The Key Ingredient You Need to be Successful at Work! (and Life)

Ugh, I hate that I wrote that title. I. AM. NOT. A. LIFE. COACH!

I don’t write about sports as much as I used to. When my sons were in sports, and I was coaching, I bet I wrote some sort of sports analogy about once per week. The thing with this idea is it works in sports, but it really works in almost anything in life.

Okay, here it is:

“Having people around you who want you to win is key to success.”

I’m not going to take credit for this, nor will I give credit to anyone because I have heard something like this for the last twenty years, but I find almost always people forget about this one simple but powerful idea.

We discount how much of our success is tied to being surrounded by people who want us to be successful! Or we give ourselves too much credit for our own success. We think we’re smarter or better when in reality, we are all about the same, but the circumstances we find ourselves in are very different!

I tend to find myself in conversations with parents regarding their high school and college athletes who are working on going to the next level because I’ve had kids and a wife who played sports at a high level. What most parents and kids don’t understand is how important it is to play for a coach who truly wants to see you succeed. Wait!? Don’t all coaches want to see every player they have on the team succeed? Nope. Unfortunately.

In college athletics, when coaches change, they inherit a bunch of kids who they didn’t recruit, so they aren’t fully invested in these kids. While they will need some or most of these kids, in the short term, to be successful, Almost always, they will bring in their own kids and be more invested in them.

We are currently seeing massive transfers in all sports taking place in college athletics, and a large part of that is kids trying to find a coach(s) who truly wants to see them succeed!

It sounds like when leadership changes take place at work, right?!

When a new leader comes into your company or work team, we see the same type of behavior. New leaders want to bring in their own people. Why? Because you need to surround yourself, even as a leader, with people who want to see you win! Individual contributors need this. Leaders need this. Anyone who wants to win needs people around them who want to see them win!

It’s not about just making it. Keeping it going. It’s about seeing you win. That’s key. Don’t think you can exchange that for something less.

This is why it’s key for you to put yourself in a position where you feel everyone around you wants to see you win. If you’re a leader and you have people on your team that you are unsure they want to see you win, you need to get rid of those people. If you are in a job where you have a leader or peers who don’t want you to win, you need to find a new job immediately!

See, this is why I would be a shitty life coach. I never want people to leave their job. It’s not in my DNA. Keep that job. Make it work! Then I write this post and say leave your job immediately if you are not surrounded by people who want to see you win!

I have some very close friends in my life. The one trait I feel for each of them, without an ounce of jealousy, is I want to see them win! My own team at HRU, without a doubt, I want to see each person I work with be massively successful and win all the time! Surround yourself with people who want to see you win!

Timmy Sackett, World’s Worse Life Coach, Out.

Don’t Offer Yourself Up to the Burden.

I was on TikTok the other night. TikTok for me has become my mindless tv. You know when you’ve had your normal busy day and you just want mindless interaction before you go to bed. The TikTok algorithm is amazing. I get all my golf vids, funny vids, political vids, puppy vids, and out of nowhere last night the algo snuck in Conor Crippen.

I was now all in down the Conor Crippen rabbit hole. I don’t even know why the algo surfaced this up, but damn it, I love it! it’s an inspiring story and I’m laying there watching Conor videos and I’m laughing and crying and smiling and if anyone saw me they would have thought I was probably having a breakdown of some sort!

Here’s Conor’s story:

On Conor’s site, he has this saying and it won’t get out of my brain: “Don’t offer yourself up to the burden.” He goes on:

“Every day, no matter what you are going through, you have a choice. You can either give in to the burden you’re facing or refuse to let it define you.”

I needed to hear that. Almost everyone I know needs to hear that.

Conor’s story is inspiring not just because of this perseverance and strength, but also because of his mother’s perseverance and strength! His aunt wrote their story in the book titled, “Just Give Me the Road” based on a quote his mother said just hours after his accident. It’s an amazing story.

