The Expected (And Unexpected) Realities of Changing Careers

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Note: This week Foundr decided to do something a little different with our blog post. We decided to put our money where our mouth is and shine the spotlight on our CEO Nathan Chan. So we go back to the origin story, the trials, and the lessons learnt, to give you some insight on what it’s like when it comes to changing careers from full-time employee to full-time entrepreneur.

What is it that motivates people to leave the corporate world to start their own business?

It could be that desire to create something new, to fulfill that lifelong passion of yours. Or maybe your boss just sucks and you know you can’t go back after you’ve left a nice, hot, steaming present on their doorstep.



We’ve all worked a job we’ve considered a dead-end before. But the pattern of a steady paycheck, good friends, and the security of routine kept us in a place we know we didn’t love.

It’s not like you don’t like it, or that it’s not comfortable, you just don’t love it.

It’s like that feeling of going to the movies with your friends to see the latest Adam Sandler movie. You know you’re not going to love it but all your friends are going, and it’s a decent-enough film. So you sit through it and watch the same routine of jokes over and over again. Sure you get a chuckle here and there, but generally it feels more draining than anything else.

Now imagine feeling like that for the rest of your life.

And yes I did equate working in the corporate world to watching an endless marathon of Adam Sandler movies.

Entrepreneur fail does an excellent job of showcasing the crossroads we often find ourselves in.

#entrepreneurfail Road Less Taken

You’re not the only one that feels the uncertainty of leaving a stable job to become an entrepreneur. After all being an entrepreneur carries its own set of challenges and hardships. It’s only reasonable to feel unsure.

At the time of this publishing it’s been just a little over a year since Nathan Chan left his job to work on Foundr Magazine full-time.

Here he is on his last day at Intrepid Travel.


Like the majority of people the decision didn’t come easily and the transition was hard. There were highs and there were lows, but today Foundr Magazine is one of the top 10 business magazines in the app store.

Here’s how Nathan made the move from a full-time job to full-time entrepreneur. The risks he took, the lessons he learned, and the strategies to ensure success.


Find the motivation

“I think one the biggest things you need to be is hungry. If you’re not hungry, if you’re just doing it for fun, if you’re just doing it because you want to see what happens, if you don’t want it bad enough, if you’re doing it half-assed, if you’re not really trying to give it 100%, then you’re not going to make it.

I think you have to want it so badly, you have to have so much drive and determination. And you have to be prepared to get up at 5am in the morning when you’re super tired and you’ve gone to bed at 1am. You have to be prepared to write a whole ton of emails and be rejected and have people not reply back to you.

That’s the kind of stuff you have to be prepared to do because you’re going to get a lot of that.

There’s going to be a lot of people telling you that it’s not going to work, there’s going to be a lot of people that aren’t going to get back to you, there’s going to be a lot of people who won’t try to help you, there’s going to be a lot of people who want to bring you down, there’s going to be a lot of people who think you’re an idiot.

You’re going to want it so badly you don’t care about what people think, you’re not afraid to fail. You’re super hungry.”

First of all, be honest with yourself. Why do you really want to start your own business?

Are you feeling like you’re not in a position to advance? Do you just not like your current colleagues? Do you want the freedom to be your own boss? Everyone’s motivation is different so don’t stress about having the right reason, just make sure you have one that’s right to you.

Because later on when the going gets tough and you feel like giving up, you’re going to need to remember the reason why you started.

Like Matthew Michaelwicz says, “See the end from the beginning.”

Keep in mind that you shouldn’t expect to achieve your goal right away. Our minds often only see the end outcome, not the work it takes to get there.

For Nathan, the IT tech support at Intrepid Travel, it was all about the lifestyle.

“Originally it was all about the lifestyle, being able to wake up when you want, being able to work your own hours, having the freedom to work on a laptop, to travel around the world, and creating something with your own two hands. I think I craved making a difference, making a dent, making an impact.”

