Getting Started

How I launched my own business — and got my boss to pay me to do it

This past June, I celebrated a very special anniversary: Three years. Three years since I walked into my boss’s office and told him, “No, I do not want to be on the fast track to VP.”

Crazy, right?

Well, not really…

When I’d taken the position as HR manager for a subdivision of a Fortune 500 manufacturing company in 2010, I had been upfront with my hiring manager.

I let him know that while I was completely committed to doing a top-notch job for the company, my end game was to launch my own business. I had given him a seven-year time frame. Now I was telling him that seven years had shrunk to more like four or five.

He looked at me with a hint of disappointment in his eyes, took a deep breath, smacked his hand on the desk, and said, “How can I best support you?”

I was on my way to negotiating a sweet deal. One that would allow me to keep my current position and title while significantly reducing the amount of time that I spent in the office and the total hours I worked — without losing a penny of my salary.

After that conversation, everything changed. I was able to carve out the needed time to build my business without stealing from my family and still maintain my workload (and income).

By the time I quit in December 2015, my business, Happen to Your Career, was bringing in about $7,000 a month. Just a few months later, we earned $16,584 in a course launch. Now we’re on track for our best year ever, aiming to break $200K in 2016.



My success in negotiating with my employer was a direct result of using a very specific process. I didn’t know in 2010 that I’d someday be asking for unheard-of job flexibility. But looking back, I realize that they agreed to my request because of habits I developed from my first day on the job.

Because it was a specific process, you can follow the same steps and see similar results. Here’s how you can get your current boss to agree to give you the flexibility you need to build your side-hustle.

Step 1: Make them love you

When you’re trying to get someone to do something they’ve never done before — let you begin working from home, job-share, take a sabbatical, work fewer days — the most important factor is: Does your boss trust you?

If the trust isn’t there, your chances of success are pretty slim. After all, if you’re not getting your job done while sitting 20 feet from your supervisor, why would they agree to let you work from home?

By the same token, if your boss knows you do what it takes to get the job done, you deliver consistently and on time, and are a team player, they’re going to be much more open to working with you.

As I mentioned above, I was up front during the hiring process about my intention to start my own business and eventually leave the company. While my boss wasn’t aware until I told him that the timeline had changed, I had never hid my intent from him.

That complete transparency won a lot of points, as he knew me as someone who was open and honest.

Also, over my years at the company, I met with my boss on a weekly basis, reviewing what I thought were my priorities and aligning them with what HE saw as my top objectives.

That meant that not only was I recognized as a hard worker, I was also seen as a major producer since the projects I worked on were the ones my boss perceived as high-value.

Because he trusted me and I’d built a reputation of integrity, I wasn’t hesitant to make a “big ask.” I had proven my worth.

If you’re a great employee, you may just need to up your visibility and tracking a bit. Start meeting with your boss more regularly to check in on his priorities and make sure you’re working toward those, not what you think he or she wants you to do.

If you haven’t been “Employee of the Month” material, now’s the time to adjust. Pay attention to the little things, like getting to work on time, turning in projects or assignments when you say you will, going above and beyond when you can, and in general being a superstar.

Bosses notice even the smallest shift in attitude and effort. See all of this as an investment in your future company.

Step 2: Ask so you are sure to receive

Most people are hesitant to ask for something beyond the norm, but if you don’t ask, you’ll never know what you could have received.

Anything is possible in a negotiation. You just need to ask the right person (who) at the right time (when) and the right place (where), and know your end goal (what).

Knowing those four elements and presenting your plan in a way that benefits the person you’re asking are the keys to success.

In my case:



I let my bosses know that allowing me to test out telecommuting would help cement the company as an accommodating, flexible place to work (something employees highly value).

Also, I explained that working from home — even for a few hours a week — would make me much more productive. I would be able to concentrate on big projects without being interrupted with constant “fly-bys” by co-workers “just checking in” or asking me to attend unnecessary meetings simply because I was around.

In addition, I offered to work an hour longer a few nights a week if it was needed to complete my regular workload.

