Inside My Brain

Thoughts about startups, tech, marketing, and life

CATEGORY: Marketing

Building a movement is the best kind of marketing

One of the things I like best about marketing is how it can motivate people to take action and think differently about the status quo.

Online marketing has become so effective because you can measure nearly everything that someone does on the internet and spring upon them the perfect offer at the perfect time. And with all the behavioral data being collected by Google and Facebook, these transactions are getting easier to execute.

But they are just hard, cold transactions. Yes, they bring in revenue and profit, but most are lifeless and disconnected. There’s no real interaction with customers. Buyers find a product, enter their credit card info, click “Buy” and go bye-bye.

That’s why I admire brands that are built upon deeper relationships with its users. And the best brands create movements that develop these relationships not only between the company and customer, but also between customers to form communities of like-minded people. And these movements can be extremely powerful.

Here are some of my favorite examples of brand movements.

Dove Real Beauty

I am not at all the target customer of Dove’s Real Beauty campaign, but I love the movement that they have built.

Societal pressures have led us to believe that beautiful women can only be tall, skinny, and have perfect facial features and skin. Dove’s Real Beauty campaign looks to broaden the definition of beauty and give women of all ages, shapes, and ethnic backgrounds confidence in their appearance.

They’ve built an entire ecosystem around this idea by launching initiatives such as the Self-Esteem Project and giving women the ability to tell their own stories about beauty. This has allowed women to connect with one another, lean on each other, and build confidence together.

Movements can change how people perceive and define what’s around them, and act accordingly. And I think the Dove Real Beauty campaign does a great job of this.

Dove Real Beauty


Salesforce was the first Software-as-a-Service (where software is delivered via the internet instead of installed on your computer or in business’ data centers) customer relationship management (CRM) platform and they really built an amazing movement around “No Software.”

nosoftwarelogoAt the time of launch, which was around 1999, Salesforce’s competitors were companies like Siebel Systems and SAP, who sold client-server CRM and ERP software that had to be installed on-premises, which could cost hundreds of thousands of dollars and take years to implement.

That’s why Salesforce’s SaaS approach was so revolutionary back then.

The SaaS model would replace huge upfront costs with monthly payments over time, minimizing commitment fears. Software would be upgraded much more frequently at the same time for all users, alleviating the need for companies to bring in consultants to manually upgrade on-premise software every couple of years.

But because it was so different, the company had to really market the idea of “No Software” to convince prospective customers that moving to the SaaS model was the right thing to do. Salesforce’s CEO, Marc Benioff, was the head cheerleader of this campaign, and it helped build Salesforce into the $80+ billion software behemoth that it is today.


I’m a T-Mobile customer and I love what the company and its CEO, John Legere, has done to truly change the entire cell phone industry for the better.

T-Mobile’s “Un-carrier” movement has put its competition on notice and forced them to replicate many of their tactics.

Legere helped the company deeply understand mobile subscribers, how they used their phones, what services they accessed most frequently, and the pain points they faced. These are things that the other carriers neglected.

T-Mobile understands that:

  1. Taxes and fees can add a lot to your cell phone bill, and no one has any idea how much they will amount to. So they built these fees into the cost of their plans so you know exactly what you’ll pay each month. Transparency is powerful.
  2. Due to huge termination fees, customers were basically stuck in these two-year service contracts until they expired. T-Mobile was the first to do away with annual contracts and covered termination fees when a new customer switched from a competitor.
  3. They’re giving Netflix subscriptions for free! They actually want you to stream more content on their network.

All of these tactics truly put the customer front and center, and the “Un-carrier” movement has allowed T-Mobile to be one of the fastest growing major cell networks in the US.

The Past Two Presidents’ Campaigns

A presidential campaign is quintessential marketing. While awareness isn’t much of an issue, getting people to understand your “product”, compare it favorably to the competition, and take appropriate action is front and center.

And our current and past presidents launched movements that changed the course of our nation.

It pains me to say this, but our current President, Donald Trump, ran a very differentiated campaign that caused a huge movement among his constituents.

His mantra of “America First” led to a level of nationalism rarely seen before. “Drain the Swamp” conjured thoughts of all the corruption and incompetence in the Government and how he would clean it all up.

