Lessons On Serial Entrepreneurship From the Collective Behind 8 Successful Brands

You’ve probably heard founder stories that either involve a single owner who orchestrates the various moving parts of a business, or a duo of co-founders, where one generally steers the product and the other manages the day-to-day operation.

But a third pattern is emerging, especially when it comes to serial entrepreneurship, and it’s driven by the idea of a “collective”: a group of friends or co-creators, each bringing their own skills and experience to the table to collaborate on a variety of ventures.

It’s these groups that are oftentimes the most well-equipped for serial entrepreneurship—starting multiple, different ventures more for the joy of building successful businesses than merely running one.

Serial Entrepreneurship: Why Stop at One?

Among the world’s 960 self-made billionaires, 830 are serial entrepreneurs who have founded multiple business. These include notable entrepreneurs such as Richard Branson, Mark Cuban, and Elon Musk.

If anything, that’s proof that success isn’t the end-all of the desire to start that draws people to entrepreneurship in the first place.

As they figure out winning formulas, serial entrepreneurs hand off the day-to-day responsibility of running each business in favor of starting new ventures, collecting experience, resources and talent as they go.

Shore Projects is a successful watch brand, inspired by the beauty of the British seaside, that lets wearers easily swap out watch straps. It was also a past winner of Shopify’s Build a Business competition. But what many wouldn’t guess is that it’s only one of at least 8 other businesses their team has built.

I talked to James Street, one of the co-founders of Shore Projects, about his team’s past endeavours and their latest venture, Old Harry, to find out how they managed to build so many different businesses including:

  • Brydon Brothers: A quality handmade belt brand.
  • Whalar: An influencer marketing platform, a unique member of their portfolio.
  • Boho Chien: Collars and accessories for the free-spirited dog.
  • Koala Hoodie: A Kickstarter project for the ultimate hoodie for the practical traveler.
  • Ora Pearls:  A pearl jewellery brand owned by a jewellery designer.
  • Old Harry: Their latest foray into knitwear.  

This is a team that has built successful business after successful business, an example of serial entrepreneurship enabled by a like-minded, diversely-talented group of people building things together.

Where Did It All Start?

According to James, he and Neil Waller—one of his business partners for Shore Projects, Old Harry and many other ventures—first met in university.

“We quit the third year to start our own businesses, worked together and travelled around the world for a business we started called My Destination, an online travel guide, which took several years and trips around the world,” James said.

my destination
My Destination is a travel site that was James and Neil’s first business, and helped them ditch the 9-to-5 rat race altogether.

Shore Projects, however, was their first jaunt in ecommerce and was formed when Jono Holt, who was already involved in the marketing space, joined James and Neil.

Jono contributed a set of skills (branding) that complemented James (product) and Neil (operations) for Shore Projects.

And over the course of several years, the collective of people and talent they could draw upon has only grown as their portfolio of brands did too.

Why One Successful Business Wasn’t Enough

“I think annoyingly for me is that if I have an idea, it really irks me if I see it done by someone else,” James said when asked what motivates him to start business after business.

old harry
Old Harry is one of their latest businesses, this time building a quality knitwear brand.

“I like to feel like the first. Obviously I’m not not the first to invent a watch or start something like Shore Projects, but at least we saw a difference in the strap changing mechanisms and we were kind of the first to really push on that in the watch space.”

But it’s not just the desire to start that makes serial entrepreneurship appealing to James. It’s also that the foundation for starting new businesses became stronger with every attempt.

“You need the same sort of setup whether you’re running one business or three—so we needed a designer and we needed a developer. And we had those on hand full-time, so we felt we had the capacity to take on more brands.”

Serial Entrepreneurship as a Lifestyle

When asked if starting new businesses would be a recurring part of his life, James jokingly answered, “Annoyingly, yes. Definitely.”

And it comes down to the thrill of starting: “I have ideas every week that I want to execute because in all honesty the fun part is starting up the business, getting the brand out there and selling it to people and seeing if it works. It’s not in the day-to-day running of the business and that’s probably one thing that I need to get better at. Getting the right team around you helps with it.”

But not all of the ideas they work on are their own. They’re also big on helping other entrepreneurs get their businesses off the ground.

“We’ve got another brand called Brydon Brothers that we work with in a slightly different capacity where a friend came to me and said, ‘I want to start my own belt business and I love what you guys have done.’ And we went, ‘Okay we’ll help you do it’.

brydon brothers
Brydon Brothers, a handmade belt brand, was a friend’s business idea they brought to life.

They gave them access to their designers and other resources and brought the business to life.