As I’m sure many of you can relate to, it was the realization that he was working a 9-5 that wasn’t making him happy, it wasn’t fulfilling, and it wasn’t something he wanted to do.

“I was doing work that didn’t really fulfill me and I got sick and tired of doing work that I didn’t enjoy.”

If there wasn’t a job opportunity for him to live the lifestyle he wanted, then he’d just have to create his dream job. Simple as that.


All in the preparation

So you’ve made the decision to start your own business but how do you work on your business when you have a full-time job?

A lot of people get turned off the idea of starting their own business because they believe it’s a binary decision. You have to choose between working full-time at a job, or working full-time on your startup.

But it doesn’t have to be like that.

There are too many stories of entrepreneurs suddenly quitting their day jobs in order to pursue their startup idea. Then it all sinks because they haven’t even validated their idea yet, they’ve underestimated the amount of resources needed.

As I’ve mentioned before in a previous article it’s not that entrepreneurs don’t take risks. They just don’t take unnecessary ones.

When changing careers think about using the “Tarzan technique”, as described by Derek Sivers. Notice how Tarzan swings through the jungle, he doesn’t let go of the previous vine until the next vine is supporting his weight.

While there is a certain romantic idea of jumping off a cliff and building a plane on the way down, I prefer knowing that I have a parachute if I need it.

For Nathan, he worked on Foundr on the side for over a year before finally leaving his job at Intrepid Travel.

Every day Nathan would spend at least 30 minutes to several hours working on developing Foundr. He knew that every day had to be spent moving the needle forward, even if it wasn’t much, as long as he was moving forward.

So using Matthew Michaelwicz’s goal pyramid, he broke down the goals he needed to achieve in order to make Foundr.

“I didn’t write a business plan, but I did write down some goals. Monetary goals around how much money I needed to make, how much the business had to be turning over for me to leave my job. That was really key and critical because I actually looked at those goals every single day. And I still look at those goals and I think about them, and I talk about them, and I obsess about them every single day.”

If he was going to dedicate his full attention to developing Foundr there were three things he needed to make sure of:

  • “The business was making enough to replace my income, almost,

  • I had 6 months worth of savings,

  • and I was told by my mentors and my peers ‘it was time.’”


Finding the experience

As a startup founder your ability to learn quickly and on the job determines whether or not you succeed. But it’s easy to get overwhelmed at the start, especially if it’s your first business.

No amount of books, courses, or lectures will be able to properly prepare you for the real world. At the end of the day there is no substitute for wisdom gained through experience.

Which is why it’s almost imperative that founders find themselves some good mentors.

Shortcut the learning curve and need for experience by finding someone that already has that experience.

According to the Startup Genome Report founders that have defined mentors raise, on average, 7 times more money and have 3.5 times better user growth. Almost universally mentors significantly and positively influence a business’s performance.

A great mentor has a wealth of experience to draw from, the ability to communicate openly and honestly, and be direct yet supportive.

However finding someone to call a mentor is admittedly tricky.

When it came to reaching out to Ed Dale and Matthew Michaelwicz it was all about serving first and asking later.

Here are the 6 rules Nathan stands by when it comes to finding a mentor.

  1. “Having something to show, a product / service I created that showed I was serious about building a business
  2. Serving first and ask later
  3. Showing extreme amounts of enthusiasm
  4. Not asking that person to be my mentor
  5. Being persistent when asking for help
  6. Making myself vulnerable, and simply asking for help”

Like any business or relationship it’s all about ensuring that you’re providing value, and not simply extracting it.

Ed Dale wouldn’t be someone Nathan could go to for advice if he didn’t prove that he was serious about wanting Foundr Magazine to succeed. Nathan wouldn’t have met Matthew Michaelwicz if he hadn’t offered to feature him in the earlier issues of Foundr Magazine.

In both relationships they were friends first, it was only over time they naturally became mentors. People you could turn to for advice when you need it.


