Archive for Entrepreneurship – Page 2

Entrepreneurship is …

Two Things I’ve Learned Being an Entrepreneur and Parent

I was five years into starting and running iThemes when I added a new title to my resume: Dad.

Being an entrepreneur and a father is a very interesting combination. It brought up new issues, challenges and questions for me. In fact, it was one of the questions I went to my business group about before our first child was born, as many of them were already fathers and entrepreneurs.

My friend Ben Welch-bolen (and new father) has started a great new site called Entrepreneur Parents to share advice and experiences for those of us who are both. He asked me to chime in and I gave two answers, which you can also read here, but I wanted to share my thoughts to the questions here as well, so here goes:

With kid(s) and a business, what do you do to maintain your relationship with your spouse?

This has been our biggest struggle — simply making time for each other.

We quickly realized, no matter the cost, we had to do weekly dates. We found early on that night time dates (especially with infants) did not work well for us. We’d end up falling asleep on the date.

So now we do Day Dates, typically on Saturdays.

We can tell the difference when we skip a Day Date or simply don’t get one for a week or two. And continue to realize that it’s an investment in US, and we know the better we are together, the better we are for our children.

Plus, my mentor warned me …. we spend 18+ years raising kids and all the time-consuming activities and focus that includes … then one day they are gone, and we’re left with an empty house and a stranger.

We heeded that warning.

By the way, one huge benefit of having a physical office is we use it to get sushi and wine for lunch, watch movies, and talk on a couch while our kids are under the care of someone else at home. In the past, we would bounce around to different restaurants or places and spent more time, energy and money wandering like nomads than sitting and talking and enjoying quality time with each other. We still go out, but we know we have another “home base” to go to, something many others don’t have the benefit of.

What is the #1 piece of advice you would give an entrepreneur who is about to be a parent on how to balance those two worlds?

When I became a father, my business (my first baby) was in a good place. I tell people my busiess is now in kindergarten and under “adult supervision.” So the timing was really good to be able to focus less time and energy on my business than I did in the startup years and to shift that focus more to my children and family for a nice balance.

I have more time and energy constraints now as an entrepreneur and father, which I think is actually a very good thing. I have obsessive and workaholic tendencies and now I simply can’t (or won’t) do the things I did in the beginning, which gives me such a better perspective on life.

I’ve been able to focus on empowering and mentoring others in the business to do some of the things I frankly shouldn’t have been doing. I prioritize my time and energy so much better now.

The biggest thing I struggle with now is taking off my CEO hat when I get in the door at night and putting on the “Daddy” hat. It’s been a frustrating struggle, honestly. I’ve spent so much of the last 9 years being the leader, the one people look to, working with a team of adults and professionals, being able to give direction and know it’ll be done, that I have to reset my mindset when I’m home. I’m so much more of a caregiver, a teacher, a listener at home, but it’s also helped with business.

Patience is truly a virtue. And one I’m continually working on.


Go share your thoughts over at Entrepreneur Parents too! 


Bros, It’s Time To Hang Out More Regularly

Last weekend, I went on a quick but epic roadtrip with my youngest brother, Matt. On short notice I needed (and let’s be honest, wanted) someone to go with me to our New Mexico cabin (about a 9-hour drive each way) starting on Friday night and getting back on Sunday night.

Matt and I are seven years apart in age. He’s a police officer and I type for a living. We didn’t grow up in the same home, but we’ve always had a brother bond that even if we didn’t see each other for months, we would start where we left off.

So for 18+ hours on the road and all the in-between time when we weren’t sleeping (barely), there wasn’t 5 minutes of quiet between us. We talked about everything from children, marriage to politics and career … and of course our hopes and dreams and thoughts about the future. We toasted and drank some excellent Balvenie. We grilled veggies and steaks. And yes, there were plenty of pranks, shenanigans and laughs.

After the trip, although we were both exhausted I could not wipe the grin from my face if I wanted to.

And then after the trip, I read this article titled “The biggest threat facing middle-age men isn’t smoking or obesity. It’s loneliness.” And it got me thinking …

It’s true. At least in my life.