When building other people’s ideas, James stressed the importance of who you choose to work with: “It just depends on getting the right people behind that brand. You don’t want to end up running it yourself.”

And that’s a wise choice considering the number of businesses they’ve built and successfully launched.

Juggling Several Businesses And a Personal Life.

Starting your first business likely means you’re doing it all—at least until the money is right and you can start handing off aspects of it. And that can still be the case when you’re starting your second or third, at least until you figure out a system that works.

“Certainly the hours in the beginning were difficult,” James notes, “But again, it’s working on something that you’re passionate about. I’ve honestly now found a very good work/life balance. I don’t find myself working myself into the ground.”

Learning from their past venture, the group made the conscious decision not to over-extend themselves, spending a lot of time fulfilling retail orders and trying to “grow, grow grow as fast as they could” as most entrepreneurs might.

Instead they chose to focus only a few big retail accounts and their online store, taking their time to grow, which made their lives easier.

James says another helpful bit of advice was to be ever-aware of what you’re good at and what you’re not-so-good at. If you’re a better programmer than a salesperson, then you complement your weaknesses with the right people.

As a manager overseeing the whole company, James reflects, it’s about having a vision for the business and “not getting your hands dirty in every specific thing”. As a product guy, that’s where James gets his hands dirty. It’s his favourite part of starting a business, after all.

“I’m not a Facebook advertising specialist so I outsourced that side of the business. I’m not a great Google AdWords specialist, so I outsourced that side of the business, and all of those things kind of come together.“

Outsourcing, it turns out, was a huge part of the process when building their permanent team.

Read our Introduction to Facebook Ads for Ecommerce to learn how to do your own advertising on Facebook.

Building a Team That Builds Businesses

After ten years of working on their own businesses and outsourcing to various people, James and his business partners have managed to hold on to the best talent, the best people, to build out their team.

The process typically went something like:

  1. Hire talent on a freelance basis.
  2. Work with them over time and see how they do.
  3. If you like them, hire them full-time.

“We have two support people, we’ve got a marketing person who largely works with Instagrammers and manages the Facebook ads and stuff. And then we’ve got the designer and we’ve got a full-time developer, and myself that works on product design. A lot of them are used in different areas, in different businesses as well.”

They’ve also got a finance person who worked on their original business, My Destination, who James identifies as an essential part of their journey and growth as a collective.

With Shore Projects growing super quickly, one of the early mistakes James identifies was that they weren’t focusing on the numbers as much as they should have.

“I think that is key to any business so that would be a surprisingly good first hire. It’s certainly something that we learned at Old Harry that the cost is always double what you think it will be. You think you buy a product, say twenty dollars, but then you’ve got to ship it too—you’ve got to buy the labels for it and you’ve got to put it in packaging, then there’s the cost to post that package out to the customer, all of those things that you just don’t think of when you’re creating a business model and can add up very quickly.”

James deems this numbers-driven perspective an essential part of what they do: “My passion is developing new products. But then I have a finance person to tell me, ‘You can’t be developing new products all the time’, so there’s a nice balance.”

Standing Out From the Competition

The best competitive edge, according to James, is to not just offer a good product but a good “value-for-money” product as well.

He says the inspiration for Shore Projects came from a watch called the Animal Watch that made changing the straps really easy. But they hadn’t really seen this kit mechanism on higher end watches so they sought to make it happen with Shore Projects.

“I think that people do get bored with their watch quite easy and want to change it up and [Shore Projects] allows you do it,” James said, explaining the thinking behind the brand.

It was a similar story with Old Harry, as James has a personal interest in knitwear, but couldn’t see a brand that’s just focusing on knitwear, and felt that deeper focus was the direction more brands were going in.

“The way that we like to do it is focus just on doing one thing and doing one thing well so for instance you get your Ray Bans glasses or Calvin Klein boxers. You’ve got the Levi jeans. Those guys are doing one thing very, very well rather than creating a whole range of clothing. So we’re just going to focus on knitwear, focus on the detail and make sure it’s really, really good at a decent price.”

koala hoodie
Koala Hoodie is one of their latest Kickstarter projects and is the perfect example of going all-in on creating unique value at a reasonable price.

Cross-Promoting Vs. Keeping the Brands Separate

With several brands under one roof, it might seem obvious that they’d leverage existing audiences to promote new projects. But James says they try to keep their brands separate from one another as much as possible.

“We do a bit of cross-promotion but we just don’t actively say that it’s from the same team. We say things like, ‘Our friends at Old Harry’ when talking about another brand. Which it kind of is—It’s someone running Old Harry full-time, it’s not me running both businesses full-time.”

