centuries, people have spent decades building their own personal brand, based upon the daily decisions that they make. It takes discipline to stay on the ‘straight and narrow’. It’s so easy to deviate and slip.

Today, a story was released in Michigan about the head football coach having an extra marital affair; both parties are at fault. Many know that. With the holidays approaching, I can’t imagine on this head coach’s wife and three kids feel about being betrayed.

This lack of discipline causes so much harm; those impacted are too many to mention. With your daily and weekly decisions, take 10-15 seconds and pause, think about your consequences, before you take a significant action. Don’t blow it all.

December 11th Coaching Tip: Empower Someone.

Earlier this week I was asked to travel from FL to TX for a couple days of meetings in mid-January. The leader really wanted me to be there, however I was hesitant to commit, since I’m already traveling in three of the four weeks in January. What do I do here?

I reached out to my colleague in TX, and asked him if he was going to already be in that area during mid-January. Good news, he was. Empowering him, I asked him if he would like to go to the team’s offsite (instead of me). He said yeah, for sure. Then he asked for time to get him up to speed on the work ahead. I will gladly help prep him, and he’ll deliver with excellence. Empower people!

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365 Coaching Tips: 340th, 341st & 342nd

December 6th Coaching Tip: Big Ten Champs; It’s Not A Dream.

Two years ago, the Indiana University football team had more losses in Div. 1 football than any other program. Kinda the worst, right? Fast forward two years later, and IU football is the top ranked team in the country, the 1-seed in the College Football Playoffs, the only undefeated team remaining in all of Div. 1 college football, and the Big Ten Champions,

IU upset the Ohio State Buckeyes, although both teams were undefeated and Ohio State was a 4.5 point favorite. IU’s team scored just enough points, 13, to beat OSU by 3, as they only scored 10 points. The defense on both sides was playing; both field goal kickers missed short kicks that they had hit all season; but the quarterback for IU was just simply better. He was able to march the offense down the field with pinpoint passes when necessary.

This new coach, Curt Cignetti, has instilled “unshakeable belief” with this team and his entire IU organization. The leadership at IU is supportive, too. Belief. Having belief can bring you Big Ten Championship feelings, and it’s not a dream. It really happend.

December 7th Coaching Tip: Tell The Truth.

Received a phone call today from a friend who wanted to share a difficult situation that he got himself into and was responsible for. To his credit, he reached out to me to let me know. I listened, asked a few questions, but mostly let him talk. At the end of the call, I thanked him for entrusting me and telling me what was going on. Then, I shared a story with him about some bad times that hit my grandfather when he was a young father and in his 30’s. Then I gave him one piece of advice: write a letter or go visit them face to face and tell the truth.

Today’s tip is to write a letter to who you impacted negatively. Apologize and offer to repay the remorse; ask for forgiveness. If you can, talk to them face to face. Let them know you care, that you’re human, and you’re asking for forgiveness and empathy. Telling the truth goes a long way, in writing or face to face, or both. Tell the truth.

December 8th Coaching Tip: Rose Bowl Bound.

With the Indiana University football team winning the Big Ten Championship a couple evenings ago, we are now in full-planning mode to watch them as the #1 seed in the College Football Playoffs (CFP) play on New Year’s Day 2026.

Tickets to the game are driving up anxiety levels with some of my friends who are also going. Airlines are maximizing and charging hefty prices. Hotels are piling on, too. But, it will be worth it. For me and my friends, this is about goals, wellness, and being purposeful. It’s a bucket list kinda trip to see YOUR team play on New Year’s Day in the Rose Bowl game. I love roses, but I’m not going for the parade. I’m going to see IU win the Rose Bowl, so that we can then be Peach Bowl (Atlanta, GA) bound.

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365 Coaching Tips: 337th, 338th & 339th

December 3rd Coaching Tip: Salmon Go Upstream.

During one of my coaching sessions today, a team wanted to find capacity by reducing the amount of smaller clients. Why? The team was becoming bored and getting stuck in doing service, and yet the team wanted to grow and handle more complex clients who truly needed financial advice in helping solve their problems.