Make sure you follow Conor on TikTok:

https://www.tiktok.com/@crippenconor/video/7081670691757575466?is_from_webapp=1&sender_device=pc&web_id=7094594753518913067
@crippenconor on the TikToks

You can also hire Conor to come to speak at your event! I hope that I get to meet Conor at an event I’m speaking at in the near future!

Also, shoutout to TIkTok for taking my mindless activity time and helping me find such an amazing person!

Who is in your circle of Care?

I was on the Workday Ventures analyst call yesterday and they had one of their new venture partner companies, Wellthy, and their CEO, Lindsay Jurist-Rosner, on to discuss her company and experience, etc.

Wellthy is a fascinating company, especially when you take into context the current demographics of the U.S., and really all industrialized countries. Wellthy is a digital care concierge service. Think about taking care of aging parents and how you have to deal with the logistics and administrative burden on top of everything else. This is where Wellthy steps in and helps families with this burden.

Lindsay said something profound that stuck with me in terms of how they look at each family and their ability to care for their family: “Who is in your circle of care?” Meaning, when you need help, who are those who will take care of you. What her company finds is it’s almost always the parents. For so many people, this is problematic and that problem is growing as we live longer and a larger portion of the population ages.

It’s not just helping to take care of aging parents, although that is a giant issue, it’s also how we care for our own children, or extended family with needs, maybe even a close friend or neighbor who relies on us (their circle of care).

I’ve written before about how helpful my personal board of directors has been to me over my career with big decisions. I never thought about my circle of care!

Can you write down your circle of care network?

Immediately I have my wife. She’s the CEO of the Timmy circle of care network. I would also put in my Dad, even though he’s about to turn 80, if something happened to me, he would do whatever he could to care for me. My three sons would also be in there, but honestly, until this moment, I never even thought of them in that context. But they are adults and if something happened I know they would gladly find me a home! (just kidding – they wouldn’t be happy about the price and money being taken out of the estate!)

Beyond family, I have my co-workers that probably know more about my medical issues than most of my family. I mean we spend so much time together, so I’m guessing they would also be considered part of that circle of care. I have some neighbors and friends that would help out in a pinch from time to time, as I would do that for them as well.

As I write all of this down, god damn, I’m a pretty lucky person. I can count on a lot of people in my circle of care.

Unfortunately, most of our employees aren’t so lucky. Many have almost no one that they could count on within their circle of care. This is why Wellthy and this type of technology are growing quickly within the HR Tech landscape. We no longer live in a world where we can expect to keep their personal lives at home and not have it impact their work life. So, the best companies will find ways to support an employee’s circle of care.

It’s interesting if you think about it, at every age we need care and support. Some of us are lucky to have that robust circle of care along the way, but many will never have it, or have it and lose it, or not have it and gain it. All of our employees will be at different levels of support, no matter their age, gender, ethnicity, etc. As health care issues are taking a national stage currently, it’s important for us as leaders to rethink how we are supporting our employees and their wellbeing.

What is the Health Insurance Design Impact to Employer Paid Abortions?

Obviously, we had major news recently around abortion rights in America.

What I really want to talk about today is an amazingly quick response by organizations to immediately offer a new health benefit. Within hours of the announcement, we saw major employers come out publicly stating they would pay for the expense of their employees to obtain legal abortions if they could not get one in the state they lived and worked. Some employers also announced that they would pay for relocations for their employees to live in states with legal abortions.

All of this, just from a health benefit plan design perspective is quite remarkable!

Most employers can’t agree on offering smoking cessation programs for their employees or paying for gym memberships, but within hours, we are now paying for abortions. We have severely unhealthy obese employees, but we won’t pay for bariatric surgery. Organizations tend to move very slowly in making benefit design changes, and those changes tend to mostly be around cost/benefit.

Are we being “Inclusive” by offering an abortion benefit?

Again – I’m 100% in favor of a woman’s right to choose!

But we need to have a conversation about the hypocrisy of some of these decisions being made around this issue. This is what we do as professionals in HR. We discuss decisions we make as organizations, and how each decision tends to lead to other issues we can’t yet know what they might be.