Check out our mates @shore_projects and use code ‘SHORE15’ for £15 off all OH purchases until the end of June ⚓️

Instead, it seems that with every new business they start, they take their learnings from the past. And in the case of marketing, it’s what they’ve identified as the best way to repeatedly leverage influencer marketing.

Influencer Marketing: A Versatile Strategy

We’re not ones that just splash the cash on people with millions of followers if they don’t look right for the brand.

“Getting the products on the right people” is how James describes their biggest focus when it comes to marketing across their various projects.

They’ve identified Instagram as a channel that they can continue to bet on for most of their ventures.

“We work with a tool called Whaler, set up by my business partner Nick Waller and created out of Shore Projects, which helps you search for Instagrammers easily and negotiate deals with them.”

whalar
Whalar is a unique member of their portfolio, an Instagram Influencer marketplace born out of their own influencer marketing.

While they do traditional Facebook and AdWords advertising, influencer marketing has been the most cost efficient way to promote their products, according to James.

But their approach comes down to finding influencers who look right for the brand, not just the ones with a high follower count.

“We’re not ones that just splash the cash on people with millions of followers if they don’t look right for the brand. I think that it’s detrimental to the brand if you do that.”

Read Nick Waller’s A Beginner’s Guide to Influencer Marketing on Instagram to learn more about how to work with influencers.

Beating “Shiny Object Syndrome” When Building Several Businesses

We’re basically an incubator and help each other get from one startup to the next.

Serial entrepreneurship can be a slippery slope as you lose focus on an existing business to pursue another one.

James, like many entrepreneurs, is always abuzz with new ideas and credits Evernote as his go-to tool for collecting his thoughts.

But to overcome the potential loss of focus in each business over time, James also says that behind each of the brands managed by the collective there is a trusted person in place who’s dedicated to running that business full-time.

ora pearls
Ora Pearls is another friend’s business idea given life, this time for a jewellery designer and pearl specialist.

It’s not like he’s juggling 8 different businesses himself. Rather, he says, “We’re basically an incubator and help each other get from one startup to the next. We’re all sharing some resources in a sort of ‘colony’ that shares the same office space together.”

Starting a Business Again. And Again. And Again

As James says, it’s the thrill of building something new that can be one of the primary forces behind entrepreneurship.

But what makes the businesses in the Shore Projects and Old Harry family so special, and so successful, is the team behind the execution as well as the environment of working with close friends in one office to bring ideas to life.

It’s the perfect example of serial entrepreneurship as a lifestyle you share with friends that’s about doing fewer things alone and starting more things together.

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34 Time Management Tips for Busy Entrepreneurs (by Experts)

Effective time management is important for anyone but it’s absolutely crucial for entrepreneurs.

Because entrepreneurs are ultimately responsible for every aspect of their business, allocating the right amount of time to the right tasks is critical to keeping your business running smoothly.


Better time management isn’t just about working harder, it’s about working smarter. We asked 34 productivity experts to share their best time management tip. Use this list to experiment and find the tips that make the most sense for you.

shopify-author Pat Flynn

 

Pat Flynn

www.smartpassiveincome.com

 

“Just-in-time-learning” changed everything for me.

“Just-in-time-learning” changed everything for me. That is, I only consume content related directly to the next task I have in the current project I’m working on. Blog posts, podcast episodes, videos—they must help me with completing that next task on my priority list, or else it doesn’t deserve my attention…at this moment.

FOMO (fear of missing out) does make this hard though, because there’s so much great stuff out there we don’t want to miss, however if you’re smart about it and as you come across interesting and potentially helpful content you put it aside into a tool such as Evernote for easy access later, it can truly change how much you get done versus how much you learn.

Just think of all the content you’re consuming—are you actually putting 100% of that into action, or are you wasting time learning things you don’t need to know right now?


shopify-author Elizabeth Grace

 

Elizabeth Grace

www.reallifee.com

 

Know your personal and professional priorities and plan your priorities in your calendar. Everything else needs to fit around them or be dropped.

Get a great assistant you can delegate scheduling and other routine activities to. This person can be one of your biggest productivity boosters and stress reducers.


shopify-author Craig Jarrow

 

Craig Jarrow

www.timemanagementninja.com

 

Just Start

Most entrepreneurs never really start.
And most business ideas end before they ever truly begin.

Stop waiting for the perfect time…. there isn’t one.
Stop waiting for the perfect product… launch with a minimal one.
Stop waiting for someday… it will never come.

You can’t finish… if you never start.