Yes, I have an incredible, supportive wife who is my best friend and amazing children that give me so much meaning and purpose and joy and love. Yes, I have a lot of close friends. But because of the busyness of life — career (running a business) and family (chasing two kiddos around and prioritizing my marriage), I see it’s truth.

In fact, I think you can walk the halls of many nursing homes and see this truth:

Loneliness kills.

Here’s a couple of quotes that stuck out to me from the article:

“Loneliness has been linked to an increased risk of cardiovascular disease and stroke and the progression of Alzheimer’s.”

“In 2015, a huge study out of Brigham Young University, using data from 3.5 million people collected over 35 years, found that those who fall into the categories of loneliness, isolation, or even simply living on their own see their risk of premature death rise 26 to 32 percent.”

As I read further in the article, I saw more truths:

Men need an activity together to make and keep a bond.”

“That’s why Schwartz and others say the best way for men to forge and maintain friendships is through built-in regularity — something that is always on the schedule.”

The key takeaway from the article hit home with me: We, men, need a regularly scheduled activity, especially in mid-life. 

So it got me thinking about how I’ve tried to find that male bonding time …. and here are my thoughts.

My Goals for Guy Time

Just replacing on the activities with other friends, here are the most valuable values I have for those relationships that maximize those times:

  • Go deeper — the older I get the less I care about small talk. I want to get to the deeper issues of life. My best friendships are the ones where we skip the surface and talk about the iceberg of life — both the struggles and successes.
  • Be more open — my most valued friendships are the ones where I don’t have to wear a mask or a costume. I’m just me, being me. And vice versa. This is all about trust and respect. And no judgment. We all have skeletons in the closet. The most incredible experiences I’ve had is two humans being human together. Recognizing we all have emotions and feelings, hopes and dreams, whether they seem trivial to us or not. I’ve found I’m my worst critic and whenever I’ve been more human and open, I get open and human back.
  • Make lifetime memories — have fun and enjoy each other’s company. The best times are when we’re doing something fun, whether it’s white water rafting in Idaho (or New Mexico) or simply enjoying a drink while telling stories that become our legends. Life is so much about the moments you share.

Some Ways I’ve Found That Bonding

Here are a couple of ways I’ve found that CONSISTENT and ongoing time with my dude friends:

  • Monthly Mastermind Meeting — although it’s not a mastermind (and we have females in the group), for the last 5+ years, I’ve been meeting with a group of 8-9 Oklahoma City entrepreneurs (via Entrepreneurs Organization) every month for three hours. They’ve been my lifeline of sanity as well as success. It’s been so incredibly impactful on my success and sanity that I’ve also started another forum group in the past, and am in the process of seeding another one this year. I’ve found nothing like it in the world. Like-minded people, in similar stages of life, with the same values and goals, setting aside a block of time each month to work on our icebergs and share our lives with each other. The other one I’ve been a part of like this is one with five other WordPress peeps, but is mainly focused on work/career accountability.
  • Once a Year Retreat — Our Entrepreneurs Organization Forum group also does a retreat once a year for 3-4 days, typically in the summer around June. We’ve done some fun stuff together like fly fishing in Montana to flying jets in Vegas, but it’s always the times around the campfire that mean the most to me. I also look at PressNomics and CaboPress (conferences I try not to miss) as times for bonding with my business friendships. I shouldn’t even label them as ‘business,’ they are friends I’ve made through business.
  • Team Sports — I just recently returned to indoor volleyball, a sport I’ve loved since college, after the urging and push from my wife. In the past, Lindsey and I have also played softball and relished those new friendships and times. Although the team was co-ed, I enjoyed the camaraderie and bonding and looking to playing volleyball again in the summer season.