So, we are now offering abortions as a health benefit. Why?

Let’s say we are willing to pay $5,000 dollars for our female employees to get an abortion. It definitely makes us sound like we are a very progressive employer! It’s interesting, though, that many of the employers who are willing to pay for your abortion are not willing to pay for your parental leave if you chose to keep your baby. They are unwilling to pay for childcare assistance after you have your baby.

Why is that?

Could it be, that not having children make you a more productive and less expensive to insure employee?

We must ask ourselves this question, if not only to ensure we are being inclusive in our insurance offerings to our female employees.

If you want to be “inclusive” you offer a woman a full choice. Yes, you can choose to have an abortion and we’ll support you! Yes, you can have the baby, and we will still support you! If you only choose one side, you are being exclusionary. Why?

Abortion as an employer-paid health benefit

There are benefits we pay as employers that have very little financial impact but make us look like we are an employer of choice. College Tuition reimbursement was always the biggest one. We offer you college tuition reimbursement knowing almost no one actually takes advantage of it. It’s one of the lowest-used benefits a company can offer! But, we feel great about ourselves when we market this out to candidates and employees.

Are abortion benefits the next college tuition benefit? You offer it up, knowing it makes you look like a progressive employer, but you know it really has very little financial impact. On the flip side, offering paid parental leave and childcare assistance, well, those benefits actually cost us real money, so no, we won’t offer those!

All women should be allowed to make their own choice with their bodies. Period. Employers are going to decide if they should help women with that decision. I think we, as HR leaders and professionals, should be advising our executives that having a “Choice” is about more than one option. Our benefit plans should support any choice a woman wants to make, not just one.

Abortion is health care. Having and caring for a child is health care. Organizations need to support all choices that a woman might want to make.

Being Fully Authentic Is The Worst Advice You Can Give Someone!

I went to the SHRM Annual Conference this past week. I bet there had to be six different sessions, all jammed packed, with speakers telling HR Pros to “Become their Authentic Selves”. Just typing that makes me throw up in my mouth a little.

I call this content, HR Lady Candy. You might think that is sexist but it’s just data. 80%+ of the SHRM audience is female. Those of us that speak at SHRM are building content for women. Viewing the packed rooms, HR Lady Candy sells and it sells well!

But, it’s awful advice!

If you are truly authentic and bring your whole self to work, you are bringing all of you and I’m just going to take an educated guess that there are parts of you better off left at home. Parts of you that you yourself aren’t extremely proud of at certain times. Yes, these parts are part of you, but just as I don’t walk around outside my house naked, there are certain things I don’t need others to see.

I don’t judge these speakers and their full rooms. It’s so good damn empowering to feel like you aren’t true to yourself and have someone on stage in a power position telling you to “just do it!” It’s freeing. You want to run out of that room and just let your freak flag fly! But usually, in reality, that freak flag isn’t the freeing and empowering tool you hoped it would be.

The vast majority of us in the world, need a good-paying job with good benefits. The vast majority of us want to work hard and get promoted. We want to be the best version of ourselves as much as we can. We want to be wanted by others and grow our relationships with like-minded people. “Like-minded” means how we think like most of the time. Not how we think in our worst and most vulnerable moments. No one wants to be judged in those moments. Yes, that is part of our true self, but it’s not the true self I want others to see.

But, that content isn’t very sexy. No one wants to go sit and watch a speaker say, “Just be more normal!” it’ll work out, on average, a ton better for your career!

Freak flag flyers are awesome. We celebrate them. It usually works out for about 1 out of 1,000. Are you willing to bet your career on a .01% chance of success? What if I said the freaks are successful 1 out of 5! Oh, 20% of the time they are successful. Will you stake your career on that? Doubtful, that’s still really risky!

We love to believe the SHRM HR Lady audience is super conservative. That tends to be the profile of HR professionals. This just might be why we are so attracted to the “live your true self” content. We like it because we know we’ll never really do it, but it feels so good to dream!