Craig Jarrow quote graphic


shopify-author Maura Thomas

 

Maura Thomas

www.regainyourtime.com

 

Reframe your thinking. Time management is an outdated idea, and attention management is the new path to productivity. How you manage your time is only relevant to the extent that you also control your attention on the task at hand. This is because if you allocate time to a task, but spend that time switching among several different tasks, the end result will likely be different than what you intended. Controlling your attention means effectively managing internal and external distractions, and single-tasking for higher quality work done faster.


shopify-author Gregory Ciotti

 

Gregory Ciotti

www.sparringmind.com

 

To better spend your time, start by understanding where your time is spent. There are great tools out there to track time, but in all honesty, I prefer to keep it lightweight—Marc Andreessen’s notecard system has always worked for me.

If you haven’t come across it before, it involves a simple 3×5 notecard, which you use to keep track of your main to-do’s from the day. On the back of the card, you’re supposed to write things you got done that you didn’t initially plan to get done the night before—the workday always likes to sneak in plenty of extras.

By looking at your 3×5 card at the end of the day, you’ll see what you prioritized (and if you got it done) and what work was added to your plate. Extra work is fine, but if you’re not clearing off your main tasks day-after-day, something is wrong. That’s my simple litmus test.


shopify-author Ann Gomez

 

Ann Gomez

www.clearconceptinc.ca

 

Focus.

Focus. Far too many people are tying to tackle too many things at once and as a result, they make very little progress (and end up burning themselves out in the process). Consider what your top impact activities are and build your day around them. Don’t let other distractions and enticing opportunities dictate your day.

You also likely need a solid priority management system to help manage your priorities. We like to call this your “Master Plan”. This is where you list your immediate priorities and all the associated tasks. You can also list your “someday, maybe” goals on your Master Plan, but you should be clear that you do not have time to focus on these until your current priorities are achieved.


shopify-author Ari Meisel

 

Ari Meisel

www.lessdoing.com

 

Hire a virtual assistant and outsource everything you shouldn’t be doing yourself.

Ari Meisel quote graphic


shopify-author Carson Tate

 

Carson Tate

www.carsontate.com

 

As an entrepreneur, you’re in over-performance mode a lot of time because you’re all in. Pace yourself. There will be time. You’ll need the time, energy, and attention though; and when you go full throttle right out of the gate, you’ll exhaust yourself. Do you know what good enough is for each of the projects on your list? This is good enough for the organization and good enough for you. Overthinking, over editing and over tweaking wastes valuable time and is not necessary. Do good work, and then stop.


shopify-author Rodolphe Dutel

 

Rodolphe Dutel

www.remotive.io

 

Manage your cognitive load.

Manage your cognitive load so that you don’t have to “keep remembering things”. To do that, I use SaneBox to reduce my email load, then I document everything I sense is important in Evernote. I run 35 separate Evernote Docs with notes on chats with people I regularly work with on anything important (questions, results and action items). All tasks then feeds in a centralized To Do list I can prioritize and assign to my calendar (currently Sunrise).


shopify-author Peter Bregman

 

Peter Bregman

www.peterbregman.com

 

The most important thing a busy entrepreneur can do is to stop everything and think. As a busy entrepreneur myself, I know how easy it is to move rapidly from one thing to the next, without even a pause for breath. But that’s a mistake.

Take at least 5 minutes in the morning to think about your day.

  • What’s most important for you to accomplish today?
  • Does your calendar reflect that priority?

Set your phone to beep every hour and, when it does, ask yourself:

  • Am I doing what I most need to be doing?
  • Am I being who I most want to be?

And at the end of the day, Pause for 5 minutes and ask yourself:

  • What did I learn? Anyone I need to thank or acknowledge?
  • Anything I want to do differently tomorrow?

So often, we think of time management as increasing our efficiency. But some of the most efficient people I know are ineffective. The key is to be effective – to work on what’s most important and to leave everything else out. That takes forethought, planning, and hour-by-hour execution.


shopify-author Jocelyn K. Glei

 

Jocelyn K. Glei

www.jkglei.com

 

My advice is to build 2-4 hours of unstructured time into your weekly schedule. This is time set aside with no agenda beyond learning, exploring, and thinking. For many busy entrepreneurs this might seem counter-intuitive or just plain unrealistic. However, research backs up the importance of having “slack” time in your schedule on two fronts:

1. When you’re constantly busy and have no free time—as in every minute of every day is scheduled back to back—you max out your brain’s bandwidth: your cognitive abilities decline, you become more prone to making errors, and you’re less insightful.