His campaign movement was based on hatred and lies, but it was a movement nonetheless that got him elected. Yes, he did not win the popular vote, but apparently he won the votes that counted. Ugh.

On to more positive topics…such as the campaign of our 44th President, Barack Obama.

Being the first African-American candidate to be nominated on a major party ticket is tough. Convincing the public to elect you as President would be even tougher.Barack_Obama_Hope_poster

Obama’s campaign represented “Change we can believe in” and a “Yes, We Can” attitude. It called for progress and hope for an improved United States. He needed the American public to think differently because he was so racially different than any other president in history.

And his team leveraged social media and other new technologies so effectively to spread the word and recruit evangelists.

The movement was certainly effective. Obama’s campaign convinced 63% of eligible voters to run for the voting booths, the highest in 50 years. And he became the first African-American President in US history.


Movements are powerful. They can galvanize communities and enact real change.

So whether you’re an entrepreneur, marketer, politician, or just someone trying to do good in some small way, try to find that angle where you can position yourself against the status quo.

Consumers want to be moved, and not marketed to.

What are other examples of movements that you’ve seen? I’d love to hear about them.

Let Your Personality Shine in Your Product

A couple of years ago, the folks at startup accelerator Y Combinator put on a series of lectures called “How to Start a Startup” at Stanford University.

My favorite lecture was lecture 7, “How to Build Products Users Love“, which was presented by Kevin Hale, Founder of online form company Wufoo and now Partner at YC.

There is a TON of great information about user onboarding, customer support, and much more.

But the enduring theme that I took out of the lecture was how to incorporate your personality into your product to make it something that your users love to use.

With Wufoo, they did things like include interesting microcopy, like having “RARRR!” pop up when you hover over the dinosaur login button:


Wufoo login microcopy



Another example was from one of Wufoo’s customers who included some hilarious microcopy in their sign-up form:

Corkd form microcopy


Every time you open Slack, they’ll have an amusing message waiting for you to start your day:

Slack quote


Of course, you need to build a product that provides value to the user, is fast, doesn’t crash all the time, has solid design, and has all of the other baseline things that a good product should have.

But these little user experience details count a lot, and incorporating your personality into your product wherever possible can delight users and keep them coming back. It can build trust, put a smile on users’ faces, and make them feel loved.

While product designs will differ, many products that do similar things tend to feel the same. There are many online form tools like Wufoo that get the job done. But the microcopy and other details that reflect the company’s personality can be the difference in winning or losing that customer.

Have you encountered a product where you saw the company’s personality shine through? I’d love to hear your thoughts!

Should you work on your weaknesses or focus on your strengths?

I recently listened to an episode of the podcast Seeking Wisdom where David Cancel and Dave Gerhardt from Drift talked about why you should forget about your weaknesses and focus on your strengths. Read the blog post here and listen/watch the video at the end after you finish reading this post. :)

This point of view certainly makes sense. It’s frickin hard to learn or get better at something that you’re not good at. And because it’s hard, you’ll also get frustrated when you make slow progress.

So maybe that time would be better spent on focusing on your strengths so you can turn them into superpowers, and delegating the stuff you’re not good at.

Here’s an excerpt from the episode’s blog post about one of David’s weaknesses:

For example: I’m not great at following up (especially with email). I’m a momentum maker. And that means I’m better at focusing on the here and now than I am at staying organized and creating process. But I used to fight it and I would focus on every single hack and trick to try and help — from to do lists on my laptop, reminders on my computer, phones on my phone, notebooks, etc.

This lesson took me a decade to learn. But eventually I learned the secret: I needed to double down on my strengths and surround myself (and team) with people who complement my weaknesses.

As a non-technical startup founder, it would be faster for me to recruit a technical co-founder or a contractor to help build the app. So instead of learning how to code, I could focus on customer development, marketing, and sales, all stuff that I’m much better at doing.

I do think there are situations where spending time on your weaknesses makes a lot of sense.

High-leverage activities

The first is if that weakness is a high-leverage activity that will have a substantial benefit if it’s improved.