The Big Regret! How’s that new job treating you?

When 4-5 million people per month change jobs, mostly for more money, there are going to be some consequences! Turns out, the grass isn’t always greener when you get more green!

A Muse survey, reported in the WSJ, recently found out that nearly 75% of workers who’ve changed jobs recently have regretted it, and 50% of those would try and get their old job back! That’s a lot! But it’s not surprising.

The biggest stressors we have in life are having kids, buying a house, and changing jobs. We tend to make bad decisions when stressed, and when you have 4-5 million people per month making that decision, well, that’s a lot of bad decisions!

What will we learn from the Big Regret?!

1. Money isn’t everything, but once you get more of it, it’s hard to go back to the old money level.

2. The old job and the old boss didn’t really suck, and the stuff we thought sucked at the old job, suck at the new job as well. It’s called “work” for a reason.

3. The power of someone paying attention to us and making us feel pretty is the most powerful force on the planet. Never underestimate it.

4. You can go back to your old job, but it will be different. It’s like going back to your ex. You are both a bit smarter and a bit more cautious now. There are some scars. Same people, same company, same job, but it’s not the same. Doesn’t make it bad, but you can’t expect it to be the same.

5. You can’t really judge a job until a couple of things happen: 1. You actually know how to do the job fully; 2. Co-workers stop seeing you as the newbie. In every case, that timeline is different. Be patient and do the job before you judge it.

6. If you find that you have an asshole boss at every job you work, the asshole might be you, not the boss.

7. In the future, when we have more jobs than available workers, let’s not act surprised when people start changing jobs. It’s happened in every similar economic cycle in the modern world. It’s called oppotunity. Don’t confuse that with the world has changed.

What should you do if you hate your new Great Resignation Job?

  • Take some time to really determine what you hate. Was that different from the old job? Was it the same? Will it be that way at the next job? Too many folks don’t know what they hate and they just keep selecting the same jobs they hate time and time again, but with a new pay rate and new address.
  • Some of us immediately want to return back to our old job. That might work, it might not. A psychological thing happens to so many managers once you leave them. It’s like you broke up with them and now you want to run back to that comfort. You’ll find many have no interest, and it has nothing to do with your value and performance, and everything to do with them feeling like you’ll hurt them again.
  • Try and find something you like to do, but call it “work”. This is different than the B.S. you’re told about work doing something you love and you’ll never work another day in your life! I’m no life coach, but that crap doesn’t work. You call it “work” even if you love it, because one day you’ll show up to do what you thought you loved and find out its work, and you’ll be depressed and broken. You don’t love work. You love your family and your God and puppies. You work to put yourself in a position to be able to do what you love. If you’re super lucky, every once in a while those two things will overlap.

Digital Transformation of Work & Wellbeing – @SHRMLabs Report

I got invited recently to be a part of a think tank of sorts on a project with SHRM Labs and Techstars Workforce Development Accelerator discussing what technologies are needed to help navigate the new digital world of work. What the heck does that mean? Good question!

If you haven’t checked out SHRM Labs they are doing some amazing work around innovation, technology, and work. Led by Guillermo Corea, SHRM is working to take a leading stance on the technology that is built for HR. This isn’t your grandmother’s SHRM! Shout out to Hadeel El-Tashi, she has been amazing as well on the SHRM Labs team.

Basically, we have three types of worker environments right now:

  • Full On-Premise work
  • Hybrid
  • Full Remote

Full on-premise work we’ve been trying to build tech and processes around wellbeing for a long time. To limited success, for sure, but still, it’s been a long focus for technologists and HR for decades. Hybrid and Full Remote, while not new, were limited in use, so the focus was not there, then the pandemic thing happened and this had to ramp up really fast.

What we found is there are limited options for organizations to truly and robustly support their team’s well-being when they work remotely and in hybrid scenarios. Here’s the basis of the report:

This report highlights participants’ voices on each of these points. It proposes ways to foster work/life integration in remote- and hybrid work environments, followed by an exploration of elements that constitute a great employee experience and effective employee culture, closing with a discussion of how companies can attract (and retain) the best talent in the face of a tight labor market and the Great Resignation.