2. Early on at Amazon, Jeff Bezos left his Mondays and Thursdays completely unstructured so that he always had time to devote to thinking deeply about the vision of the company. Making some “unstructured time” sacred is a hallmark of successful CEOs because without it they will always be reacting to the problems others are putting in front of them, and never proactively thinking about the future of the company.


shopify-author Stever Robbins

 

Stever Robbins

www.steverrobbins.com

 

Divorce your computer!

Divorce your computer! Seriously. If you’re the driving force behind a business, there’s very little you do on computer that’s the best use of your time. Twenty years ago, computers were productivity tools. Now, they’re distraction tools that kill focus, kill creativity, and kill our ability to do good conceptual thinking by providing a never-ending stream of irrelevant interruptions.

  • Physically arrange your workspace around a blank desk, not around your screen. When a computer task crosses your mind, add it to a paper “computer to do” list that you keep handy. At defined, scheduled times of day, walk over to your computer and go through your computer to-do list. Treat the computer as a tool that you use consciously, take out, and put back. Don’t use it as a default location to distract your mind and attention.
  • Put your laptop away during meetings. Take notes by hand. You’ll connect better with people at the meeting, and you’ll have far better recall for what happened.
  • Use a paper to-do list for each day’s top 3 priorities. Keep it in front of you at all times. Endless electronic to-do lists allow items to get trapped “below the fold” and fall off your radar screen. Reviewing your endless to-do and writing down today’s top priorities forces you to think strategically about which things you choose to do.
  • Don’t triage your own email. Have your assistant do that, and bring only the most important items to your attention.
  • Respond to email with a single sentence. If more is required, dictate the bullet points to your assistant and have them compose reply emails on your behalf. You just review and send.

shopify-author Kamil Rudnicki

 

Kamil Rudnicki

www.timecamp.com

 

Take your time to do right things.

Take your time to do right things. Everybody wastes time, so focus on being effective – doing right things, instead of being efficient—doing things well. Working in constant pressure is not ok. Feeling anxious and overwhelmed is not ok. Do you regret making decision? Stop.

You shouldn’t judge your success based on outcomes by themselves. The most positive results can be from things that you don’t have to do. Make the most important things in the morning—studies shown that after using your willpower later in a day people starting to make bad decisions.


shopify-author Katy Whitton

 

Katy Whitton

www.flippingheck.com

 

Having worked with a few start-ups in my time, as well as running my own business, I think that finding a stable time management technique that works for you is key to being able to get things done.

There are so many new tools that come out each month (week even!) that promise to be the ultimate organisational product but the problem is that the time and energy we invest in setting up and getting to grips with these new systems are actually taking us away from being productive.

Our tendency to latch on to the next new “shiny” thing that comes along because we think it will solve everything can upset a pre-existing and well thought-out workflow and actually harm productivity in the long run.

I’ve gone from paper to PDA to paper to Phone and back to paper again because some new app or system caught my eye rather than sticking with what was working for me. When I think of the lost hours moving my lists from paper to app to paper to app it makes me shudder!

TLDR: If you’re happy with your existing system remember the addage “If it ain’t broke don’t try to fix it” and if a new technique comes along that really excites you, figure out what has peaked your interest and try and incorporate that element into your existing system before scrapping everything and starting over.


shopify-author Tor Refsland

 

Tor Refsland

www.timemanagementchef.com

 

I prioritize my tasks using the ABCDE method:

A: Tasks you must do – serious consequences if they don´t get done

B: Tasks you should do – mild consequences if they don´t get done

C: Tasks you could do – no consequences if they don´t get done

D: Tasks you delegate

E: Tasks you never do

Here´s the trick: you never do a B task before you have done all the A tasks, and you never do a C task before you have done all the B tasks. Then apply the 80/20 rule to identify each day; which 20% of the tasks on your to do list will give you 80 % of the results.

You might be thinking, “Tor that sounds cool and all that. But does that really help you become more productive?” Good question! Judge for yourself… I applied this when I spent 20 hours creating the roundup post 80 Productivity Tips From Incredibly Busy Experts that generated 20,231 page views in 6 days. The post has now 1700+ shares and 98 comments. If I hadn´t been very productive, I would have at least spent 40-50 hours to put together such a post.


shopify-author Tim Bourquin

 

Tim Bourquin

www.afteroffers.com

 

If it doesn’t get scheduled it doesn’t get done!

For me, if it doesn’t get scheduled it doesn’t get done! So scheduling every hour of my work day is critical to staying focused and productive. Even “free time” to pursue side interests is put on the calendar.