Filling in the Gaps with One-Off, Somewhat Random Opportunities

  • Roadtrips — my brother Matt and I are already planning our next roadtrip over the weekend. Watch out Moab, we’re coming for you in Jeeps! In August, we’ll be joining our dad and other brother and friends to go hunting in New Mexico. (I don’t hunt or like to hunt, but I won’t miss another trip with these awesome men.)
  • Lema/Miller Slumber Parties — my buddy Chris flew to Dallas to hangout with me for a couple of days and because we’re kids like this, we said it was our Slumber Party. We talked until way too early in the morning and had to force ourselves to go to sleep as it was so much fun. Slumber Party Party Deux is in a couple of weeks. I know, we’re geeks, but proud of it!
  • WordCamps — the Hallway Track is my favorite, especially at WordCamp US. It’s hard to get 5 feet before you’re talking and catching up with some awesome WordPress community friends. Some of my favorite memories are hanging out (and getting lost on subways) with guys like Michael Torbert way back at WordCamp Boston, or sharing one-on-one time with guys like Karim Marucchi over a good meal.
  • Portugal Pals — one way my COO and buddy Matt Danner and I stay close and in sync is through regular trips together. There’s something about flights and hotel rooms without much distractions that are always a blast. We just returned from a once-in-a-lifetime, epic trip to Portugal. #pals
  • Dad Dates — my buddy Jesse and I have children the same age AND gender. He graciously went with me to see the latest Star Wars movie recently. I also had dinner and got to see the OKC Thunder play (courtside, holy cow!) recently with my buddy Jeff. It’s awesome when you are in parallel life stages, and going through similar things.
  • Coffees and Lunches — I enjoy catching up with my buddies and making new ones (like I did recently when John reached out to me as he was traveling to OKC for a wedding).
  • Traveling — on our personal trips, Lindsey and I have a motto and mission: Make friends everywhere. And we have. I love making new friendships with those in new cultures and around the globe. It’s entirely changed the way I do traveling now. My goal isn’t just to see new places, but to meet new people. It’s so mind expanding and special. Our friend Marco and his family, on Father’s Day, took us on a full-day tour of Lisbon, Portugal. So much fun memories — made even more special when his mother gave us tiles that goes on her house (a very cool Portuguese tradition).
  • Partner Pals — some of my best memories of my business partners, Scott and Jay, have been on our trips, whether it was to visit the campus of Google and Yahoo or the White House. I want for more trips with these awesome men and role models.
  • Skype, Slack, iMessage chats, Facebook — it’s never a substitute for face to face, or elbow to elbow bonding times. But the article says men aren’t great at talking on the phone (I hate it) yet throughout the year my buddies and I seem to stay in touch via these text chats. My friend Jason is great at keeping up like this.
  • Reunions — after 20 years of not going to my high school reunion, I went a couple years ago and thoroughly enjoyed catching up with old friendships, although I have not kept in touch beyond liking their posts on Facebook.

Ideas for More Consistent Hang Out Times:

  • Once a Month In-Person Coffee or Breaking Bread — like every third Wednesday. It’s way easier for me to do lunches or daytime meetings than nighttimes with kids.
  • Once-a-Quarter Weekend Trips — very short roadtrips that get us away from the distractions of life with a focused activity — like watching a football game, or
  • Once-a-Year Retreats — as I mentioned I already do this with my Forum group … but another in a year would be super nice, like 2-3 days away.
  • Movie Night — whenever a new movie comes out, we go see it on Thursday night — if we can stay up that late!

Additional Thoughts and Caveats:

  • Spousal/significant other support is essential — My wife is my top relationship priority. Without the support of my wife, I wouldn’t do the things I already do, but thankfully she sees the value for my life, health and happiness, and I do for her retreats as well. We try to do regular checkins to communicate and see how we’re doing, one of the many reasons I’ve tried to winnow my business travel down drastically this year.
  • Too much time away — I realize with all these ideas, at some point, you can spend WAY too much time away from your family, which ain’t good. It’s all about time budgeting and again talking it through with your spouse and family. It’s interesting to note that Lindsey and I try to do these kinds of spousal retreats and getaways as often as possible. She comes first, always and forever.
  • Getting overscheduled — I try to have as few regularly scheduled meetings in my professional life as I can (let alone personal), and if I were to add too many things above, I’d get way too booked up, which would mean less time for family and family travel.
  • Prioritizing relationships — I realize there’s a limit to how many close relationships one person can build. Proximity is often the prioritizing factor just because it’s easier. Lema talks about how he approaches that here.
  • Gal Pals are just as awesome — over the years I’ve had so many special relationships with some awesome, wickedly smart, incredibly supportive ladies. I’ve found just as much joy with my gal pals and don’t want to leave them out in any way. In fact, looking over my Instagram feed for pics showed me how much time I have spent with these awesome awesome women.