You can download the report here

What were our main findings:

  1. All organizations need to find ways to embrace flexibility in the workplace. Not just white-collar workers, but all workers. Flexibility and “All” is a difficult undertaking.
  2. Give employees agency and develop accountability. I call this one, treating employees like adults, but smarter people in the think tank had better words than me!
  3. Drive efficiency and asynchronous communication tools. Stop the non-stop stream of zoom meetings thinking that’s how you’ll communicate effectively with hybrid and remote workers.
  4. Personalize benefits and improve the employee experience. We still deliver benefits mostly like it’s 1970. Everyone gets a 401K match, even if that’s not your priority and you have student loans or want to buy your first house. Or we offer student loan repayment, but you graduated thirty years ago and paid off your loans, twenty-five years ago. One size fits most, is a crappy experience.

We also had findings around building digital culture and attracting more workers – you can download the report to check those out.

Overall, we’ve got work to do in HR as a total function, including TA, Talent Management, Learning, Benefits and Compensation, etc. This is invigorating for the field and there are so many passionate technologists in our space trying to help us develop great solutions for our issues.

I’ve been studying the technology in our space for the past decade and I’m always amazed that the process of what we need and what’s available is ever-evolving. The pandemic while awful, has opened up the world of work in ways we’ve been pushing to make happen for decades with little movement, then this tipping point happened and it’s like HR is being reinvented all over again.

It’s an amazing time to be in our profession!

Do you want to find more happiness at work? Here’s how!

In 1942 Viktor Frankl, a prominent Jewish psychiatrist, was taken to a Nazi concentration camp with his wife and parents. Three years later, when his camp was liberated, his pregnant wife and parents had already been killed by the Nazis. He survived and in 1946 went on to write the book, “Man’s Search For Meaning“. In this great book, Frankl writes:

“It is the very pursuit of happiness that thwarts happiness.”

What Frankl knew was that you can’t make happiness out of something outside yourself. Riding a Jetski doesn’t make you happy. You decide to be happy while doing that activity, but you could as easily decide to be angry or sad while doing this activity (although Daniel Tosh would disagree!). Frankl also wrote in Man’s Search for Meaning, “Everything can be taken from a man but one thing, the last of the human freedoms — to choose one’s attitude in any given set of circumstances, to choose one’s own way.”

I get asked frequently by leaders about how they can make their employees or workplace happier.  I want to tell them about Frankl’s research and what he learned in the concentration camps. I want to tell them that you can’t make your employees happy. They have to decide they want to be happy, first. But, I don’t, people don’t want to hear the truth.

Coming up with ‘things’ isn’t going to make your employees happy. You might provide free lunch, which some will really like, but it also might make someone struggling with their weight, very depressed. You might give extra time off and most of your employees will love it, but those who define themselves by their work will find this a burden.

Ultimately, I think people tend to swing a certain way on the emotional scale. Some are usually happier than others. Some relish in being angry or depressed, it’s their comfort zone. They don’t know how to be any other way. Instead of working to ‘make’ people happy, spend your time selecting happy people to come work for you.

In the middle of a concentration camp, the most horrific experiences imaginable, Frankl witnessed people who made the decision to be happy. Maybe they were happy to have one more day on earth. Maybe they were happy because, like Frankl, they discovered that the Nazis could take everything from them except their mind.

Provide the best work environment that you can. Continue to try and make it better with the resources you have. Give meaning to the work and the things you do. Every organization has this, no matter what you do at your company. Don’t pursue happiness, it’s a fleeting emotion that is impossible to maintain. Pursue being the best organization you can be. It doesn’t mean you have to be someone you’re not. Just be ‘you’, and find others that like ‘you.’

Can I ask a favor?