Time management is all about accomplishing specific tasks each day, and the only way I know how to accomplish goals is to break them down into very small projects that I can achieve on a daily basis. Every day on my calendar gets one small piece of the larger goal and when I accomplish that I’m done for the day.

I also schedule a specific time of the day to work on things. If I don’t schedule that time and block it out on my calendar, it doesn’t happen. Each step should take no longer than one hour per day to accomplish. If I find it’s going to take longer than an hour to do that step, I haven’t broken it down enough.

Even if I finish that’s days steps early, I keep myself from doing the next step. I know that sounds counterintuitive, but doing so keeps me from getting burned out and I’m more motivated for the next day’s hour of work. This strategy also keeps me from getting a step “half done” which doesn’t feel as good as getting everything done that was planned for that day.

Managing my time means planning it in advance. The last 30 minutes of my day is always set aside to schedule the following work day.

It takes discipline, but it’s the only way I know to be productive.


shopify-author Monica Ricci

 

Monica Ricci

www.monicaricci.net

 

Always wait at least an hour before checking email in the morning. When you begin your day in “response mode” it’s too easy to go down a rabbit hole of answering email and before you know it, you’ve lost half the day and you haven’t addressed anything PROactively because you’ve spent your morning REacting.

Use your calendar religiously. Never rely on your memory for your appointments with others or with yourself. Relieving your brain of having to remember your schedule leaves it free to be creative, solve problems and be present in the moment with others.

Always build buffer time around appointments in your calendar, to account for travel time, preparation time, and follow-up time.


shopify-author Mike Vardy

 

Mike Vardy

www.productivityist.com

 

Don’t hyperschedule yourself. Use your calendar for big blocks of time chunks – such as daily themes or weekly project sprints during a consistent time period (i.e. writing your book from 5 am – 8 am every weekday) instead of allocating every minute of the day with something specific.

Your to-do list can offer up the details because that is what is designed to do. Let your calendar act as a broader trigger that leads you to look at the details on your to do list. Then you can decide what you need and want to do on any given day with intention and attention in mind.

Mike Vardy quote graphic


shopify-author Mark Manson

 

Mark Manson

www.markmanson.net

 

My high school math teacher once told me that if you’re stuck on a problem, start writing down numbers and you’ll be amazed how often you figure out the solution as you write. I’ve found this true in all of life, not just math.

Whenever I get stuck on something, don’t know how to start a project, get anxious or start procrastinating, I force myself to do the simplest and smallest part of the task. I lower my expectations from completing the whole project to doing the simplest, most achievable component—I’ll write the first sentence, put in the first line of code, create the first line in the spreadsheet. It sounds so simple, but when you do this, you discover that action is not only the result of motivation, but rather the cause.

And what invariably happens is that you finish that first thing and it spills into the next, and then the next, and like a snowball, hours later you’re charging miles downhill and you don’t even remember why it was hard to start out in the first place.


shopify-author Peggy Duncan

 

Peggy Duncan

www.personalproductivityexpert.com

 

People often choose working harder over taking the time to figure out how to work smarter. Entrepreneurs can actually create more free time by examining their processes more closely.

First decide if the work is necessary. If it is and you have to do it more than three times, you’ll need to develop a process that is well-thought-out, includes everyone who touches it, and is documented so anyone can follow it. Once you figure out the best way to proceed, choose the right technology to get it done.


shopify-author Donald Latumahina

 

Donald Latumahina

www.lifeoptimizer.org

 

Apply the 80/20 rule.

Apply the 80/20 rule and eliminate your least productive activities. Doing this allows you to be productive without being busy. But first you need to have clarity regarding your priorities and the willingness to let go of some opportunities.


shopify-author Brian Tracy

 

Brian Tracy

www.briantracy.com

 

Start your day earlier than everyone else. If you read the biographies and autobiographies of successful men and women, almost all of them have one thing in common and that is the habit of going to bed at a reasonable hour and rising early. By waking before the rest of the world, you have time to plan your day in advance and get a head start on some tasks that may be looming over your head before others are awake to interrupt you.


shopify-author Rosemary Rice

 

Rosemary Rice

www.dailyplanit.com

 

Be aware of how your time is really being used, and to choose tasks that provide the highest value with the lowest use of resources as high priority once urgent matters have been dealt with. It may sound boring and tedious, but a time audit can reveal surprising information about time use and lead to positive change. There are some easy ways to accomplish a time audit, like using color codes for different activities to color in a chronodex.


shopify-author Michael Sliwinski

 

Michael Sliwinski

www.sliwinski.com

 

My top management tip for busy entrepreneurs is the “Pomodoro Technique” and “Unschedule Calendar“. This basically means I just put a timer for 25 minutes and start doing only one task. This time pressure and single focus helps me get back on track and get into my productivity rhythm. On bad days I spend most of my days like this.


shopify-author Chris Bailey

 

Chris Bailey

www.alifeofproductivity.com

 

At the start of the day, ask yourself: by the time the day is done, what three things will you want to have accomplished? It’s a simple tactic—almost stupidly so—but hardly anything else will help you work more intentionally.