OK, what are your ideas?


Need Some Clarity? Schedule a Call With Me

For some time now I’ve gotten regular requests to do phone calls and consulting. I enjoy talking, listening and helping people, particularly entrepreneurs and young people looking for career direction.

Today, I’m taking a step to do that even more, by setting up my expert profile at Clarity.

Sometimes it just helps to get an outside perspective and opinion from someone who’s been there and done it. And I want to help you blow up the roadblocks in the way of your happiness and success, sharing my experiences to help you do just that.

If that’s you … schedule a call with me today and here are three ways I can help you best:

Schedule Your Call Today!

How to Be a Professional:  12 Tips to Thrive at Your First Job

In the past couple years of leading and “managing” people, especially young people right out of college, or those who haven’t had many jobs, I’ve seen a gaping hole in the form of teaching people how to be a professional. (Maybe it’s always been there but either way, it’s there.)

When I think about this topic — helping young people know how to survive and thrive in their first jobs — I think about star college athletes who are drafted into the pros. One day, they wake up and find that their lifelong passion (football, baseball, basketball, whatever) — the thing they’ve always done without much effort and with outstanding success — has now turned into a full-time job tied to all their lifelong hopes and dreams. And often it’s the job of the veterans to teach the rookies how to be a pro.

It’s usually someone’s job to help the “rookies” figure out how to be a “pro.”

So with that … I’ll offer my suggestions for the next generation to succeed in the workplace (and be a little blunt):

1. Be passionate

This means being interested in what you’re doing. Do something you have a great opportunity to LOVE.

If you take a job simply because it’s a crapload of money, I’ll make a bet now you’re going to be miserable in 10 years if you stick with that job. Don’t waste your precious time or talent on a job you hate simply because you want a BMW.

Take a cue from your Baby Boomer parents … happiness isn’t found in material things.

Loathing or hating a job is misery … that’s called prison.

You don’t necessarily have to love what you do … but I think you should at least LIKE IT.

Find a job you can like or enjoy, doing work that challenges you and plays to your strengths.

2. Be eager

I hire for drive and fit over talent. Being eager means you are internally driven to make your organization a success and with it, yourself. You should want the job. You should want to work hard to keep it and be better.

Being eager is typically a result of doing work you enjoy. Looking forward to going to work because you want to use your time and talents to produce something of quality.

3. Be a sponge

Just because you’ve graduated from college doesn’t mean you stop reading for the rest of your life. Be a lifelong learner. After you get over your college “I hate books” hangover, get realistic and realize that the key to growth comes cheaply by reading dead trees.

So if you’re not a reader, become one.

A key core value we hold close at iThemes is Learn, Grow, then Share.

Always be learning. Always be growing. Seek ways to do so. Find mentors at the workplace and ask questions and listen. Buy their lunch, make and bring them their morning coffee.

But by the way, listening is so undervalued. Most people want to talk about what they do best.

Be a sponge for all of it.

4. Get better on our own time and dime

Someone should tell you this and it might as well be me: You haven’t magically “arrived.” You probably won’t ever arrive. Neither will I. At least I hope I don’t or think I ever will. I always want to be improving and honing my craft.

Just because you land some fancy title doesn’t mean you’re set for life or done learning or growing.

Graduation is simply the first step in a journey that’s called your professional career. Now it’s time for you to use that base knowledge and those experiences to build your career.

It means constant improvement. And if you want to make more, do more, then that means you hone your skills on nights and weekends (yes, on your own dime!).

Let me be clear: Getting better at night and weekends is an investment in yourself.

If you learn and grow, when you get another job, you TAKE that with you. It’s yours.

You always want to achieve work-life balance and you need downtime … but consider using a large portion of that time investing in yourself.

Trust me … as a boss, this type of team member rises to the top. They are the clear leaders you take for the future of your organization. At least I do.

5. Everybody starts somewhere

Call this paying your dues or whatever, but yes, everybody starts somewhere and typically that’s at the bottom of the ladder. That might mean taking out the trash, being someone’s assistant, taking direction from someone else, or whatever.

You aren’t above it. And neither am I. Even as the founder of a company, I still do these things.

