How to swap your job for your side hustle

Helen Tupper, co-founder of a career development business, Amazing If, swapped a successful corporate career at Microsoft to transition her side project into a full-time job. Here Helen shares what she’s learned about career progression and the opportunities of going it alone. Rebecca Ley reports. 

Career history

  • Board trustee, Working Families (present)
  • Co-founder and CEO, Amazing If (2013 to present)
  • Commercial marketing director, Microsoft (2 yrs 1 month)
  • Head of marketing, Virgin Red, Virgin (3 yrs 1 month)
  • Global head of customer experience and thought leadership (Castrol B2B), BP (1 yr 8 months)

You set up a side project, which has since become your business and full-time role. How did that all start? 

I was reflecting on my career since university with a friend (and now business partner), Sarah Ellis. We thought we’d have this really predictable linear career and would be really motivated to get to the top of the ladder. The reality was that career path was less like a staircase and much more squiggly. I’d done B2C and B2B marketing, I’d done sales and worked in financial services. There’d just been much more movement than I expected but I’d loved that. 

For us, a happy, successful career isn’t about being the most senior person in the business, it’s about learning, developing and exploring. We noticed that other people identified with this but didn’t feel so positive about it. We thought it would be amazing if we could make that work better for everyone.
That’s when our business, Amazing If, started. As naturally creative marketers we questioned what skills people need most to succeed in a squiggly career, and how we could help develop them. We both had a passion for helping people learn and develop and felt that we could do more than we were doing in our jobs. 

Aside from delivering career advice to individuals, you also partner with companies. How do you help them?

Lots of organisations are struggling to help their employees develop in their career, because they think development is climbing the ladder. But organisations are offering fewer promotions because they’re becoming flatter. What they really want is employees who can take ownership of their career development and not just in a linear way.

How did you balance your side project with a full-time marketing career? 

I started Amazing If in 2013 alongside my marketing job. I did that for six years before I left corporate life to scale my side project. 

The company got big enough that it was a viable alternative as my job. It wasn’t supposed to become a business. I’ve just focused all of my time on what I love the most and where I’ll have the most impact. That’s been my filter. 

I was working as head of marketing in the management part of Virgin when I set up Amazing If. Virgin was so supportive because it’s part of their DNA to be entrepreneurial and try things out. They totally embraced it and doing it helped me be more creative and gave me more ideas. If you look at research on side projects it’s clear that rather than be a threat to the day job, it helps make somebody more creative and passionate. When I later joined Microsoft I was really transparent about having this business.

Giving up a successful career to pursue this new venture is a risky but exciting decision. What made you do it? 

After Virgin I moved Microsoft and left my role there as Commercial marketing director last year. I loved my job at Microsoft but Amazing If became bigger than a side project and I had to make the choice to scale it back or just go with it. 

I was using all of our holiday to run Amazing If and it was a bit mad. I have a four-year-old and two-year-old, which I didn’t have when I started, so I couldn’t use my holiday for my side project anymore. 

But more than the practicalities of it was the passion I had for it. It got to the point where the most inspiring emails I got each day were from people who’d been on our courses three years ago and wanted to share the impact of it.  I thought ‘wow, this is actually really fundamentally helping people’, and I wanted to do more of that.

What advice would you offer to someone setting a ‘side hustle’?

The first thing would be to prioritise. What I notice running my own business is that there are so many distractions. I have far more ideas than the size of the company. It’s crucial to prioritise and focus on what’s most important and impactful right now. 

Reputation is also really important, if you commit to doing something for clients on a certain day, commit to doing it. Also enjoy what you do. You’ve made the choice to move from a corporate career to running your own business, so if you don’t enjoy what you’re doing every day then change it. It’s in your power to. 

Is it better to go it alone or with a partner? 

Find someone to do it with. It’s very useful for support and also you’re not going to be great at everything. Starting up with someone else meant when my work at Virgin became high pressured, Sarah could pick up what was happening at Amazing If.

If you’re going to do it with a friend, you have to create an environment between you where you’re comfortable giving each other feedback. There’s more emotion sometimes with a friend and just in the way you have structured feedback at work, you need structure with a friend as well. Sarah and I give each other feedback almost every day.

Did your marketing skills help you grow your business?

Yes, 100%. Having a marketing background is so helpful when you start a business, because you think about the customer from the outset. I think about who we’re targeting, who’s the audience, how I find them, how I engage them and what the customer journey is like. It’s just innate in my thinking. 

How I build the brand and have a consistent tone of voice is such a big part of building an audience. It’s the DNA of the brand and having a marketing background means I don’t have to outsource it. 

What’s benefited you most in your career?

Three big things have helped me - including a couple of brilliant managers who were specifically very good. They gave me jobs I couldn’t do yet, they stretched me and supported me, they advocated for me and helped me do courses and connected me to people. 

The second thing is my network, particularly the Marketing Academy, which was very useful to me. It’s a community for CMOs and mid-level marketers with ambitions to be CMOs, it’s a fully-funded scholarship with a cohort of 30 people. You get an executive coach and get mentored by CMOs. That community grows every year, and it’s now in Australia and New York. 

The last thing is coaching. I’ve had various coaching that really helped me to learn and develop and reflect. Those things were pivotal in my career. These things all helped me with Amazing If.

Do you have a plan for where you want Amazing If to go next?

I want to scale in a sustainable way. That means staying true to our values as a business. We don’t have a master plan because that hasn’t been what’s worked for us to date. We’ve been successful because we’ve let it grow organically and kept it focused on career development.

What factors are most important to your job satisfaction and success? 

I think belief in the vision and direction is most important. If I don’t believe in where we’re going then the best team in the world and all the autonomy they can handle doesn’t matter.

I also think emotional intelligence is vital, particularly in stakeholder management. You’ve got to find sponsors and sources of influence or you’ll be flying blind. Your EQ is fundamental in building those relationships.

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