The trough of sorrow

Anyone that’s ever been an entrepreneur will know this feeling.

The one where for about two weeks, maybe even a month, into working full-time on your startup you’re feeling like the very embodiment of good vibes and productivity. You’re super motivated and you’re just filled with nothing but ideas and the motivation to tackle any challenges that life might throw your way.

We call that the startup high.

It’s a great feeling. But like any other high it’ll wear off sooner or later.

The novelty of being an entrepreneur wears off and the truth hits you. That it’s all on you, if you want to succeed you’re going to have to work harder than you ever have before.

Paul Graham calls this bit the trough of sorrow.


This bit is the make-or-break point for every startup. It’s all down to whether or not you can make it through this very long and very frustrating period.

There are the usual problems to look out for. The feeling like you’re stuck in a routine, the irrational fear of failure, the demoralization.

It sucks and everyone goes through it, but here’s one you don’t expect: the drop in productivity. Which sounds weird because now that you’re quit your job to work on your startup full-time shouldn’t you be getting more done?

“One thing I didn’t expect was finding a good work routine, I remember when I first left I didn’t know what to do because I was always so used to working on Foundr after hours. So it took me a while to adjust working on Foundr full time. I remember I made a calendar of this big list of things to do and I didn’t do any of them because I was struggling to be productive.”

For months Nathan struggled with the effects of a sudden change in environment.

However like I said earlier, when the going gets tough you need to remember the reason why you started.

Cut through all the noise that’s going on in your head and remember the difference you wanted to make.

One of the worst things any founder can do is keeping everything in their head. The human mind likes to overestimate the possibility of failure, it often warps facts and blows them out of proportion. So the best thing to do is to find a system that doesn’t let those thoughts stay in your head for too long.

One of the ways Nathan broke out of the trough of sorrow was to keep his thoughts out of his head. Turning his fears into goals that he could actually see and achieve.

“I’d write my tasks for the day on post it notes, I’d write all the things that were on my mind, so I’d brain dump it all down.”

Research has shown that creating a visual representation of your problems, whether it’s a diary, a mind-map or a blog, significantly reduces stress and anxiety. That’s because when stressed your problems seem much larger than they actually are. Actually writing about it let’s you see them for what they really are: simple challenges, challenges that be overcome. Change the way you frame problems and you’ll find out that they’re not impossible, they may be difficult, but they’re not impossible.

The trough of sorrow sucks. But the key to getting through it, is to recognize and celebrate each and every victory that comes your way and to constantly seek improvement with your product/service offering.


Celebrating $5

Here is the first sale that Foundr ever made. It was $5.

Any seasoned entrepreneur will be able to tell you there’s just something special about your first ever sale. You’ll never forget your first.


As an entrepreneur the threat of burnout, depression, or simply just quitting out of frustration is always near. Which is why you must always celebrate the small wins.

In the early days of Foundr it was all about finding the small victories whenever you could.

“It might be an interview we land, or a big launch that we do, it’s just like these little wins that keep you going especially in the early days. It was more around the interviews we landed, hearing from our community members.”

Nathan always celebrated the small victories. But like anyone else, the best victory was hearing from people whose lives he had impacted with Foundr.

“For me and my own self-confidence I just needed to hear from enough of our community members that our work was appreciated, our work was helping people, and that’s when I eventually came to the realization that we were onto something.”


There really isn’t anything quite like knowing that someone took the time out of the day to tell you how much of an impact you’ve made on them.

For many entrepreneurs it’s easy to get caught up in the logistics of the business, to only think about the daily goals you need to achieve, in order to grow certain facts and figures. But the real gold is realizing that you’re making a difference, that you’re doing what you set out to do and create a change in people’s lives.

At the time of this writing we still celebrate the small victories at Foundr. Whether it’s treating ourselves to a nice lunch after the first successful launch of our Instagram Domination webinar, or planning a day for paintball for reaching our targets last month.