We all get asked for favors on a daily basis, sometimes on an hourly basis. Most aren’t really favors, they’re just requests for something the person probably is getting paid to do or it’s their responsibility, but it sounds nicer if we say it’s a favor. I get asked for a lot of favors and I probably go overboard on trying to accommodate most. I can blame my Midwest upbringing, but honestly, most folks asking for a favor find it hard to ask to begin with and I know that. Having the courage to ask should be rewarded.

I had to ask for a favor this week. Kind of big favor (you know who you are if you’re reading this – thank you for your help!) that had to do with my business. Because I tend to give a lot of favors, I don’t feel nervous about asking, but I also don’t ever assume the favor will be granted. I go in eyes-wide-open, I’m giving favors without any guarantee that someone will be able to give me a favor back in return. But, it’s rare when someone can’t.

I find business can frequently be a favor economy. It’s not always about signed contracts and cash changing hands. In fact, most of the business I do is paid in favors, with the hope that one day a signed contract and cash might come!

The biggest favor I ever asked was when I wrote my book. I went out to my entire network and asked them to buy a book. That’s a big favor! To the tune of $24.95. I could actually put a price on that favor. The reality is, most favors we would consider much more valuable. The book favor was less about the $24.95, and more about the support of my content and all that I had given to our community for many years. The funny thing about that favor is while so many bought the book and made it very successful, not as many as I thought bought the book as I expected. Turns out, $24.95 is a giant favor to ask of some folks!

In comparison, I’ve asked folks for the favor of an introduction that has turned into a seven-figure deal for my company. That same person wouldn’t spend $24.95 on my book, but they would give me a seven-figure introduction! It’s ironic how we value favors!

Favors are the currency of our everyday business interactions. You need something from me, regardless if I’m getting paid for it or not, and if you give me a favor it almost is a guarantee that I’ll reply with a favor back. Yet, we place no monetary value on favors. Well, at least most people don’t place a monetary value on favors! But sometimes we run into someone that has a definite favor they need in return that might turn into a monetary or resource-driven favor that is really hard for us to obtain.

I’ve had many folks in my life, as a favor to me, push a candidate I was supporting in front of the hiring manager with a good word. No guarantee of hire, but getting to the top of the pile sometimes if the push you need to get some of that “favor” luck! I’ve done the same, too many times to count. We’ll say it’s just our job, but in reality, it’s more than that.

I believe it is in our nature to want to give a favor. Not because we’ll get something in return, but because we like to help others. I truly believe this is a built-in emotion of the human condition. If we can do something for you, that will help you, at a fairly low cost to ourselves, why wouldn’t we want to grant that favor? It gets a bit tricky as the cost to ourselves starts to feel uncomfortable.

No big aha moment to end on. Just simply think about all the favors you give and take today as you navigate around. It happens so often, sometimes we forget how common it is.

HR Blogger Becomes Maui Travel Blogger!

Let’s start with I’m not a travel blogger, but I like to travel and I like to think I can vacation with the best of them! I spent the last two weeks in Maui, part family trip with the boys, part anniversary trip (with no boys) with my wife and eye. I’ve traveled all over the world, but for some reason never went to Hawaii.

First, I spent all two weeks in Maui, don’t @ me! I get Kauai is “way” better and Oahu is your favorite and Oh, I can’t believe I didn’t do the big island. Shut it! After flying 10 hours, I wasn’t looking for more stupid flights during Covid! It’s a nightmare flying right now between Covid, low staffing levels, etc. I wanted two weeks of fun and relaxation and fish tacos.

Shoutout to the twenty+ folks who gave me ideas of what to do. Too many to mention, but I think 95% of the stuff folks shared with me was awesome!

Okay, let’s breakdown Maui according to Sackett

1. We stayed the first week in Kannapali (west Maui) big resorts – Marriott, Hyatt, Westin, etc. Easy for families, big pools, average hotel food, good golfing. If you like big giant hotels and a lot of people west Maui is for you. Everything is right there, it’s simple. It was good. Great weather, lighter winds. Easy to get out and spend time on the beach.