Chris Bailey quote graphic

The tactic does a few things at once: it helps you filter out what you shouldn’t be spending time on every day from what’s actually important; it gives you a guiding light for what’s important for when shit inevitably hits the fan; and it helps you consider your limits every day—if you have a lot of meetings on a given day, as an example, you’ll have less freedom to define what you need to get done. Plus, it only takes a minute!


shopify-author Helen Segura

 

Helene Segura

www.helenesegura.com

 

At the end of each day, map out which tasks need to get done the next day and how long each one will take. Then schedule those tasks onto your calendar in between the appointments that are already on there. Time management is all about mind management. Once you realize that you’re in control of your clock and can tell your time what to do, your work life and personal life will become less stressed.


shopify-author Dave Seah

 

Dave Seah

www.davidseah.com

 

My personal time management tip is to freely allocate the time you need to realistically do a piece of work to the minimum next stage of completion.

By “realistic”, I mean the actual amount of time it would take, not the amount of time you WISH it would take. Once you have made that decision, then don’t think about time at all and do the work. Thinking about time management is the biggest waste of time I indulge in, ironically! While I am worrying about how long something takes, I am not using 100% of my attention on doing useful work or solving problems. As a solo entrepreneur, I have to be careful about avoiding unproductive management mindsets that focus on time efficiency. Many problems do not have ready answers, requiring research or trial-and-error with time requirements that can not be predicted. The best you can do in those cases is allocate blocks of time in chunks to work on the problem without worrying about it, trusting that a solution is on the way. I think that entrepreneurs who are used to working with computers are often frustrated by the realities of dealing with markets and suppliers with all the vagaries they have, so it’s really important for me to accept the reality of the uncertainty of time, and not fret about it.

By “minimum next stage of completion”, I mean a “useful element” that contributes to your working goals in some salient way. I tend to fixate on the “end result” instead of the next stage because I am impatient, but this just creates frustration that again burns up energy that might otherwise be used to make something.

Giving myself enough time to get something done, and also giving myself the permission to not feel rushed or guilty about the time it takes is what works for me. That said, I am not a competitive market-driven entrepreneur that is trying to beat everyone else to market; the goal of my entrepreneurial activities is to support my creative life, not consume it with worry.


shopify-author Josh Coffy

 

Josh Coffy

www.flightmedia.co

 

Have a productivity routine that you religiously follow daily. For example:

1. Workout – 4:30am

2. Create list of top 5 to-dos for the day – 7:00am

3. Work uninterrupted for 50 minutes, then break for 10 minutes – several times per day

4. Don’t leave the email tab open

Just like you build a strategy for everything else in your business, you absolutely must have a strategy for productivity. I workout because it makes me feel good, wakes me up and energizes me for the rest of the day.

I create a list of my top 5 to-dos for the day because if it’s a never-ending list, then it often leaves me unfulfilled and like I accomplished nothing. (Even when I do.)

I make time for several hours of 50-minute working sessions with a 10-minute break because it’s the only way I can accomplish those five to-dos.

I don’t leave the email tab open because my day goes down the drain in zero seconds flat. Make a routine, stick to it, and you’ll find time you didn’t know you had.


shopify-author Liz Summer

 

Liz Summer

www.lizsumner.com

 

When you find yourself avoiding a task it’s usually because you’re unclear about what needs to happen next. It’s usually one of 3 things—find out, decide, or do. Do you need more information, make a choice, or take an action. Look at your resistance through the find out, decide, or do lens and it’ll move you forward.


shopify-author Annie Sisk

 

Annie Sisk

www.pajamaproductivity.com

 

The biggest and best time-management tip I can offer for busy freelancers and entrepreneurs—really, for anyone—is this: Stop thinking about it as “time management.”

When we say “time management,” we’re really saying it’s the time that needs to be managed. But in 99% of the cases (a totally unscientific percentage but it’s relatively accurate in my experience), it’s not time that needs better managing—it’s us.