We make sure to keep ourselves motivated by taking the time to appreciate all the little steps it takes to building a big goal.



Changing careers can be difficult. It’s a transition period that can be at times awkward, uncomfortable, and even painful.

It’s often scary when you make the choice to leave a a steady paycheque, friends, and a familiar environment. To risk it all for a career where you’ll often stumble, hit roadblocks, and encounter setbacks.

But if we can prove that it’s possible then so can you!

There’s nothing more fulfilling and rewarding than being an entrepreneur. But as I hope our origin story shows you, it doesn’t happen over night. It took a whole lot of grit and hustle to push past it all and end up where we are today.

So learn from our mistakes, and know that a roadblock isn’t the end of the road.

As always remember to leave a comment below, and to like and share if you’ve enjoyed this article!

  • Pure gold. So nice to be able to hear a story like this from the ground up!

  • Nick Sakha

    Great article! I swear I was sitting at a Starbucks today writing goals and brainstorming on when/how/why I’m going to start my own business and leave my corporate job. This helped big time. Thank you for making a difference.

  • Esther Bwambale

    I’ve always told myself that owning my own business is not for me…but I’ve come to realise that it was just fear that kept saying that. I hope to start my own business in a two to three years and this article has been so insightful…thank you!

    • When you get out of your own head you realise you can achieve incredible things. Glad you enjoyed this article and I could send a little inspiration your way.

  • Candis

    I really enjoyed this article and I appreciate your openness about your journey to entrepreneurship.

  • Hashim

    Absolutely loved every word of this article. I honestly cannot tell you how much I can relate to so many of these scenarios that I am currently experiencing as a newly entrepreneur. The ‘trough of sorrow’ is absolutely brilliant! I had my high at launch when sales were trickling in and now I’m going through a desert-patch where I’m scratching my head thinking what to do next. Reading this article has helped me to give myself a bit of ‘slap on the face’, to refocus and to turn every vulnerability into a goal-objective! Thank you very much and I’ll definitely look forward to reading more articles! 🙂

    • Thanks so much for the lovely feedback!

      Will do my best to keep on making articles that you can keep coming back to.

  • Hashim

    Lastly as an important after-thought, I think another additional factor to consider when setting up your own business is the importance of ‘faith irrespective of what religion you follow; belief and and that relentless determination to see it through to its end-goal is ultimately what it’s all about.

    • Very true Hashim. Thank you for such valuable input, will definitely consider putting it in an upcoming article.

  • Alex

    Thanks for the great sharing, Jonathan:)

  • The merrymaker sisters

    Love this. Especially the ‘start up high’ we think we go through start up highs all the time! Then it will be like ‘oh Sh!T what the hell are we doing?!’ it’s good to know that most people really don’t know what they’re doing… we’re all just experimenting… some things work… some things don’t. But YAY for Foundr being freaking epic and doing awesome stuff! Thanks for sharing with us <3

  • Nick Boudreaux

    Great read with amazing key points that every entrepreneur can relate to from working after work to the feel of your first ever sale. Solid and useful article! Keep up the good work.

  • ukiahbeats

    Amazing! Thanks so much for sharing. Im starting a music production and teaching company and this is just what I needed.

    • Thanks for the comment and glad you enjoyed the article!

      Be sure to keep us in the loop of how you’re doing. Remember that it’s all about mindset at the end of the day, it’s not failure if it’s a valuable lesson, and it’s not success if you can’t enjoy it!

  • Jarod Guthrie

    I love this post guys! Really hits home to a lot of the struggles that we all go through as Entrepreneurs and also in life.

    • Thanks for the kind words Jarod! Glad you enjoyed it!

  • Thabiso Sebata

    My Quote of the week,

    “Spend everyday moving the needle forward, even if it isn’t much, as long as you moving forward.” – Nathan Chan

  • AnPhuong

    It’s a great sharing I’ve ever read. Hugely helpful. Thanks!