2. We stayed the second week in Wailea (South-west Maui). Wailea is higher end. Fancy resorts, way better restaurants, higher daily trade winds, great beaches, better snorkeling, felt way less busy than Kannapali. Tremendous sunsets. Whale watching right off our balcony.

Things I did on a 5 Star scale – 1 Star = Never do this; 5 Stars = Must do.

Snorkel Trips with Trilogy. We loved this so much we did it twice! Once out of Kannapali and once out of Kihei. These guys were amazing and you have a lot of options for these types of trips. Trilogy costs more than most, but it was worth it. Great newer boats, very clean, great staff, great food (not joking! one of the better lunches we had on the island!), great drinks. I actually would have done more of these they were so enjoyable! I also did Snuba on one of these trips and it was amazing! (5 Stars)

Ultimate Whale Watch was cool. We were a bit early for great whale watching but we still saw five whales in two hours. They have small boats, so everyone is basically in the front row. The crew would call around and find whales and were knowledgeable. The small boats make it easier to zip around and find more whales. (4 Stars, but only because we were early in the season, better in late January, early February, but we did see whales both weeks – 2 breaches which are unheard of)

Kapalua Golf, Plantation Course – Super expensive, but it’s always rated the number one course in Hawaii and one of the top courses in the world, and it was amazing! The views are outrageous, it’s difficult but playable. If you’re a serious golfer this is a must-do when you go to Maui. I only golfed twice in Maui and both courses had great rental clubs. (5 Stars)

– Helicopter ride around Maui – we went with Pacific Helicopter Tour and it was awesome. Now, we were hoping to do the entire island, including the north shore, Road to Hana, but the weather kept us on the west and northwest side, and it was still one of the most amazing things I’ve done and seen. You see parts of Maui no one can see and it will remind you of Jurassic Park! thousand-foot waterfalls, rain forest, coastline crashing waves, etc. Plus, flying on a helicopter with the doors off is just fun! (5 Stars)

Surf Lessons – We used Maui Wave Riders and it was good. Look, I get it, most people aren’t going to take surf lessons, but I’ve got three boys (err. men) and we like to try adventurous stuff. I’ve now taken three surf lessons: Sydney, Hermosa Beach, and now Maui. It’s hard and tiring, but it’s so much fun! You fall a lot and it can be frustrating trying to get up, but a great instructor is a key to getting you up on a board, and then you get addicted. (4 Stars – waves were good, but it’s a packed place in Lahania where you can catch them, but great for beginners)

Haleakalā Sunrise Tour – We used Skyline and they were good. So, this is very weather-dependent on how great it can be, we had a lot of clouds, but still got some good sunrise views, but not awesome. Understand, they pick you up at 2:45 am to get there and when you get there an hour early it’s 30-40 degrees, so you freeze! I definitely would not take kids on this! It’s a long day, cold, and you are hoping to get a view of an amazing sunrise that lasts like 20 minutes. Then a long ride back. The positive was the tour gives you a ton of information and history, plus they gave us warm coats, but when they tell you to dress warm, they are not kidding! (3 Stars)

Road to Hana – this one will be the hardest to rate, it almost needs multiple ratings because there are pieces of the Road to Hana that are 5 stars and some that are 1 or 2 stars. We bought an app to guide us and it was super helpful (Gypsy Guide – $10). FYI – you will need hiking shoes or shoes you don’t mind getting dirty, and most likely they’ll get wet, so bring a change of clothes as you’ll most likely want to swim as well. We left Wailea at 6:30 am, skipped Ho’okipa Beach because we had already been there, and pretty much beat the traffic out on the road, we made Hana by 1:30 pm and that was with 90 minutes at Wai’anapanapa State Park.