In David’s example, being good at responding to email is a positive trait to have. But is it a high-leverage activity? Is it worth spending a decade trying to figure out how to get better at it? Or can David easily hire someone to help him respond to emails and be more organized?

On the other hand, for my situation, coding is a high-leverage activity that would benefit me greatly to know how to do.

Software developers are tough to recruit, but I was able to snag one on a contracting basis to help build WinOptix. Things are going great, but what if he decides to leave? I’d be shit out of luck.

And if we continue to work together, understanding how to code will allow me to 1) better estimate how long it will take him and others to build features of the product, and 2) contribute to the development of the product myself (eventually).

If your weakness is a high-leverage activity, it might make sense to put in the time to improve it.

If you don’t really like your strengths, enjoy working on your weakness, or both

Let’s say I’m strong at marketing. But one day I just get sick of writing blog posts, promoting them, running paid ads, and all of the other tasks that marketing entails. What should I do then?

The first thing I should do is assess my career. But what next? Should I continue working on my marketing skills, even though it kills me inside?

And let’s say I’m weak at programming (I am), but I looooooooove it (I don’t. It’s aight, but I don’t know enough to love it yet). Should I not try to improve my coding skills, just because I’m not really good at it?

Or what if both were happening at the same time?

Focusing on my strengths certainly wouldn’t make me any happier or necessarily better at my job.

Over to you

While I do see David’s point, there are certain situations where shoring up your weaknesses might make sense. I think the decision will be unique to each individual’s situation.

What’s your situation like? Are you focusing on your strengths, or working on your weaknesses? I’d love to hear from you.

BTW, David Cancel was an awesome guest on my podcast. Thanks David!

3 types of communities that are crucial for a startup’s growth

Communities have been an enduring theme on my podcast and have been crucial to the growth of many of my guests’ businesses.

While I’ve taken a break from podcasting, I continue to listen to past episodes and learn from my guests, and it’s no doubt how important communities are to their success.

Being involved with or building a community can be an extremely valuable way to engage with people who may later turn into customers, partners, and friends.

No matter what stage your business is in – whether you’re just brainstorming ideas or in the millions of revenue – there will be communities that can help move you ahead.

Let’s see what these types of communities are and how they can help.

Startup communities blog image

Local startup and industry communities

The first community that is very important when you’re launching a company is the community of startup founders, entrepreneurs, and industry professionals in your city or neighborhood.

For instance, if you’re a web designer in Raleigh, NC working on a financial technology startup, you should be part of and contribute to communities that focus on web design, fintech, and the general tech startup scene.

Being part of a local startup ecosystem can be a very powerful thing on many levels.

First, you’ll have a bunch of like-minded people with whom you can learn from and share your issues and concerns while you all are building businesses.

Regardless of whether you’re a solopreneur or part of a team, it’s always good to have an outsider’s perspective and an alternative point of view to solve your problem.

There is so much to do and to learn, and helping each other through the thick and thin is a valuable experience.

Next, you may be able to leverage your local network in order to gain customers.

Many of these entrepreneurs and small businesses are looking for products and services that you offer, and having that existing relationship gives you a foot in the door to make a sale.

You certainly want to add value before you drop the sales pitch on others, and being known as someone who gives before she gets is a great thing for business.

Finally, being part of the local entrepreneurship ecosystem opens the doors to many other networks, whether they are local or abroad, or directly related to your business or not.

By expanding your network, you may be introduced to future investors, partners, customers, and many others who may be able to help your business on one way or another.

If you’re a designer in search of a marketer, someone from your local network just may have a contact who is looking for that opportunity.

If your startup is ramping up and you’re in search for investors, a local entrepreneur may know just the person looking to make a bet.

As you can see, being part of your local entrepreneurial ecosystem can be extremely beneficial. But of course, it’s important to give before you get.

Volunteer your time at Meetups you’re interested in, provide some services for free, and be supportive of others in the community. Be known as someone who gives to the community and you’ll eventually receive benefits in spades.

Local communities are frequently spoken about on my podcast.

In episode 10, I chatted with Ron Schmelzer, the CEO of TechBreakfast, which is the largest monthly morning tech Meetup in the nation. If you’re into the technology scene, TechBreakfast events are great places to meet people like you.