If you don’t have the humility to accept that, you’re going to struggle for a long time. You might even think it’s not you, but everybody else. 

Realize now that this is the first step to a great adventure. Use this time to figure out what you want to do in your organization and in life. Solidify the place you want to be in and work hard to get there.

6. Be the solution

No one likes a complainer. Be a change agent instead. Be someone who sees a problem and owns the solution.

Initiative is an amazing, standout quality. The majority of people simply point to a problem and see if someone else comes to fix it.

A lone minority see the problem and realize they could fix it themselves and try. To them, go the rewards and recognition.

I want 100 more people like that in my business and in my life.

7. Be flexible

Flexibility and adaptability are assets in your career. Things won’t always go your way or the way you expected them to go. Sometimes you might be asked to work late, or switch roles, or do something your job description didn’t talk about ….

Be willing to adapt and change if needed.

The people who are the most flexible and adaptive, who just want to contribute and provide value, are the ones who rise above.

8. Be helpful

Yes, this means changing the printer cartridge, or taking out the trash. It means answering the phone when someone isn’t close to it.

It means helping someone else with their problem, even if it isn’t yours. 

As a boss, I want a group of individuals who WANT to help each other. Who want to help their teammates take their vacations and will work to fill the gap so they can do so without worry. Or who understand we are all humans being with struggles and challenges and needs … and there to be helpful and generous with our time and energy.

9. Be on time

This should be implied but I’ve realized it’s not. Show up for work on time, every time, and even before time. When you walk in late, it shows a lack of respect for everyone else.

When in doubt, ask what the expected times are. And be early and stay later. It adds up. People see it. It shows commitment.

I did that in every job I had and it paid off richly in terms of my value and reputation. Because I simply showed up.

And by the way, just because other people on your team don’t respect this and are habitually late doesn’t mean you follow the herd.

10. Find out how you fit in, quickly

Like I’ve said before, we hire for fit over talent. In a small business especially, it’s vital that you fit in. Otherwise, you’re simply a distraction.

Find your unique place, quickly. Discover your unique role in your organization and what you can contribute to it. Look for the place where you uniquely help others be better and where your talents and strengths are best suited and plug into that.

11. Show up, work hard and you’ll standout

Don’t shortchange your organization by not showing up — and I don’t mean simply skipping work. Although being mediocre, giving partial effort is the same I think.

If you agree to take a job, with specified hours, pay and responsibilities, do your best, every day. That’s what you agreed to when you got the offer, so be a person of your word and honor it. (Some of the best advice my father gave me.)

And let me give you a hint …. do more than expected. It makes you stand out and people will take notice in a very positive way. 

By the way, conversely, doing the bare minimum makes you stand out in a completely opposite way.

12. You’re not a rockstar

Companies and businesses might say they want to hire “rockstars” but I’ve found those with the rockstar mentality don’t usually work well in teams. Rockstars are about themselves and their own fame and fortune. They are solo acts and that is divisive to teams.

Be the opposite of a rockstar … be a team player.

This African proverb says it all: “If you want to go fast, go alone. If you want to go far, go together.”

On average, cohesive teams will always do more and go farther than rockstars in their selfish silos. Join a team and be the glue or compass or role player (whatever it takes) that makes you all better, together.

BONUS TIP: Get a job before your first “career” job.

If you’re still in college, I’d highly suggest you get a job, an internship NOW. Yes, before you graduate. Start working somewhere so you can learn what it means to make money for your time and talent … and how to work with other human beings … and under the direction of someone else.

Our awesome developer Chris Jean, one of the hardest working and talented people I know, often says that working in the fast food industry was one of the best things he ever did. It forced him to develop work habits that we now benefit from. For me, that was working alongside my father, uncles and grandfathers in their businesses. 

So You Want to Work Remote …

I have a couple of disclaimers as well as context before diving into my thoughts on working remote.

First, this post is written from a manager’s perspective, not the team member’s, particularly my own as I’ve led and grown iThemes from one person to now over 20+ since 2008. I’m focusing these thoughts and experience sharing on a situation where you (a current team member) are wanting and requesting to go from working in a dedicated office to working from home or “remote.”

