Diana Elizabeth lifestyle blogger wearing Sunday best: Banana Republic white lace midi pencil skirt with Parker tunic-fit tie-cut shirt

Questions about leaving corporate + being an entrepreneur

Talking about leaving corporate answering Q&A //Diana Elizabeth lifestyle blogger wearing Sunday best: Banana Republic white lace midi pencil skirt with Parker tunic-fit tie-cut shirt

There were many questions asked after I published this post about my in-depth story about leaving the corporate world and pursuing full-time self employment. I answered a few on IG stories and thought I would take those questions and answer them here more in depth.

I know it’s scary to leave something secure and I think there are many factor that you should consider before leaving but everyone has their own journey. You’ll know when you are ready. Meanwhile, I am happy to answer any questions you have, just leave a comment and I’ll get back to you.

Do you miss the corporate office environment?

Sometimes! I enjoyed working in a big office and seeing coworkers. It was always fun to dress up, do your hair and makeup and show off a cute outfit to your girlfriends. There’s also excitement about working for a large corporation and walking on the studio lot of into headquarters.

I am a people person and I love girlfriend so I miss certain things about the office environment. Like teamwork, meetings, and just being able to chat with friends. Of course not every office has a fun culture but very office I worked in was incredibly fun and I looked forward to work. I mean, until I decided I wanted to work for myself of course.

How do you save for taxes?

The general rule I heard was save 30% of what you make for taxes. I did that in the beginning when I was still building my business and my business bank account.

Now I don’t really think about it at all because I have a padded bank account (I mean a minimum that taxes can definitely be deducted from). So I know I have plenty at the end of the year. Benjamin likes to joke how I save for taxes is I got married (eye roll).

I recently started contributing to a SEP (Simplified Employee Pension plan) which cuts down the taxes I pay because what I contribute is deducted from my income, like a charity but to myself.

I obviously can’t touch it until a certain age without a penalty if I withdraw earlier. It is how I save for the future like a personal 401k.

Would you ever go back to corporate?

Never say never. It would have to be for the right price, or the perfect job. I would definitely go back if I needed to financially for personal reasons or whatever. I wouldn’t think it’s a bad thing to go back to the corporate world if it’s the right time.

There’s wisdom in knowing what is best for you and your needs.

What characteristics do you think a person needs to be a successful entrepreneur?

  1. A hustle mentality. It’s sink or swimsuit being self-employed. It’s all on you.  Be hungry and take any and every job in the beginning as you are growing your business and you have to squirrel away money. You just work so hard because you don’t know when your next pay check is coming.
  2. Be disciplined. Work hard and push yourself and also save money! You have no 401k from work and saving for the future is a must on your own. If you claim no income (taking only cash) you are negatively affecting your future of social security (you either won’t get any or way less). Don’t do it!!
  3. Love people. You have to network and so being outgoing and loving people and having the spirit of connecting is helpful. You need to meet with people to connect, get referrals and also help others so work comes back to you. Entrepreneurship is not just you, it’s a community.

How did you find health care as an entrepreneur?

Since I was single and over the age of 26, I couldn’t get back on mom and dad’s insurance. One of my best friends Brenna told me her godfather was a health insurance broker and he helped me with several health care options. I never understood healthcare until it was in my own hands.

Since I was young and healthy and wasn’t sure how much money I could actually afford, I picked a high plan deduction, like $15k.

I know that sounds insane but I figured $15k wouldn’t put me in the hole and I wold have to be seriously sick. I don’t suggest this, but that was what I did and I paid about $100 a month for coverage. I figured if I made more money I would go to a better plan.

I obviously got married so I’m on my husband’s insurance plan now. It makes it a lot easier in many ways but that’s how I did it as a single gal!

Do you focus more on photography or the blog now?

This year finances say the blog. Last year it was about even with income from both. Right now I spend about a quarter of my time on photography assignments. They are primarily from Phoenix magazine and Phoenix Home & Garden, or corporate referrals. I don’t market my photography on social so what you mainly see if blog related. I’m definitely still photographing (I prefer to have several sources of income). I feel like I still do photography like every day for the blog.

I still love both. Because I still love money.

How do you stay disciplined to find work?

I put it on my calendar weekly to reach out to brands and check in with my contacts. It’s always important to be on friendly terms with everyone – some friends send over work.

I also make sure I blog 3x a week to stay active. Blogging is tough, if you stop doing it, you’ll just stop. You have to be in good practice to just write and put out content because it’s all about discipline. If you want to be a _______ then ________. Like if your want to be a photographer, keep taking photos and sharing it. If you want to be a blogger, keep writing and publishing blog posts.


To read my story about how I left corporate America and how I adjusted, read this post.

Have you left Corporate America? Please share your story. Questions on entrepreneur life? Ask in the comments.

Diana Elizabeth is an author, photographer, and obsessive thrift shopper. You can typically find her in the garden wrist deep in dirt, at a local estate sale or planning her next epic party. She continues to blog weekly.


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