Plan Your Future

Resources to help you plan the life and future of your dreams

You’re in the right place if…

  • You know where you ultimately want to be, but have no clue how to get there
  • You feel like you’re always busy, but never making progress
  • You need specific actions to help you get to where you want to go
  • You’re not currently tracking your progress and thus not sure what’s working and what’s not
  • You’ve never found success sticking with and following your goals



The Roadmap is an original Ways & Meaning resource that was created particularly for solopreneurs and small business owners looking for a SIMPLE and EASY to use system for keeping track of their businesses, projects, and just life in general.

Start here to plan your future and build the life of your dreams!

What the hell does it mean to plan your future?

It's about seeing a path to your dreams

Planning has a bad reputation in the world of entrepreneurship. The common advice you hear is to move quickly and fail often. Don’t think, just do. Get your product out to market, listen to the feedback, tweak it, improve it, rinse and repeat.

This is TERRIFYING advice to a control freak (me). And most people who suffer from any sort of self-confidence insecurity that causes anxiety, fear and risk aversion in general.

But don’t worry, because there are really two types of planning. And although one can be harmful, the other can be extremely beneficial, if not completely necessary. 

Planning at its best is all about discovering hope to achieve your dreams. In other words, planning is about:

  1. setting realistic goals (I know where I want to go)
  2. figuring out how to achieve those goals, including the ability to stay flexible and adapting to alternative routes (I know how to get there and can tolerate change along the way), and
  3. believing in yourself (I can do this!)

A LITTLE bit of planning can go a LONG way. Understanding your basic strategy before jumping in can help make the whole entire process a LOT easier.

Planning at its worst is trying to figure out all the millions of things you need to do along the way, when and how, before you even start. This is over-planning. And this will kill your venture before it ever begins.

Why is it so important?

Planning reduces anxiety and increases hope

Nothing ever goes as planned. Have you even known of anything–a business, a project, a renovation–going as planned? No. Because it never (or rarely) happens. So then why do we do it?

Most people plan to reduce risk, uncertainty, and ultimately fear and anxiety. It helps to calm our mind that what we’re trying to do IS possible. That we’ve considered many of the challenges we’ll face and we know of ways to overcome them. We’re prepared, we’re ready.

Planning is a form of control (or perceived control) over a situation. Once there is a basic plan in place, once we can see a path to our dreams, the moment we build a sense of belief in ourselves that we can do this, a seed is planted. That seed needs constant nurturing, care and compassion, but that seed will eventually blossom into our courageous spirit of self confidence that is needed to see out our dreams to the end. 

Planning gives us hope. For myself and many others, planning is the first step towards realizing our dreams

So how do I do it?

Plan just enough to believe in yourself

The biggest pitfall when it comes to planning (especially for entrepreneurs) is OVER planning. This is particularly true if you’re leaping out of the corporate world where a detailed plan, proposal or strategy is the required first step before launching any new project or initiative.

If you consider yourself Type A, a control freak, a perfectionist or any other left brain dominate personality type, this might be an even bigger pill to swallow. I know, I’m part of this group. Over-planning is a defensive mechanism against failure. Of course the fallacy in this approach is that we plan, and plan, and plan, further procrastinating our dreams. Then we feel guilty, then we give up. We fail either way.

The greatest single gift you can give yourself if you want to be a successful entrepreneur is to learn how to plan just enough to get going. Plan enough to see a path to success, plan enough to reduce your anxiety to a manageable level, plan enough to get past your minimum risk tolerance threshold, plan enough to build belief in yourself. 

According to Oprah, “Before you embark on any quest, you must first articulate your vision…and most important, you must believe with your whole heart that you are capable of achieving your goal.” Planning can help you do this.

So what does ‘enough’ look like? It’s different for everybody, but for me it looks something like this..,

STEP 1: Know where you're trying to get to

Regardless of whether you’re trying to plan out your entire life, your new business, or just your next project, find clarity of purpose first. In other words, what is your #1 priority or focus?