In episode 14, Alec Hartman talked about how he is helping to grow New York’s tech scene by building TechDay.

In episode 16, founder Andrew Hyde and then CEO Marc Nager talked about how they launched and grew Startup Weekend to be a global phenomenon. Startup Weekend was one of the primary factors why I became an entrepreneur.

As you can see, there is no shortage of startup communities. No matter where you live, I’m sure that there will be a local startup or industry community waiting to welcome you, and being a part of these can pay off big time down the road.

Existing online communities

Existing online communities are the digital equivalent of your local community. The fundamentals of how they work are essentially the same, with the activity occurring on your laptop or mobile phone instead of in person.

Online communities will allow you to ask questions and garner answers from experts, provide your opinion and expertise to help others, make connections you wouldn’t have made otherwise, and potentially gain new customers.

But just like in local communities, you have to make sure to give before you receive. Blatantly promoting your wares won’t work, and doing so may get you banished from some of these sites. So make sure that you add value before extracting it from these online communities.

There are many community sites where you can interact with other like-minded people.

Reddit is the first to come to mind.


There are hundreds of thousands of “subreddits” (topic-based forums on Reddit), where people gather to share articles and discuss and debate different subjects.

Going back to that example of a web designer in Raleigh, NC working on a financial technology startup, you can join the r/web_design (153,000+ subscribers), r/startups, (109k+), r/fintech (1k+), and even r/raleigh (10K+) subreddits to have a huge built-in audience to engage with immediately.

For more info on how to market on Reddit, check out this post.

Facebook Groups are amazing resources as well.

When I started my podcast, I joined podcasting Facebook Groups like Podcasters’ Hangout and Podcast Community. I interacted with hundreds of fellow podcasters each day, learned from them, and picked up a bunch of listeners and reviews.

Quora is another great community in which to engage. Quora is the best question-and-answer site on the web, and many smart people ask and answer questions that span all kinds of topics. You can search for and share your knowledge about thousands of different subjects. It’s a great place to both learn and teach.

Build your own community

One of the best ways to engage your customers for a long period of time is to build your own community.

No matter whether you build your community in the real world, online, or both, you’ll have a population of people who want to hear from and engage with your content and offerings.

Again, the keys here are to offer value, give before you get, and don’t always sell.

In episode 1, John Von Tetzchner, the founder of web browser companies Opera and Vivaldi, built passionate communities around these web browsers.

At Opera, Von Tetzchner built the MyOpera community to a scale of 35 million visitors per month at its height. The users frequently gave feedback on the product, and many volunteers contributed their time to testing unfinished products.

At Vivaldi, John was able to build a community from many Opera users who shared the sentiment he did – that Opera was becoming more of a commodity browser and he believed that browser users needed something more powerful.

So he developed online forums that potential users could join to talk about what they wanted from a new browser. The company engaged this community and frequently asked them for feedback as they developed the new browser, which gave the community a sense of empowerment and connection.

In episode 12, Luis Congdon talked about how his private Facebook Group has helped him grow his podcasting audience and sell a lot of his product, a podcasting launch course called The Podcaster’s Secret Weapon.

I am a member of Luis’ Facebook group and I must say that he does a great job engaging and providing lots of value to his audience without being overt about selling his products. And even when he does push his products, he does it in such a way that helps his constituents.


As you can see, communities are critical to the growth of businesses.

Regardless of whether you’re just at the idea stage, in the process of building your product, or have sold millions in revenue, being part of or building a community can help you engage potential or current customers and partners and set yourself up for success.

What are some ways you’ve leveraged communities to move your business forward? I’d love to hear from you in the comments.

I hope you found this interesting! If so, please share this article with the share buttons on the left and then sign up for my mailing list below.

Thanks for reading!

Getting into the right frame of mind

All work isn’t created equal.

There are difficult tasks and easy tasks.

There are tasks that you can execute quickly and others that may take a long time.

Some tasks might require more brainpower or physical energy than others.

For some tasks – namely the difficult ones that require brainpower and may take a long time – being in the right frame of mind is crucial.