By being willing to start small and present the idea as a “test,” I got the agreement to move ahead with a small version of my plan. I didn’t get a full day every week, but I got a half-day every other week to start, with the commitment to revisit expanding that time after a month if the trial was successful.

Maybe it’s not telecommuting you want. Maybe you want to take a three-month sabbatical to attend a yoga certification program, or the ability to leave work early on Wednesdays and Fridays to take a continuing education class.

Whatever your end goal is, you’ll be more successful if you formulate your “ask” properly. Think about the four key elements:



Step 3: Prove them right

The best reputation and the greatest negotiating skills in the world won’t help if you don’t follow through on what you agreed with.

You need to perform and meet — or hopefully exceed — your commitments and keep your supervisor(s) in the loop so there are no surprises.

I wanted to show my manager that I was keeping connected with the team, keeping up with my regular responsibilities, and getting even more done.

Before a day out of the office, I’d notify relevant contacts within the company when I’d be out, for how long, and how they could reach me in case of an emergency. (No one ever did!)

I also focused on completing some projects of particular value to my boss that had been falling to the bottom of my to-do list. This showed him that I was not only keeping up, but I was getting more done.

Finally, I kept track of some pertinent metrics, like number of interruptions and time spent in meetings. I compared my performance before telecommuting and after to demonstrate an increase in productivity.



Using this system, I noted one day when 10 out of 13 interruptions were for chatting, NOT needs.

As a result, not only did I get permission to continue telecommuting beyond the four-week trial period, the half-day every other week was soon expanded to a half-day every week, then a full day every week.

In the last three months, “working at home” became a whole day off per week, as I was keeping up with my formerly 50-hour-a-week job in less than 30 hours.



Working from my living room “desk”

You should already be clear on your priorities from your regular meetings and check-ins with your boss. Now you have to prove to them that you’re not only meeting, but exceeding their standards in key areas.

If your boss is revenue-driven, show how you’re able to generate more when you’re telecommuting. If he or she wants to feel like they have anytime access to you, make sure to answer their calls and emails immediately.

But by all means, if the situation isn’t working, be up front about it. No fudging the data to make it look better — that’ll get you a one-way ticket to the unemployment office.

What do YOU want?

Oftentimes, we think of employment as an all-or-nothing deal. We’re either employees or entrepreneurs, with no grey area in between. I hope that my story opens your mind to all sorts of possibilities by showing you that there is room for creative thinking and negotiation in your day job.

If you’re a valuable employee who has consistently shown your worth, you know what you’re trying to achieve, and you ask the right person at the right time and place, nothing is off the table.

Being willing to “make the ask” in the right way enabled me to invest an additional 5-7 hours a week on my business, which led to generating $34,458.

While I enjoyed my job, I always knew I was meant to be an entrepreneur. I love the freedom and greater income my new lifestyle affords me and my family. But more than anything, I love the flexibility to be more present with my family.

This hit me really clearly right after I left for good in late 2015. It was 10 on a Tuesday morning, and my kids and I headed outside to hang up our Christmas lights. I remember thinking, ”Last year, I couldn’t have done this! I’ve never put up Christmas lights before — let alone on a Tuesday morning when everyone else is at work!”



It might seem like a small thing, but to me, that ability to spend time with my kids, just doing everyday life together, is what it’s all about.

Now, what I’d love to know from you is two things:

  1. What would be the perfect work arrangement for you right now? What would you love to ask your current boss for, but you’re afraid they’ll say no?
  2. How would granting your wish make your employer’s life better or easier?

Once you’ve answered those two questions, you can negotiate anything.

Leave your answers below. I’ll be watching the comments and responding to your questions.

There Are 12 Comments

Join The Conversation

This is a great article and I love the 3-step approach: earn trust, ask, and fulfil your end of the deal. It doesn’t seem that complex, but it’s amazing to me that the vast majority of people will never attempt this because they are afraid to ask or don’t know what they want.