Additionally, we’ve been a hybrid team from the beginning — with remote team members and in-office team members. (We currently have a 5,300 square foot office in Oklahoma City, that we call iThemes HQ.)

It’s all written in the context of a small bootstrapped company, who has been in business for 9+ years. I know a lot of companies, particular Automattic, have very progressive perspectives and expectations on remote work. But that’s not us and we don’t expect them to be us either. Every company and situation is different.

But in that context as a small team, we’ve seen what seemed like minor changes have drastic and negative effects on our team and HOW we get our work done.

We have a really really really good team who collaborates and communicates well and is extremely productive. And because our culture is very important to us … we’re very guarded and careful how we make changes to that as it’s vital to our continued success and health.

Our job and responsibility, as managers and leaders (just as your managers), is to ensure every team member, whether in our office or remote, is connected, productive and fulfilled in their job and work.

And ultimately our charge is to do what’s best for our company, team and customers and to evaluate each request situation carefully to ensure maximum success for each team member, our greater team and our company.

And yes, we’ve made mistakes and learned lessons that I want to share so you have the best chance at success.

We have a very diverse variety of team members, work, teams, and setups. They don’t and won’t work for everyone, in every situation or position.

My hope is this post will help you prepare and frame your requests in your unique position and situation and leadership, as well as prevent the problems and mistakes we’ve made and seen in the past.

The following are the things I think you, as a team member in your own organization, requesting to go remote, should be prepared for and consider as you move forward with those conversations.

Much of this also applies to in-office team members too, by the way, but there are some key things that managers do to ensure that success that often get taken for granted. For instance, we lock our office up tight. We have a doorbell that rings to our Office Manager’s office very softly. She is the distraction-cancelling protector of productivity. She knows that any time there is a disturbance or distraction in our office, we all lose.

So take it from that perspective ….

Some Thoughts and Ideas I’d Mention Upfront to You:

  • Realize remote work is NOT for everyone, every situation, or every position — Some of the most social people I know think they will be happy in a quiet home office with no regular interaction with other humans. Additionally, some job or teams may not simply be ready or right for it.
  • Know yourself, search yourself — All of this is an effort to make sure this is a win for everyone. But that starts with knowing yourself. And more importantly … WHY you’re wanting it.
  • Ask for and expect a trial evaluation period — Or even starting with one day a week. Be open, honest and transparent about how it goes. If you just give a report of all roses and no thorns, it’s liable to raise suspicion. No environment (even a dedicated office) is perfect. Far from it. Give the pros and cons, the opportunities and obstacles, the good and the bad.
  • If you’re really green, with lots to learn, this might not be the best for you — We’ve hired a number of people in our office we would never have hired remotely. Namely because they were rookies, with lots to learn and needed the mentoring and coaching that happens more easily when you can simply roll your chair over to a veteran and ask questions. Including at lunches, breaks, etc. If you’re just starting out into your career, check out my How to Be a Professional primer, before moving on. 
  • Understand that failure could mean jeopardizing your job — If it doesn’t work out, there’s a likelihood beyond requesting you come back to the office, that you’re also out of a job. And ALL  of the things I’ll mention here are to help you have the BEST chances to not just survive, but thrive, from a manager’s perspective.

Key Questions I’d Ask You:

  • What’s in it for you? I probably already know this already. But what are the benefits for you and the reason WHY you are requesting it?
  • Where specifically will you be working?
  • What is your remote setup specifically? Do you have a dedicated, private, distraction-free home/office setup?
  • Are there other people who will be in the same space during your work hours? (i.e. your home, kids, spouses, roommates, etc.)
  • How will you manage work/home/life boundaries and distractions? Goes both ways …. if you’re officing out of your house, that’s the same place you sleep.
  • What’s in it for us? The company, your teammates, your work? I ask this because most of us get what’s in it for you … but rarely think about it from the company and team’s perspective.
  • Why do you think you’re ready for this? If this isn’t crystal clear for everyone, then it becomes a rhetorical question.

The Key Dangers Of Going Remote I’d Mention To You:

These dangers are specifically in taking an otherwise great productive teammate and potentially losing or damaging all of that. These are the dangers that I’ve seen and to look out for.