  • guilherme fellet

    Hi guys! This article is amazingly inspiring, and it´s an answer to my biggest dillema. I have my 9-5 job, and started this blog with 4 friends ( I´m from brazil, by the way…and totally dream to make it my new full-time job. Thank you for letting me know I´m not alone!

  • André Norbim

    Nice! Thanks for sharing!

  • Kristin Whitaker

    Really enjoyed the “Trough of Sorrow” graph – will definitely be keeping that in mind as I prepare to take the leap.

    • Remember that while it’ll feel like forever, you will be able to stick it out and see it through to the end. Best of luck to you Kristin!

  • Tiffany

    Everything was perfectly said. Most importantly I enjoy reading articles like these that are realistic and to the point. Thank you for sharing 🙂

    Today I decided to push my attention on one goal at a time. There are many things i want to do that fall under one bracket. Today for next 3 month focus on building one area at a time… already spent my 30 mins and hungry for more, until then ….

    I am not giving up!

    • That’s the exact attitude every entrepreneur needs Tiffany! Keep it up!

  • Aurorah

    This is so great for those entrepreneurs who are sitting on the fence. I walked away from corporate America in 2005 officially and never looked back. Congratulations on your year of doing your own thing and creating the life that you truly desire to live!

    • Thanks for the comment Aurorah! Always good to hear stories from the Foundr community, especially when they’re of happy entrepreneurs doing their own thing. Keep hustling!

  • Great post and timely. After just getting started, and slowly, I’m in a re-focusing phase. Nice discussion on Motivation, I’m trying to get up early to get more momentum flowing on workload. Also the trough of sorrow. Great encouragement!

    • Glad I was able to give some encouragement to you Quentin!

  • LillithBlackWriting

    Excellent article, THANK YOU! I’m in the same boat – building a new business while still working 9-5 (I even created a Facebook called Nightpreneur for people just like me!) Reading this article was like looking into my own head – all the hopes and excitement, and then all the fears and down days when I doubt myself. It was great to read that Nathan went through that too, and didn’t give up and now he is running a successful business.

    What I appreciated the most is that you mentioned that it takes a while to get business to the point where it’s successful, that it doesn’t happen overnight. So many out there talk about “instant success” and all that and this leads a lot of people down the wrong lane – they expect quick results and when they don’t get them, they give up. I would take realistic expectations over dreamy promises on any day.

    Thank you so much for this articles, it was great and all the resources are awesome!

    Lillith Black

    • Thanks for the comment Lillith! Will definitely check out your Facebook group.

      It’s really amazing how similar everyone’s entrepreneur journey is. But the result is always the same: the one who hustle and relentless work hard are the ones who are successful.

      Glad you enjoyed the article!

  • Leon Vo

    Awesome read… there were many things that resonance with me within this article. I appreciate how the author describe in detail the struggles of starting of uncharted waters as we make a transition from the corporate world. Thanks very much for your insight!

  • clevergirlfinance

    AH GREAT POST! I’m currently at the crossroads where i need to take that next step and give up my 9 to 5 to pursue my business full time. It’s nerve wrecking, scary and exciting all at the same time and of course the fear of failure is looming all the time. Thanks for posting this – definitely the motivation i need. I know I have a ton of work to get to success but i am SO READY!

    Instagram: @clevergirlfinance

  • Jan Nast

    Yup, I’m in the “trough of sorrow” stage and getting rather discouraged. Thank you for putting a label on it…that validates my feelings about where I’m at with my business, which is simple really. It’s all about my book, “Shifting to the Business of Life, A Survival Guide for Young Adults.” My husband and I sold our house, moved to a new state and in the process, lost my job. I gave myself 6 months to make it work, but now, after 2 months I’m thinking I have to go back to a full time job to ease up the pressure of making the business pay all the bills. Yikes! But, you give me hope and I need that. Thank you!