We took some time to go thru each and every client; the team color coded them green, yellow, red, or salmon. Green was for great client, complex, enjoyable. Yellow was a potential for someone else to care for that client. Red was a definite, better served by another team. Salmon, on the otherhand, was the color for clients who had more opportunity to be served more thoroughly by the team. For example, they had complexities in their business or financial life, they were about to sell their business and needed trusted advisors, they were setting up a family foundation, etc. The color of salmon was selected to reinforce to the team that the team should swim upstream with these clients; it’s hard work, but highly gratifying. We will check back in on their results in a few months. The goal is reduce their clients by 40%, so that they have more time to serve the complex needs of their preferred clients, those who are green and “salmon.” Be curious and have the courage to build the business that you want to run; be purposeful and resilient in saying yes…or no.

December 4th Coaching Tip: Quick Bursts Of Work.

We pulled into the garage this evening around 7pm after a full day of work, then dinner out before seeing my first NCAA volleyball match (IU beat Toledo). The super moon was providing some extra light that reflected off of the snow on the ground. Wanted to marvel at the moon for a bit. I choose NOT to go inside and sit down. Instead, I put on my boots and gloves, and walked the yard, picking up branches and sticks that had come down with some recent blustery winds. Then I removed the decorative pumpkins and also put the metal firepit inside the shed for the winter. Checked the location of my security camera to ensure it’s working and it was. Yes, it’s cold outside, but I was able to leverage the light of the incredible full moon and get in a quick burst of work that I knew could be done before relaxing the rest of the evening.

December 5th Coaching Tip: Embrace AI to Stay Relevant.

The opportunity arose today to work with three of my colleagues on how we all are utilizing AI and Copilot in our jobs. Over the past 2-3 weeks, I was able to collect multiple examples that were significant time savers, allowing the people/teams to be more efficient and more intellectual. One example was quite jaw dropping, i.e. heading to a huge meeting, the leader asked for one-page summaries on the 10 leaders/board of directors who would be sitting around the table. Copilot was prompted to give a one page summary for each of the 10 leaders, giving a multitude of info that was helpful in the wealth management space when a client is selling a business.

Since I was introduced to Copilot just over two months ago at work, my coaching work has been transformed. I’m able to quickly summarize my coaching notes, with more effective action plans. If I’m asked for advice or for some consulting, I ask Copilot for a response to help pull more intell to me. Bottom line: embrace AI to help you in life and your work life. If you don’t embrace it, you may become somewhat irrelevant. The skill in the future is to be able to master your own skills and strengths, while leveraging AI to be more efficient.

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365 Coaching Tips: 334th, 335th & 336th

November 30th Coaching Tip: Step Up, and Say YES.

The Indiana women’s basketball team was 7-0, and now facing 10th ranked Iowa State today. Bad news hit the IU team, as our 2nd leading scorer and rebounder had a lower leg injury and unable to play in this important game. Another player stepped up (let’s call her #8) and started the game. She was up against one of the top five players in the country, Iowa State’s Audi Crooks. IU’s #8 was asked to step up, and she said YES.

Did IU win? No. Did #8 stop the Crooks? No, in fact Crooks scored 47 points, setting an ISU school record. Did IU compete closely til the last few minutes of the game? Yes. Did #8 make us all proud? Yes. When you are ever asked to step up, have the courage to give one answer: YES!

December 1st Coaching Tip: My 2025 Word is REDUCE.

I’m pleased with my selection of my word of the year: Reduce. Back in late 2024, I wanted to reduce plastic usage, my weight, any work drama, and my times in my training. It worked. My kitchens now have much less plastic in them; I eat on non-plastic plates and bowls, I have zero non-stick pans now, and I have new kitchen cooking utensils. My weight reached my lowest level since 10 years ago (my college playing weight). Although we have had eight work colleagues retire/resign from our team, I keep working away and providing value to my coaching clients. And with my training, I see three personal bests in my 100m, 200m, and 400m runs, but reducing my times in all three events. Reduce worked.

