Think Bigger

What to do when your new entrepreneur life feels out of control

People often overlook the emotional and mental struggles of transitioning from a 9-to-5 to the shapeless blob that can often be a beginner entrepreneur’s life.

When I first left my corporate job, I remember really looking forward to waking up without an alarm clock, taking three-hour lunch breaks, or even walking into a movie during the middle of the work day because I could — yes, I thought, this is “freedom”!

But reality dumped all over me like an ice bucket challenge.

I expected the freedom to do whatever I wanted, whenever I wanted, but what I got was me frantically flitting from one deadline to the next, too overwhelmed to budge from my desk, let alone leave the house. Sisyphus himself would laugh at my attempts to whittle down my to-do list, and it was a win if I didn’t end up putting my pants on backwards.

Ack, I thought I started my own business to have more free time…?

It took me another couple of months to slowly claw myself out of this hole. But it wasn’t because I started meditating in the morning or found an amazing productivity journal. It was the opposite of what I thought I initially wanted: I returned to more structure in my day-to-day to keep my DIY life from falling apart.

That’s right, the quest for more freedom begins with more structure, not less.

Don’t confuse freedom for flexibility

Life outside the walls of corporate life is not the “freedom” that lives in your fantasies. Rather, what it affords you is flexibility.

The flexibility to break at 2:15 p.m. to go for a walk or work out.

The flexibility to take days off without worrying about eating into your PTO.

But of course, there’s a trade-off.

If you don’t take steps to keep your burgeoning business moving forward, nothing happens. The business doesn’t grow. No money in the bank. Clients don’t know about you. And it wouldn’t be uncommon for your self-esteem to take a plunge and potentially get you sucked into a bad cycle of feeling sorry for yourself *looks around nervously*.

Worse yet, you don’t have the luxury of a team or someone to hold you accountable to your work or goals either.

Chances are, you probably know what you need to do, too, but knowing what to do and actually doing it are always at odds. If you have only yourself to answer to, who’s to know that you alphabetized your entire vinyl record collection instead of working on that business proposal or writing that sales page?

And that — the lack of accountability — is the fundamental difference between working in a full-time job within a corporate environment and being your own boss.

In an interview on, investor Paul Graham said it best:

“When you’re a child, your parents tell you what you’re supposed to do. Then, you’re in school, and you’re part of this institution that tells you what to do. Then, you go work for some company, and the company tells you what to do. So people come in like baby birds in the nest and open their mouths, as if they’re expecting us to drop food in. We have to tell them, ‘We’re not your bosses. You’re in charge now.’ Some of them are freaked out by that. Some people are meant to be employees.”

Graham is right. You’re not a baby bird waiting to be fed. You can’t afford to be, because you have a business to build and run.

That can feel disorientating at first, as if we were shoved from the nest and expected to fly right away. Part of the struggle of going at it alone after being in a corporate environment is that all of a sudden we’re not sure what to do or why we’re doing what we’re doing every single day.

“Show me a man’s calendar, and I will show you his priorities.”

I used to wing what I needed to do each and every day, but that led me to an endless merry-go-round of overwhelm and procrastination. Procrastination begot procrastination, where things took ten times as long to get done. I realized that the rigidity of a 9-to-5 kept me on track and accountable, even if I resented it at the time. So I needed to return to some form of that stability.

I started with planning out my weekly goals and auditing myself to see how I hit them to hold myself accountable. Before bed every night, I’d look at what I got done and move the items that absolutely needed my attention to the next day. This stability of knowing what to do enabled me to wake up knowing exactly what I needed to prioritize and perform at my best every day.

A well-kept calendar gives you clear direction. But of course, that begs the question: What if we just don’t “feel like” doing the thing? The feeling of not wanting to work is inevitably going to hit us some days. What then?

It’s not motivation you need

If you wait around for motivation to spur you to get into the nitty-gritty of building a healthy business, you’ve already lost.

Motivation ebbs and flows. Sporadic bursts of it will not build your business nor make it successful. Consistent work, done day in and day out, will.