Take blogging, for instance. If I’m not in “writing mode,” it’s really difficult for me to crank out a blog post. I’ll procrastinate and the thought of writing will stress me out all day. And when I do sit down and write, it usually isn’t my best work.

Or working out at the gym. If my head isn’t into it, my workout will suck.

I’m not sure of the best way to get into the right frame of mind when I’m not into it.

Sometimes I’ll look for another less difficult task to execute.

Other times I just have to barrel through the original task and get it done. Many times that’s better than not completing the task at all.

Regardless, being in the right frame of mind makes things so much clearer and easier.

How do you get into the right frame of mind when you’re not in the mood to complete a task?

I’d love to hear from you. Write your thoughts in the comments, tweet at me @mikewchan, or email me at

I hope you found this interesting! If so, please share this article with the share buttons on the left. Then sign up for my email list below and connect with me on Twitter for future updates. And check out my podcast at!

My thoughts auto-DMing followers on Twitter

Automation is a powerful productivity concept that can free up time to perform additional tasks and saves on labor, materials, and cost.

For the most part, automation started in manufacturing, where processes were automated using a combination of machinery, hydraulics, feedback controllers, and eventually computers.

In marketing, software like Oracle Marketing Cloud (formerly Eloqua), Marketo, Hubspot and others help to automate the email marketing process.

These software packages can automatically fire off emails and other communications based on customer behaviors like joining a list, visiting a webpage, opening or clicking on an email, or not opening or clicking on an email.

Marketing automation saves marketers hundreds of hours of work and help engage customers and prospects at scale. But sometimes if it’s not set up right and delivers irrelevant messaging, it can hurt your brand.

Now that we’ve fully moved into the world of social, I’ve been experimenting with automation of engagement on Twitter.

Tools like StatusBrew and Crowdfire allow you to set up automated messages whenever someone new follows you. You can publicly send a mention to them or direct message them automatically (the latter being the more popular move).

I haven’t seen a big uptick in engagement for the auto-DMs that I’ve sent, which has me thinking that this isn’t really right for social.

But I have seen different types of automated messaging, a few of which really turn me off and hurt the brand of the user sending it. Here’s what I’ve seen and how they’ve made me feel.

The Auto DM with the name of the tool used

If you don’t pay for a tool like StatusBrew or Crowdfire, each of your automated messages will be tagged with something like “via” at the end.

This obviously tells the recipient the message was automated.

You’re trying to engage but you’re not trying to hide it. I won’t typically reply to these messages, but I’m pretty indifferent to them. No harm, no foul.

The obvious auto DM without the name of the tool used

When users pay for social automation tools, the “via” tag is not included. But many automated messages are written like they are obviously automated.

This turns me off a little bit.

If you have the ability to cover up the fact that you’re automating messages, you should at least put forth the effort to make it look like there is a real person sending the message, right?

Acknowledging the auto DM

Many people will acknowledge that they are sending an auto DM, with messages that say something like “Yeah, I know, this is an automated message, sorry! Automation is a necessary evil. But if you respond to this, I swear a real human will respond right back!”

I used this technique before I turned off social automation.

I’ve actually seen a slight uptick in engagement by sending these messages, and once in a while I would respond to the user who auto-sends me a message like this.

Being honest is an endearing quality that can help you better engage, and I think that’s at work here. It’s not ideal but it can work to a certain extent.

Saying “this isn’t an auto DM” when it really is

This is the absolute worst.

I’ve received messages from users who explicitly say that their DM isn’t automated.

How did I find out that it’s automated? Because if I follow this person with more than one social account, I receive the same message to all of those accounts.

And I’ve even been sent the same message multiple times to the same account.



The best thing to do is to manually respond to each and everyone of your new Twitter followers. But we don’t always have time for that.

I think that automation can eventually work in social media but the context analysis just isn’t there yet.

If you use automation, there are ways that it can be implemented where you can increase engagement. But make sure you take time and effort to do it right or else you can do more harm than good.

What are your thoughts about social media automation and auto-DMing followers? I’d love to hear from you. Write your thoughts in the comments, tweet at me @mikewchan, or email me at

I hope you found this interesting! If so, please share this article with the share buttons on the left. Then sign up for my email list below and connect with me on Twitter for future updates. And check out my podcast at!