    • Always great to hear stories from member of the Foundr community

      Sounds like you’ve got the right attitude and I wish you the best of luck, and thank you so much for the lovely comment.

  • Belle Lockerby

    Great article, and good valid points, particularly the trough of sorrow, and remembering why. Getting feedback and seeing the difference you make brings its own rewards. For me, they are the things I need to remember when unwanted mental house guests fear of failure and self doubt come pay a visit. It’s the only way I get the buggers to leave!

    • Glad you enjoyed the article Belle! Like you said it’s comments and feedback like yours that keep me going when it comes to writing articles like these.

      Keep hustling!

  • That’s all it comes down to Thabiso. Keep hustling!

  • Danni Whittaker

    I’m 99% certain I am almost, almost, at the “promised land” phase 😉
    And I am getting closer to working on my own business full time and leaving FT employment; just working out the logistics!

    Thanks for reiterating things for me, you can try to convince yourself day in and day out to keep going (and you have to!) but to hear it from others on the same path definitely helps. Love following you on social media, love the realness and how you tell it like it is! Once I am out of my super povo stage (I’m launching an app – Fit Meet – 21 days to go! But development is not cheap. It’ll be worth it!) then I will definitely be signing up to your mag subscription. For now I am loving the budget friendly (free) info you put out, thank you! 🙂

    • Definitely glad I could provide some help for you Danni!

      Always great to hear how members of the Foundr community are doing and just want you to know that we’re definitely rooting for you! Keep hustling!

  • Kayode Tewe

    Great article! One thing I took out (amongst many others) is the importance of staying ‘hungry’. There should always be a desire to get to the next level, to grow. It’s what drives successful people. It’s what separates those who are successful from those who aren’t. Thanks for the write up.

    • You’re absolutely right Kayode, always comes down to having the right mindset and the mental toughness to push on.

      Glad you enjoyed the article 🙂

  • Beth Malatji

    Most brilliant article ever. You are so real. Keep it up

  • Most brilliant article ever. You are so real. Keep it up Nathan

    • Thanks @bethmalatji:disqus – But all credit goes to @disqus_pYZOHMKYCy:disqus for putting this one together. He did such a fantastic job!

  • Tom

    Brilliant write up and inspiration to keep going. Thank you

  • John

    Thank you so much for this inspiring article! It’s just the perfect kick in the ass that I needed. I particularly love the link on “overestimate the possibility of failure”. Absolutely brilliant! Thank you for sharing.

    • Thanks for lovely words John! Always good to know that all the research I put into these articles is worth it.

      Keep on hustling!

  • Xavier St. John

    The timing is perfect. Exactly what I needed. Thanks Jonathan!

  • Right on cue, it was only last night I finally decided to take action! Thanks guys, you’re the best!

    • Thanks so much for the comment. Stay inspired and keep on hustling!

  • Ari_Baiense

    Thank you for your wise words and reminders about the challenges ahead. I am still in the preparation phase and trying to avoid the analysis paralysis with so much information to digest and filter.
    I’ve been following several successful entrepreneurs around the web but it’s very hard to decide who we should pay attention to as I am a bit skeptical with the way some of them sell the idea of success. Personally it’s also difficult for me to see someone as a “mentor” but I don’t give up!
    As many here have said your words and Nathan’s experience are inspiring.
    All the best!

    • Thanks so much for the wonderful comment Ari! Best of luck on your own entrepreneurial journey!

  • Thanks for the comment Bola! Be sure to keep hustling 🙂

    • clevergirlfinance

      I’m working on it!

  • Glad you enjoyed the article Candis 🙂

  • All going well I won’t be in the, trough of sorrow, for too long 🙂 I’ve only been reading through your posts for just over a week or so, I have to say – I would have saved myself a lot of time if I didn’t bother with a business plan so early on, getting caught up in the technicalities before I refine my message and nurture my audience. Live and Learn.


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