This is an awesome story and I respect how long you built this thing on the side because that takes a ton of discipline and focus on your “why” being able to negotiate these terms with your boss was huge because most people are afraid to have that level of authenticity with their boss.

Thanks Olivia! Appreciate it! It’s taking a small risk. But the potential rewards are huge! I didn’t get nominated for the really cool company trips near the end, but I was totally ok with that! I know you’ve got a pretty good story too! 😉

This is a great article! I love how you were able to systematize a process that can seem so daunting. However, in your admirable humility, you’re leaving out one crucial key to your success – you’re REALLY REALLY GOOD at what you do.

I have had the pleasure of working with Scott as a client and he regularly over delivers on his value proposition. He’s taken my business from $0 to having a $3k + month within two months of working with him. He’s incredibly knowledgeable, helpful, and personable. It’s been a pleasure working with him and I’m glad to see his teachings proliferating online.

Keep up the great work, Scott!

Excellent article Scott! It’s an important point to be cognizant about how having our wish granted would make the employer’s life better or easier and to approach it from that perspective/angle. Thanks for this reminder!

Hey Scott

Love this article! Could not have read it at a better time. I work for a small education start up. It’s awesome, but the past year or so have stressful and exhausting and has had no prospect for a pay rise. I recently spoke with my new boss that I didn’t see myself being there next year and even if they had something to offer me, I doubt I’d take it. However, they paid for me to go through certification on the current platform I’m working on and after than conversation she asked me, “What could I have done to keep you?” I replied with, “It would have been great if you were here 6 months ago”.

The truth is, she is great, the team is great, but what I really want is a pay rise, and 1 day less hours so that I can launch myself as an artist. I’ve been taking on opportunities – doing shows and markets and it’s more costly than lucrative right now. However, if I don’t take the plunge, how will I ever?
I made it clear that I need a path to get where I want to be, but should I give this job another chance? Or go through the trouble of finding another one that pays better, but will have to start over again building relationships?

Hey Scott, Love this article! Could not have read it at a better time. I work for a small education start up. It’s awesome, but the past year or so have stressful and exhausting and has had no prospect for a pay rise. I recently spoke with my new boss that I didn’t see myself being there next year and even if they had something to offer me, I doubt I’d take it. However, they paid for me to go through certification on the current platform I’m working on and after than conversation she asked me, “What could I have done to keep you?” I replied with, “It would have been great if you were here 6 months ago”.

The truth is, she is great, the team is great, but what I really want is a pay rise, and 1 day less hours so that I can launch myself as an artist. I’ve been taking on opportunities – doing shows and markets and it’s more costly than lucrative right now. However, if I don’t take the plunge, how will I ever?
I made it clear that I need a path to get where I want to be, but should I give this job another chance? Or go through the trouble of finding another one that pays better, but will have to start over again building relationships?

Scott, telecommuting is something I get to try every now and again with my current employer. And I couldn’t agree more with you that it makes me more productive. As you showed in your tracking spreadsheet, on one day, 10 out of 13 interruptions were for just chatting with you. I find that tends to be the biggest distraction at work. Also, I’ve noticed that when I’m not around and people have questions, they tend to figure out the answer anyways. It seems coworkers are looking for the nod of approval that their decision is right before they implement something.

Like you, I too am building a side business. I’ve gone back and forth about how to approach my employer and tell them that this is something I want to do full-time once it gets big enough. I’m constantly nervous that if I have that conversation, I will be in the unemployment line, as you said. Part of me wants to tell my employer, but everyone I talk to says not to do it and wait until I have enough clients to leave and work full-time at my business. It’s a definite risk to bring it up given that I’m only a year into my role.

What would you suggest in this case?

I couldn’t agree more with you that it makes me more productive. As you showed in your tracking spreadsheet, on one day, 10 out of 13 interruptions were for just chatting with you. I find that tends to be the biggest distraction at work. Also, I’ve noticed that when I’m not around and people have questions, they tend to figure out the answer anyways. It seems coworkers are looking for the nod of approval that their decision is right before they implement something.

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