Platforms vs. your website – interesting readership stats for my “Quality vs. Quantity” post

Two days ago, I penned a blog post called “Quality vs. Quantity – which should you focus on?“, which led to some interesting viewership results.

I published it on this site, Medium, and LinkedIn, as I do with most of my blog posts.

On, the post got 88 views and 4 shares.

On Medium, the post got 70 views and 2 “Recommends” (the equivalent of a “Like”).

On LinkedIn, the post got 1,683 views, 353 Likes, 86 comments, and 82 shares.

What the hell is going on here?

First of all, it’s not surprising that has such few views. I only have 40 people on my email list. And although I shared the article to 7235 Twitter followers, we know that only a tiny percentage of people see those tweets.

Ideally, it’s best to build a big email list, have direct access to those people’s inboxes, and drive as much traffic to your site.

But nowadays, with so much noise and so many people creating massive amounts of content, that strategy just won’t work on its own.

So you need platforms and networks to help get readership.

Yet I have no idea what happened here with the two platforms to which I posted the article.

I have 1100 followers on Medium yet only garnered 70 views. I have no clue how their algorithm works and how articles are distributed.

I have over 3300 connections and followers on LinkedIn. Having more followers will obviously drive more views, and the connections I have on LinkedIn are much stronger than those on Medium.

But nearly 25x more views than on Medium? And I got more comments and shares on LinkedIn than I did total views on Medium. I don’t get it.

The problem with platforms is exactly that – it’s tough to decipher how their algorithms work, your readership numbers are completely dependent on them, and they can change at any moment.

I guess I should get back to building my email list.

This is day 20 of my experiment to blog for 30 consecutive days.

Quality vs. Quantity – which should you focus on?

There’s a never-ending debate between quality and quantity, especially in my worlds of marketing and startups.

It’s hard to have both quality and quantity at the same time; they have an inverse correlation.

The more you do, the lower quality your work will be. The higher quality your work is, the more time it will take for each task, and you’ll complete fewer tasks.

So which is more important?

There’s a big debate about quality vs. quantity in the marketing world.

Content creation is a key part of marketing, and many companies try to pump out lots and lots of content so Google can index all of their articles and they’ll be higher on the search rankings. Sometimes this works, but it’s a grind and can cost a lot of time and money.

Then take SEO master Brian Dean. His blog, Backlinko, garners almost 120,000 unique visitors per month and a 7-figure income. And he has only written 32 articles in just over 3 years. That’s less than one blog post per month! He writes super-long articles that have a ton of value. That’s clearly quality over quantity. Not everyone can create these very long, in-depth articles, though.

Now let’s talk about the startup world.

Conventional wisdom says to do one thing and do it well. Hone in on a single problem, research it, perfect it, create a solution for it, and focus, focus, focus.

Then there is this guy who has launched 12 startups in 12 months. He built and tested a bunch of ideas to figure out what had the most potential.

Or there are venture capital firms that make only a few investments per year but focus on industries where they have expertise. Then there is 500 startups, who is playing moneyball and investing in a large number of startups (way more than 500) to diversify and spread out their risk.

It comes down to your particular situation, your mindset, what resources you have, and what you can execute.

I think there are pros and cons to each approach and you have to find the balance of what works for you.

This is day 18 of my experiment to blog for 30 consecutive days.

New experiment – 30 consecutive days of blogging

I’m going to blog for 30 straight days. Today, February 15, is day 1, and this is the first of 30 posts.

I’ve had this blog for a few years now but I’ve never been able to consistently create content.

There are plenty of reasons why, and here are some of them:

  • I’ve been busy with other projects.
  • I had a baby 9 months ago, and taking care of Maya requires a lot of time and energy.
  • There are times when I felt no one is reading what I write (which may be true), so I get discouraged.
  • (Insert any other reason here)

Actually, all of those are excuses, not reasons.

The real reason is that I’ve never dedicated myself enough to make blogging a habit.

With this experiment, I’m going to see if it can become a habit.