To do this, it helps to first understand the difference between a “fixed” mindset and a “growth” mindset, concepts that were introduced by Dr. Carol Dweck, a psychologist from Stanford University.

To put it simply:

  • A fixed mindset emphasizes innate ability, as if you were just naturally cut out to be an entrepreneur. Your failures are a flaw in character, such as a lack of self-discipline or intelligence.
  • A growth mindset is a continuous push for self-improvement, a belief that a bad fall or failure is not a stop sign. You learn and keep going. Your success ultimately relies on improving different skill sets through deliberate (and often uncomfortable) learning, hard work, and experience.

To last as an entrepreneur, you need to develop a growth mindset. Things will be hard at first because you have no idea what you’re doing (that’s all of us!), but with a growth mindset, you recognize that you can and will get better, bit by bit. And that desire to constantly be better reinforces a positive feedback loop that helps you summon motivation from within yourself to do the work on a daily basis, whether you “feel like it” or not.

Because the reality is, you won’t love every minute of what you’re doing — like doing your taxes or dealing with irate, rude customers. Otherwise, who else but you will get them done?

Using structure to your advantage

So if we can’t wait for ourselves to “feel like” working and it’s hard to hold ourselves accountable, then what we might need are a consistent routine, boundaries, and an overall structure. This is the paradox that new entrepreneurs must face: That they left the corporate world to avoid structure and so that they could do things on their own, on their own terms; but eventually they need to come back to the stability that structure affords them in order to thrive in their business and personal life.

What that structure looks like, however, is going to be different for everyone, but structure benefits you for a few reasons:

  1. You rely less on willpower and free up mental energy for the important things.
  2. You have more control because a side effect of entrepreneur life is that it’s too easy to feel out of control.
  3. You know what to expect every day, so you can stay one or five steps ahead of most things before they overwhelm you.

A structure isn’t necessarily a routine (though having one can help). Rather, structure here refers to intentionally placing constraints on yourself.

Constraints function both as ways to help you stay on top of meaningful, productive work (none of this work-for-five-minutes-then-check-Facebook stuff), but also to set boundaries so that you still have the flexibility to do the things that recharge and fulfill you. A few ideas on constraints:

  • Choosing only one or two of the most important tasks of the day (that you would actually be happy that you finished) and sticking to those.
  • Imposing time constraints on certain websites. Tools like StayFocused and KeepMeOut can lock you out of time-sucking websites like Facebook and YouTube.
  • Working in 30-minute batches. It’s nearly impossible for anyone to stay fully productive for hours on end, but doing focused work for 30 minutes? Sure, that’s manageable! This is a slight riff on Tomato Timer, which encourages you to work in 25 minutes spurts — same thing. Thirty minutes is just a nicer, round number.

By placing constraints, you force yourself to do better work when you DO work and get creative. Simply, constraints beget creativity and creative solutions. Think of Vine, the now-defunct social media platform that allowed only six-second videos. Six seconds is not a lot of time for cerebral videos, but some creatives have been able to produce the most compelling, damn entertaining videos in just six seconds, like this one.

While imposing these constraints is a good way to help you do more meaningful work without getting caught in an overwhelming frenzy, it’s also important to place constraints on when to STOP working.

In other words, the constraints on your day should be to set start and stop times that you stick to on most days.

Structure isn’t binary. It’s a spectrum. You simply have more (like in corporate life) or less (life as an entrepreneur).

The moment you quit your job you don’t get to spend unending time on a beach. Just like taking a 9-to-5 job does not chain you to a desk for 20 hours a day. You started a business to calibrate your working life for what works for you. You get to pick the right amount of structure. Not some person up in the org chart.

Just keep at it, not expecting yourself to “get” everything immediately, and make adjustments as you need to make your newfound flexibility rewarding for you. I promise it’s worth it.

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One Comment


Great article, Stephanie!

The lack of accountability is so real, any quick ideas on how to work on them and build it so we have that built in?

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