Luckily for all of you, I’m in the process of developing a new course, Find Your Way, that will guide you through the process. It’s designed to be re-visited often and you’ll have access for life so that as you discover more about yourself, and what matters most to you, you can update and improve the clarity and definition of your own life’s purpose.

But if I’m going to be honest, I don’t want you to wait. I want you to start figuring this out TODAY. So here are some additional resources to help you get started.

STEP 2: Figure out the best path to get there

This is often the fun part of planning. This is where strategy comes in. There are often many paths to the ultimate destination we’re trying to get to. Once you know where you’re going, you have to consider which is the BEST path, for you.

For some people that might be the path of least resistance (me). For others it’s the one that appears most exciting, adventurous, even challenging. Or maybe it’s the cheapest, the fastest, the least risky. 

But how do you choose? Think about what you have (your skills, available time, money, interests, etc.) and what you need to successfully follow each option.

You don’t need to limit yourself on what you don’t have, but you do have to consider if you’re willing to spend the time, money and energy to acquire those things. 

Need an example? I wrote out this blog to walk you through how I figured out the best business model for my new business. You can read it here.

STEP 3: Plot out the major milestones

As a means to counter against the urge to over-plan, I recommend focusing only on the major phases of your project at the beginning. This is where restraint is welcome in the world of entrepreneurship. 

The purpose of this exercise is to determine the ORDER in which things must happen by considering which are truly RELIANT on each other.

It is optimal to focus on one thing at a time. Often this is not possible, especially if you’re relying on other people, contractors or employees to assist with parts of what you’re doing. But whenever possible, focus on the most important task at hand, and nothing else. 

And this point you’ll also want to assign rough time estimates for each milestone. Double however much time you expect it to take and then don’t be surprised when you go over your limit. Keep in mind how much time you have available for this work (i.e. can you work during your normal work hours? Is this something that has to be completed on nights and weekends?) and black out any days/weeks when you know you’ll be busy, when you’re on holiday, when you have another big deadline approaching, when you know the kids will be out of school, etc. Be realistic. Being over-ambitious will set you up for failure and will injure your confidence in yourself that you can actually accomplish this.

Here’s what this looked like for me in setting up Ways & Meaning (keep in mind I only had about 10 hrs / week for this)

  1. Understand the purpose of what I wanted to do and why | 1 year of ‘thinking’ while working on my old consulting business
  2. Research and choose a business model that fit my needs | 3 months
  3. Market research to better understand what was available, who my ideal customer was, what their needs are, and then develop my brand | 2 months
  4. Begin building my customer base through my newsletter (you can sign up here, it’s awesome!) | ongoing
  5. Build the website with minimum viable content to launch | 4 months
  6. Launch the business | 1 month
  7. Create and curate free content | ongoing
  8. Create first paid course and establish new product launch plan moving forward | 3 months – HA! 1 year later I’m still working on this (speaking of going over your limits!)
  9. Focus on SEO and guest blogging to send traffic to the website | 6 months
  10. Implement affiliate program for all resources and link recommendations | 1 month for implementation / ongoing

I’m currently about half way through this list. I may be an expert at purpose, strategy and planning, but I’m not an expert on operating a successful blog/digital product business, so if you are, and if you have any recommendations on my plan, please let me know:

STEP 4: Determine what success looks like

This is all about establishing goals, but a better way to think about it, is to envision what success looks like at each major milestone, and at your ultimate purpose as well. 