So how do I keep it going for the remainder of 2025? I decided to reduce my social media usage in December. How did I do this? I moved all of my regularly used social media apps (Twitter, Instagram, Facebook, TikTok) to my last page of all of my apps. I had zero desire today in my first day to look at these apps, which formally consumed way too many minutes per day. The 2nd thing that I did was start listening to an Audible book on AI, plus I put two print books by my evening chair. Third, I put in a reminder in my iPhone calendar at 7am every single morning in December that reminds me: reduce to zero social media app usage.

December 2nd Coaching Tip: Bring In The Experts.

One of the best and fastest growing teams that I coach brought in the expert today. They needed to spend a full day together reviewing processes, which ones need attention, which ones are running smoothly. They also asked the expert to show them all some shortcuts on how to implement all the digital tools already in their hands to gain capacity.

Because the expert was brought in, everyone on the team showed up, paid attention, asked questions, and learned so much about what is now capable for the team to execute. When there is doubt and a team is pushing back on changing, recommend that you bring in the experts to calmly show what is available and can be done, and how others are utilizing it.

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365 Coaching Tips: 331st, 332nd & 333rd

November 27th Coaching Tip: Just 4:48.

Once again, I traveled on Thanksgiving morning. When I used to live in Houston, TX in the late 1990’s, I would fly from Houston to Indianapolis, rent a car, and drive to Mom and Dad’s home in Kentland, IN. I was able to arrive before my own family who lived in Indiana. Fast forward to today, I left at 6am from my door in Indiana. Took an Uber ride to the IND airport. Two-hour flight to RSW in Ft. Myers, FL. Got picked up by my driver, Ben. He dropped me off at 10:48am at my home in Naples, FL. Door to door on Thanksgiving morning took just 4:48. Four hours and 48 minutes on a holiday. Grateful for all the people that chose to work and assist all of us who are traveling. The kindness was everywhere; everyone was saying “happy Thanksgiving” and smiling, helpful, and nice, even though we were all working to get somewhere. Let’s keep that kindness going.

November 28th Coaching Tip: Cook At Home.

It’s Friday night and one of my best friends is coming to hang out for the weekend. We texted quickly and decided to cook at home this evening. With all the hustle and over-eating that surrounds Thanksgiving, it was the right decision.

At 8:30am this day after Thanksgiving, I headed to Aldi’s (only three other people in the store…it was lovely) and bought some groceries for dinner and for the next couple weeks, too. Here’s the menu for our Friday dinner at home: scallops seared in butter and garlic, fettuccini tossed in alfredo sauce, topped with salt, pepper, and parmesan cheese. Fresh salad with spinach, scallions, tomatoes and balsalmic dressing. For dessert, we made a strawberry cherry jello salad with whipped cream. No alcohol, just water. (The Aldi grocery prices allow you to afford an AMAZING dinner that’s healthy, in the comforts of your own home…try ALDI’s if you haven’t already).

Not sure how much this dinner would have cost us had we gone out, but probably $35-$50 per person. Instead, we ate at home, had a great conversation as we both cooked in the kitchen, and took our sweet time eating. We even delayed our dessert for over an hour. It was a yummy evening; cook at home.

November 29th Coaching Tip: Go See The Sunset.

It was a nice, slow, and relaxing Saturday in our south FL home. It was closing in on 3pm and my friend and I both were still un-showered and in our PJ’s. Finally, we looked at one another and said, let’s take a drive to the beach, grab a drink, and see the sunset. We quickly got cleaned up and jumped in the car and headed to the Gulf. We leveraged Ai and it confirmed, sunset was at 5:34pm E. Our goal was to be seated at the Ritz Carlton in Naples and having a drink and appetizer by 4:30pm E…or we wouldn’t have a seat. We made it, perfectly timed, and enjoyed the sunset. I got a few photos of my friend, and he quickly loaded those up as new profile photos. Don’t miss an opportunity to see the sunset. Sunsets have the “IT” factor; hard to explain, but they just have “IT”.

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365 Coaching Tips: 328th, 329th & 330th

November 24th Coaching Tip: Time With The Younger Generation.

These three posts will bounce and weave around each other. Ask yourself the questions: are you spending time with the younger generation(s)? Are you staying in-touch and relevant? Are you listening to their concerns, hopes, and dreams? Are you willing to assist them? Or, are you out of touch and complaining about them and their desires?