I recently listened to an episode of The Tim Ferriss Show where Seth Godin was the guest. Seth said that blogging was one of the best business decisions he has ever made, and that prompted me to start this experiment. You should definitely listen to that episode. It’s pretty amazing and really helpful.

What am I going to blog about for the next 30 days?


The posts are going to be about whatever is on my mind.

They may be about startups and my entrepreneurial journey.

Or my family and friends.

Or something random and interesting (to me) that I see that day.

These articles aren’t going to be fully though-out and researched pieces. Rather, this blog will be a journal or diary of sorts.

The posts probably won’t be the most grammatically correct, either. They probably won’t have any pretty pictures.

I don’t want perfection to get in the way of me just writing and publishing.

After 30 days, we’ll see where I stand and how I feel about blogging.

At best, I’ll continue to blog everyday.

At worst, I’ll develop a deep hatred for blogging and writing. I don’t expect that to happen, but it would suck if it did, because my livelihood depends on writing.

I hope you’ll come along for the ride with me. It should be fun. I hope.

Anyway, here goes! I’m hitting publish right now!

Do you regret your past career decisions? Here’s why you shouldn’t.

Career regret

Studies have shown that workers can have up to seven careers in their lifetime. If you’re one of these people, this means that you may have had to take a few steps back and completely start over with little experience in your new job or industry.

Thus, when thinking about your career trajectory, it’s easy to say “I wish I had done that sooner,” or “Man, if I knew then what I know now, I’d totally be killing it today,” or whatever else people say about the career and life decisions that they regret.

Many people who have made career changes wish that they realized sooner what they wanted to do with their lives. They think that they’re really late to the game and regret not doing things differently in the past.

My career has been a winding, swerving roller coaster, and I think this way sometimes. But it’s bullshit. And when I do think this way, I always call myself out, because things change all the time, and you never know how past experiences can help your current or future prospects.

Here’s what I mean.

My convoluted career path

I received my Bachelor’s Degree in Materials Science and Engineering in 2000 but had no desire to work in that field after graduation. After all, life wasn’t to be spent in a lab or steel mill.

Thus, I pursued my Master’s Degree in Industrial Engineering (IE) to hopefully start my career in the consulting industry. After obtaining that diploma in 2001 and getting a consulting gig, I wished I was interested in IE sooner. I felt that my four years of undergrad could have been better spent pursuing an IE major, and I wouldn’t have had to attend grad school.

Oh, regret.

The consulting career then ran its course.

When I started my career in sports business a few years later, I then wished that I had jumped into that industry sooner.

I was living the dream at my marketing job at the Washington Capitals. At that time, I couldn’t even imagine working in another industry.

Even when basking in the glow of my dream sports marketing job, I thought about how far up the corporate ladder I would have been had I started working in sports business after undergrad, instead of seven years and two graduate degrees (and lots of debt) later.

Oh, regret.

Until, of course, that career ran its course and I became an entrepreneur.

Do I wish that I had pursued entrepreneurship earlier in my career? Not at all.

You are the sum of your experiences

Your experiences make you the person you are now, and your current career is the aggregate result of your past careers. Even if your past careers seem completely disconnected from what you’re doing now, don’t ever regret the path you took nor take your past experience for granted.

I never came close to using materials science and engineering concepts in any of my careers, but that degree laid the foundation for the analytical thinking I use everyday.

I actually did use my IE degree in my consulting career, which is a plus. And even though I don’t directly apply IE to my current job, the concepts of efficient work, project and time management, and process analytics certainly influence each task that I execute on a daily basis.

And looking back, the MBA that I attained isn’t a necessary credential for an entrepreneur; rather, many say the degree is a detriment. But do I regret getting that degree? No way.

Although I attended NYU Stern to pursue a career in sports business, I learned so much about marketing, branding, and management, skills that I use every day. And much of my professional network stems from my time at NYU, which has helped and will continue to benefit my career in the future.


Sure, everyone wishes they had pursued certain career paths earlier, but hindsight is always 20/20. Don’t even waste time looking back and regretting your choices.

Just know that your past experiences make you who you are now, and that’s a good thing.

Your turn

Have you made career decisions that you regret? How do you think those decisions have impacted your career trajectory? I’d love to hear more in the comments.

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