In the interest of being transparent and sharing my journey, this is how I define success for my business at every step of the way (numbers corresponding to the milestones listed above):

  1. Earn $50-75k / year working 25-30 hrs per week, spending a majority of my time (at least 65%+) researching, writing and creating on the topics of entrepreneurship and mindfulness in a way that improves the lives of those I reach
  2. Success for this milestone is to complete the task, but you can read this blog which goes more into the results of determining a business model that fits your lifestyle
  3. Have a BASIC understanding of what’s available, begin following 5-10 competitors to monitor what they do, write up an ‘ideal customer’ description, complete my brand and style guide
  4. Send valuable emails to my list minimum twice monthly (with an average open rate over 35%); build the list to 350-500 by website launch and to 1,000 by the launch of my first course
  5. Launch website with enough articles and resources to satisfy all categories and sub-categories + minimum 3 original articles and 1 original resource
  6. Launch my website at least 12 weeks before baby #2 is due
  7. Post 1 original blog per week (and up to 3 curated articles), add 1-3 resources per week (mix of original and curated)
  8. Complete course prior to baby #2 arriving, but launch 6 weeks after leaving time to market and plan launch strategy; earn minimum $5,000 in first year from course sales
  9. Reach 1,000 viewers per month by end of 2019, ramping up to 10,000/month by end of 2020
  10. 10% of revenue from affiliate programs by year 1, ramping up to 50% over 3 years
Just to be clear, sharing these goals with you is TERRIFYING for me. I have a very strong sense of belief in myself that I will eventually make this all work, but I’d be happy if I achieved 60% of these goals. I don’t want anyone thinking this was easy. But Brene Brown is teaching me to be a bit more vulnerable and studies show that sharing your goals with other people help to keep you accountable, thus improving your odds at success. So here we are 🙂
Also you might notice that I haven’t stuck to any particular format or common approach like SMART goals. When you’re the only one reviewing your progress….keep it simple and do what works for you. It’s one of the benefits of being your own boss.
It also might look like there are a LOT of goals I need to be tracking…but remember, the point of this is to focus on one thing at a time. That also means I’m focusing on one goal at a time.
I do keep a strategy tab in my spreadsheet that I’ll share [coming soon!] so that I know what I’ve done, what I’m doing, and what’s up next. But the point of even that document is to allow my mind the time and space to focus on one thing at a time (knowing that everything else is captured somewhere for later reference).
I’ll be sure to follow up with you in a year (and every year thereafter) to let you know how I’m doing, what worked, what didn’t, and how I’m adjusting and moving forward.

STEP 5: Stay focused on your progress

Setting goals and establishing a plan is important because it allows you to then track your progress. Studies show that we receive more joy from the progress we make towards our goals, then we do actually achieving them. 

This is because our brains get small releases of dopamine everytime we make progress towards a goal. But our brain also adjusts back to normal quite quickly, even when we achieve the really big milestones. So if you only have 1 or 2  giant and difficult to attain goals, you’ll only feel that pleasure once or twice (assuming you actually achieve what you set out to do). 

But, if instead, you focus on all the little milestones along the way, you can continuously invite your brain to reward you, resulting in a happier brain, a more satisfied you, and a more accomplished to do list.

So the lesson here is once you see the big picture, you can start breaking things down into smaller, more manageable chunks. Don’t try to put everything on your to do list at once. This will just waste time, stress you out, and likely give you a panic attack. 

Just focus on the small chunk you’re working on and get it done. Then move on to the next. 

Staying focused can be REALLY difficult, especially when there are so many fun and shiny distractions to waste time on–researching anything and everything on Google, finding brand inspiration on Pinterest, reading inspirational books and articles and on and on and on.

There are a ton of tips, hacks and ideas out there for how best to manage your to dos and stay focused. But at the end of the day you just gotta do whatever works for you.

What works for me is to have a two part system, which you can read all about in this article I wrote on effective to do lists:

  1. a large roadmap by week or month (depending on the size of the project) that plots out the major milestones
  2. a separate ‘current to do’ list that includes all the small details I need to accomplish for the current milestone with due dates and notes.