Today, my uncle and I spent the entire day together. We left my mother’s home, and decided to drive a couple hours to our newly remodeled home since he wanted to see it. By the way, he absolutely loved it. We ended up staying overnight there, after we drove around the campus at IU, and had some dinner and ice cream. He enjoyed spending time with me and seeing how I did the remodel. I enjoyed hearing more stories about his times at IU and what he’s working on currently.

November 25th Coaching Tip: Time With The Older Generation.

My uncle and I took it easy today, before we headed to the airport for his trip back to Colorado. We drank some coffee, talked, and then walked down to my basketball barn and got some shots up for about half an hour. As we were shooting, he reminded me to make sure that I’m out there shooting at 80+ years old…like he was doing today. It was a good reminder to me, from him, to keep going, keep moving, keep shooting baskets. I learn so much from hanging out with the older generation. Spend time with them.

November 26th Coaching Tip: Mentoring Goes Both Ways.

Kids can teach you alot, if you just ask them questions and remain curious. I got to talk to two of my great nieces and nephews over the weekend. I can tell that my great niece is a leader of others, and her style and way with communication helps her be effective. I can tell that my great nephew loves being competitive and around top talent in sports. He loves sports, his PE class, and his buddies.

Mentoring can and should go both ways; older generations have alot to learn from the younger generations (from technology to style to new trends) and the younger generations have alot of wisdom that they can gain from the older generations. Both generations have to be willing to care, listen, ask questions, and be grateful for the insights that are being shared. Mentoring should go both ways, not just one way, from older to younger.

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365 Coaching Tips: 325th, 326th & 327th

November 21st Coaching Tip: Baking Up Traditions.

For decades, I’ve been baking bread, pumpkin bread and pie for Thanksgiving. It’s just what I do. One of my nephews loves my pumpkin bread, so I double up the recipe to make him a couple extra loaves; I give a couple loaves to my mom (she adds her cheeseball on top of the pumpkin bread) and of course, I make me some extra muffins as well.

Our family over the last few years just isn’t eating as much as we have in the past, so I have had more leftovers of my baking goods than previous years. As we celebrate in the future, making a single batch will probably be just fine. But I don’t want to stop baking; I love baking at Thanksgiving. It’s a pleasure to make goodies for my people, deliver it, and share the yummy-ness. I love traditions and until I die, I’ll keep baking pumpkin bread.

November 22nd Coaching Tip: Don’t Miss Celebrations Of Life.

As mom and I are prepping for our early Thanksgiving dinner, I let her know that I would need to leave in the middle of the day to go attend a celebration of life for my friend of nearly 20 years, Mike. My mom and dad were great examples of showing up: they made the decision to attend funerals to share their respects, meet with the family, and share stories. Showing up is a challenge at times of grief; sometimes it is exhausting to make the effort to go share your respect. However, I choose to think of it this way: whatever I’m feeling about this loss, the family is most likely feeling it all at a much deeper level. So just go to funerals, or send that sympathy note/card, or make a contribution in their honor to a charity of their choice, or call them a few weeks after the funeral/celebration of life is done and gone. Bottom line, don’t miss them.

November 23rd Coaching Tip: Early Thanksgiving.

Again this year, we as a family had to be flexible and make a Thanksgiving dinner work for nearly all of the family members to attend at my mom’s home in NW Indiana. We landed on the Sunday prior to Thanksgiving this year; last year it was the Sunday after Thanksgiving. My mother loves Thanksgiving and decorated her home so beautifully. She has a tradition of many of us sitting at her long, Amish-made cherry wood table, saying the Lord’s prayer together as we hold hands, and then topping it off by each of us sharing our thankfulness. It brings us to tears. This year, mom reminded everyone of how her grandmother (Kate) came here from Lithuania, from Antwerp to Ellis Island, after her boyfriend (William) had come three years earlier, worked, saved enough money to get her on her voyage to the USA. This message by my mom was so thoughtful, especially during these times of immigration crisis’s all over the world due to instability in the daily lives of many. Our early Thanksgiving was a beautiful gathering of our family and homemade food. We make it work, even though not everyone was able to attend.