  • Getting lost, disconnected, disengaged — One of the biggest complaints we’ve heard from our remote team is feeling disconnected from the team and each other. This is the toughest one for us. It’s not always anybody’s fault, just nature of the beast.
  • Getting distracted — From the laundry that needs to be done to the dogs insisting on sitting in your lap during a work call.
  • Poor communication — I’ll talk more about this, but going dark, not sharing with others what you’re doing.
  • Getting stuck and spinning your wheels — Not sharing struggles so you can get and receive help and move on to productivity.
  • Not maintaining good work/family boundaries — Not just from a work perspective of ensuring family members in your house know when you’re “working” or off, but if you’re officing out of your bedroom, for instance, when you go to bed, you can still see “work” and sometimes “worry.”
  • Not maintaining consistent work schedule or routines — I believe there are few people who can work haphazard hours and still be productive. It also rearranges the purpose of work … are you working for a team and company, or is the team and company working at your whim?
  • Not approaching it as a professional — Professionals show up, get the work done, communicate with their team … and frankly, take work as serious as it should be — the thing that allows me to buy a home, or food, or pay for my children’s college and my retirement.
  • Having the wrong mindset, attitude and approach about it — this goes back to the “What’s in it for us?” question. Make sure you deeply evaluate your attitudes and reasons for being remote.

Key Expectations and Responsibilities Of Being Remote I’d Expect:

  • It’s your job to make this a smashing success — It’s not my job either, but I want it to be a success. So make this an overwhelming and obvious win for everyone, not just you. If the promise is that it’ll enhance productivity, prove it.
  • Have a dedicated, private, consistent work space with good, reliable Internet — a comfortable private place without interruptions or distractions. We can control what happens in the office for the most part, but won’t know about them at your house or remote office. A key thing we’ve learned is setting good boundaries.
  • Good communication is non-negotiable — Going dark and off the grid does not instill trust and responsibility in your team. You should not assume anything, clarify it and overcommunicate. Like if you’re away from your computer for a time (taking a child to school, or an errand that may run long, etc), you should let everyone who relies on you, and ESPECIALLY your manager, know that you’re out. And if it’s longer than expect, talk to your manager about it first. This is even more of a priority for those positions where you are collaborating and communicating with other team members to get projects done. Don’t assume your team knows that you have ran out on a quick errand, or need to step out. I’ve heard it said — communication is oxygen for a team. It’s true. And even more so for remote teams. And conversely when you don’t communicate well it becomes distracting and damaging for everyone.
  • Availability and responsiveness is a must, especially in collaborative teams — Meaning if others rely on you to get their work done, you gotta be there and show up with them. For our team that means being Green on HipChat (the chat tool we happen to use today) and working set hours so the rest of your team knows when they can expect you, ESPECIALLY if you’re in different time zones. Additionally that goes back to other things like having access to good, reliable Internet, not being distracted by people in your remote office (i.e. caring for children or other family members or people), and establishing good boundaries.
  • Routines are everything — You may not think about it, but the structure of an office provides for many things that you will not have by default as a remote team member. One of our remote team members told me he makes sure to put on his shoes every day. For him, it’s a routine and a signal that says, “I’m at work.” Ditto for set schedules. When I first started iThemes, I was working from a home office and kept my same schedule, the one I’ve maintained for the last 9 years.
  • Traveling is disruptive and distracting — So don’t plan on it. Many people are allured by the thought of being remote so they can travel the world, or work from a hotel room off by a beach. It doesn’t work, especially if you have a very involved job, or have to take calls or attend regular meetings. I know because I’ve tried it. At best, I’m 50% productive as being in a fixed location with reliable Internet and set routines. Traveling is disruptive to routines and work, no matter how good you think you are at juggling it all. Nothing goes to plan. Flights get delayed. Time zones disrupt fixed expected schedules. And yes, you can NEVER rely on hotel or AirBnB for reliable or fast Internet, or being able to get to a coworking space in a new city. So if you want to travel the world, take your vacation or Paid-Time Off for those things and get real rest and recharging that comes from being away from work that you need.

OK, that’s it for now … I readily admit I might have missed some things and as always reserve the right to change my mind. But I hope this is helpful for you as you navigate working remote in your situation. Good luck!