At the top of the ‘current to do’ list I write out and highlight (in black background with white font) my #1 focus or priority, followed by other priorities that are less important. I allocate a percentage of my time I should be spending on each priority each week, ensuring that the #1 focus should have a minimum of 65% of your time allocated (up to 90% is the goal). I don’t bother actually tracking time, but I do work out how many hours I have for each priority each week and I try to stay mindful of sticking to that.

This system works for me. It helps when I find myself off track or being distracted, or when I need to decide whether to do X or Y today (or which to do first). All I have to do is remember what I promised myself I would do and then hold myself accountable. It’s a black and white way to make decisions as I go.

If an idea or thought comes up about some other milestone, task or chunk of work I shouldn’t be working on, I add a note in my roadmap so that I don’t loose it, then go back to the task at hand.

The bottom line is, if you commit to nothing, you’ll be distracted by everything, so don’t do that. Instead here are some of my other favorites tips, tricks and hacks to help you stay focused on the task at hand


Before you know it, you’ll be up and running, your plan will be collecting digital dust on your computer, you’ll have built the confidence you needed to move forward and learned enough to improve with each and every step.

Congratulations. You did it!

Now what? Eventually you might decide you want more. But how much more? How do you know when enough is enough? How do you know when to stop moving and just enjoy what you have? Let’s explore this next…

Popular Resources TO PLAN YOUR FUTURE

The Roadmap is the best free project management tool to help client and content based small...
A simple to use to do list template with a very special feature! This template includes...
An exercise to describe, design, challenge, and pivot your business model.

Popular Articles TO PLAN YOUR FUTURE

How I keep an effective to do list

Keeping track of your tasks likely either makes you feel completely overwhelmed and anxious, or totally productive and on it, or a combination of both. If you’re the former, it may be that you just have a bad system (or a serious lack of focus). Either way, hopefully this article can help you get your to do list back under control and make you feel like a boss killing it every day.

The best free project management tool for content and client based businesses

The Roadmap is the best free project management tool to help client and content based small business owners organize EVERYTHING.

On Fear and Confidence

There is one thing I know for sure about being an entrepreneur (or following any dream for that matter). The difference between success and failure lies in your ability to overcome fear. Everybody fails. Those with the greatest success, often failed the most. Albert Einstein failed his first entrance exam to university. Steve Jobs was famously fired from Apple before being re-hired and inventing the iPod and iPhone, changing everyone’s lives forever. Oprah Winfrey was fired from her first broadcast journalism job after just 6 months. Lady Gaga was cut from her first label. We all fail. It’s a necessary part of the journey. So why does it breed so much fear in us? And more importantly, how the hell can we move on from it? I wanted to launch this new business with an article that epitomized my journey to get here, to realize this dream of mine. And when I thought about what that story might be, I kept coming back to the biggest battle I’ve ever fought in my life: the war on fear.

Mindful Entrepreneurship

Ways & Meaning is a website designed for mindful entrepreneurs. But what does that mean anyway? And why does it matter? Well let me tell you, mindful entrepreneurship is the act of being intentional about following your dreams. This article is the ultimate guide to understanding this definition, the characteristics of what makes a mindful entrepreneur and the benefits of choosing this path for your business or venture.

3 Reasons you aren’t doing what you say you will do

In this TEDx video by cognitive psychologist Dr. Amanda Crowell you'll learn how to move beyond mindset-driven defensive failure and into productive failure to succeed at the problems you struggle with the most. She argues that we get trapped in the same cycles, over and over (sound familiar), and offers advice on how to break those cycles and finally succeed at whatever it is you're trying to do.

How thinking about the future can make life more meaningful

As a strategy consultant, I think about the future A LOT (probably too much). But this article helped me to justify my behaviors. Written by a Ph.D researcher for Greater Good Magazine, it chronicles the research on 'prospectus' or how thinking about the future can help us make better decisions, achieve our goals, fight off negative mental health states and just generally become more kind and generous people. Find out how and why.

Ready for the next Step?