Here’s what we saw on the Road to Hana with star ratings:

  • Ho’okipa Beach – (5 Stars) – great surfing beach, turtles, huge shore breaks. This is like 10 minutes from the airport and is at the start of Road to Hana. Really an amazing site to see being so close to the airport.
  • Town of Paia – (3 Star) cool little north shore surf town, if you want to stop to grab something to eat, etc. But not that different than most small towns on Maui.
  • Twin Falls – about a mile walk to a fairly decent fall into a muddy pool. Private land, so you pay $10 to park. (3 stars – but after the Jurassic Park Helicopter falls my ratings are probably skewed)
  • Rainbow Eucalyptus Trees (5 stars) so cool, you get a view of some from the road, but you can also stop at Ke’anae Arboretum to get some up close pics. They are so cool.
  • Ke’anae Peninsula – (5 Stars – must stop) first Aunt Sandy’s Banana Bread is here, and you have to get some, but the coast line here is breath taking and little ocean front town is very cool.
  • Wai’anapanapa Black Sand Beach – (6 Stars) we spent an hour and half here exploring the cliffs and could have spent all day. Sure the black sand is cool, but that’s only the half of it. You must buy a pass here before you go for a certain time period. You can not buy the day of. DO THIS! We got ours for 12:30pm and actually had to drag our feet a little because we got there a bit early.
  • We didn’t even stop in Hana, there isn’t much to see, but took off for what we were told was must see things past Hana – 7 Sacred Pool and Pipiwai Trail, which both basically sucked. Plus it cost $30 bucks to do it and it was on the worse stops of they day, primarily because the water wasn’t running, so not much to see, but you don’t know that until you get there. (2 Stars – but I think that is time of the year specific)
  • At this point, most people turn around at Oheo Gulch – 7 Pools and go back, but we kept going around the Reverse side and it was really cool! Extremely narrow road, puts you a few feet from the ocean for some magical views. I would only do this with a four wheel drive vehicle, even though we saw some normal rental cars doing it slowly. It’s about the same distance getting back to the beginning but you get so much cool shore line to check out. (5 Stars) FYI – Watch out for the wild goats on the road and local drivers coming at you super fast with very little room.
  • There are a ton of road-side water falls you see on the Road to Hana and it’s probably worth stopping at a few and taking pics.

Snorkeling at local beaches – Bring, rent, or buy snorkel gear, you can see awesome stuff every day at local beaches for free. We snorkeled almost every day and spent hours swimming with sea turtles and all kinds of stuff. I don’t think there was one time I went out snorkeling that I didn’t run into a sea turtle no matter where we went.

Sunsets – Wailea has way better sunsets than Kannapali, so if you’re into amazing sunsets, spend some time over in Wailea/Kihei. Kannapali sunsets aren’t bad, but you are usually blocked by another island, so you’re getting the sunset over an island, whereas in Wailea you get full ocean sunsets.

What we didn’t get about Hawaii

Tourist bring their kids! Like a lot of kids! I’ve been on flights to Orlando home of Disney World with fewer kids! I’m not sure why people spend all that money to bring kids to Hawaii. It’s perplexing. First, it’s a miserable flight from the mainland, basically an international flight. It absolutely makes no sense! We saw non-stop meltdowns by kids and parents.

Meals basically come in two price points if you’re eating out: $50 per person and $100 per person (includes alcohol drinks). $50 per person is a basic bar food meal, think Applebee’s but in Hawaii with fish tacos. No matter where we went, after tip, it was about $50 a person. Good meals, fresh fish, steaks, etc. at a nice place push it to $100 per person. Everything on islands is expensive, but this seems strange.

Nowhere on the island is the speed limit greater than 55 mph, and it’s usually 45 mph and under. Don’t be in a hurry, you get nowhere fast on Maui.

Pictures do none of this justice! We took pics of everything and nothing really comes close to capturing the beauty of it all.

HR Blogger Turned Maui Travel Blogger Insider Pro Tip:

We had the world’s best cinnamon roles at a place in Kehei called: The Cinnamon Roll Place. I kid you not, these were to die for and I’ve had cinnamon rolls all over the world! For $5 it’s by far the best deal on the island. It’s in some little strip mall behind a staircase being guarded by a wild rooster. You can’t make this stuff up!

Okay, friends, what did I miss? Hit me in the comments!