So instead, try thinking about it in terms of choices. An example: Imagine your absolute favorite band comes to town. Or Hamilton. Whatever. Something you really want to go to, but impossible to get into. But lo and behold, two tickets fall into your lap. No matter how busy you are, or think you are, if you’re like me and most people, you’re gonna find a way to go, right?

In other words, you’ll make a choice. Note I’m not saying going to a concert (or Hamilton, or anything generally fun) is a bad thing. I’m saying that when you really want to do something, you make that choice and you make it work. The same is true of things that aren’t so much fun but are critical – say, a sick kid that needs to get to the doctor’s office. You find a way. You choose.

So start looking at everything on your task list as a series of choices. You can choose to do them, or you can choose not to do them – to defer, delegate, or delete them. A weird thing starts happening when you look at it as a choice: you wind up making better choices, simply by realizing the power was in you all along.


shopify-author Thanh Pham

 

Thanh Pham

www.asianefficiency.com

 

Do the hardest thing first, every single morning. When you start your workday, tackle the task you find the most difficult to do or are most likely to procrastinate on. When we postpone those kind of tasks till later in the day, we often get stressed about them and keep postponing them.

Thanh Pham quote graphic

By flipping it, you can go on with the rest of the day knowing you were productive. Even if you did nothing else, you still had a productive day. I’ve done this for the last 5 years of running my business and it helped us tremendously. Everyone in our company does it too and it’s part of our onboarding training to teach people this concept.


shopify-author Christiaan Riemens

 

Christiaan Riemens

www.improve-hq.com

 

Prioritize!

Prioritize! Emails keep piling up, phone calls keep coming in, there are tons of to-do’s: an entrepreneur’s workload is enormous. Prioritizing that work is key to staying focused. The more you’re able to prioritize, the more efficient you’ll be. This is where Eisenhower’s urgency-importance matrix comes in, forcing you to think twice before adding a task to your to-do list.

Here’s the how. Select those tasks that are most urgent. Ask yourself: are these equally as important? Postpone what is less urgent, delegate what is less important. And if it’s none of the above: get rid of that to-do.


shopify-author Allyson Lewis

 

Allyson Lewis

www.the7minutelife.com

 

I have seven tips.

1. De-clutter your brain. You feel stressed because you have too many unfinished tasks. On a plain piece of paper, write them ALL down. Then cross out any that are not absolutely essential. Be brutal. You don’t have to do everything, you only think you do.

2. Conquer the unfinished task. Looking at your list, commit to completing one task a day until the list is complete. Revisit this list often! Things that seem essential today may not look that way next week.

3. De-clutter your world. A desk or kitchen counter covered with papers and other clutter also makes you feel more stressed than you need to be. Stop, take a deep breath, and take a few hours to either toss it, file it, or take care of it. Start with your top priority work or home space and go down the list, doing a little every day, one day a week, or whatever set schedule works for you.

4. Limit or block distractions. Shut off any email, Facebook, or Twitter alerts each morning until your most important tasks are complete. Research has shown that it can take as much as 25 minutes for you to mentally reenter a task after an interruption. Instead of jumping to respond to these interruptions, process all of those communications in scheduled blocks.

5. Act with purpose. When was the last time you actually wrote down your purpose in life, or your top priorities? What is the one thing most important to you in life? What are the priorities that further that purpose? Write them down. You will be amazed how this helps clarify what you need to do each day (and what you don’t).

6. Set goals. Yeah yeah, you say you know what your goals are. But have you written them down? Neuroscience has proven that the simple act of writing actually tricks your brain into achieving more. What do you want to achieve this week? Month? Next 90 days?

7. Make your “5 Before 11”. Make a list of five things you can commit to doing before 11am tomorrow morning. Does each task move the needle forward on your purpose, priorities, and goals? It should. When you do your 5 Before 11 tomorrow, you will have a blissfully peaceful sense of accomplishment, knowing you have done what is meaningful to you. After 11am, you can add whatever you want – knocking out an unfinished task that does not relate to your priorities, taking an unexpected meeting, doing something spontaneous with your kids or husband. You actually have some freedom and flexibility now.


shopify-author Shane Parrish

 

Shane Parrish

www.farnamstreetblog.com

 

This is somewhat counter-intuitive … the best way to gain time is to make better initial decisions. We spend so much of our time and energy correcting mistakes and scrambling out of bad situations. If you can reduce folly on your initial decisions, you’d have a lot more free time. One way to improve the quality of your decisions is to clear your mornings and think for 30 minutes alone about the problem before making a decision. Try not to make big decisions in the afternoon or later in the day.


Have a great time management tip of your own? Share it comments!